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Critical Reviews in Food Science and Nutrition
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Sucrose fatty acid esters: synthesis, emulsifying
capacities, biological activities and structure-
property profiles
Yinglai Teng , Scott G. Stewart , Yao-Wen Hai , Xuan Li , Martin G. Banwell &
Ping Lan
To cite this article: Yinglai Teng , Scott G. Stewart , Yao-Wen Hai , Xuan Li , Martin G. Banwell
& Ping Lan (2020): Sucrose fatty acid esters: synthesis, emulsifying capacities, biological
activities and structure-property profiles, Critical Reviews in Food Science and Nutrition, DOI:
10.1080/10408398.2020.1798346
To link to this article: https://doi.org/10.1080/10408398.2020.1798346
Published online: 04 Aug 2020.
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REVIEW
Sucrose fatty acid esters: synthesis, emulsifying capacities, biological activities
and structure-property profiles
Yinglai Teng
a,b
, Scott G. Stewart
c,d
, Yao-Wen Hai
a
, Xuan Li
a
, Martin G. Banwell
a,d,e
, and Ping
Lan
a,b,d
a
Institute for Advanced and Applied Chemical Synthesis, Jinan University, Zhuhai, Guangdong, China;
b
College of Pharmacy, Jinan University,
Guangzhou, Guangdong, China;
c
School of Molecular Sciences, The University of Western Australia (M310), Crawley, Western Australia,
Australia;
d
Research Laboratories, Guangzhou Cardlo Biochemical Technology Co., Ltd, Guangzhou, Guangdong, China;
e
Research School of
Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, Australian Capital Territory, Australia
ABSTRACT
The notable physical and chemical properties of sucrose fatty acid esters have prompted their use
in the chemical industry, especially as surfactants, since 1939. Recently, their now well-recognized
value as nutraceuticals and as additives in cosmetics has significantly increased demand for ready
access to them. As such a review of current methods for the preparation of sucrose fatty acid
esters by both chemical and enzymatic means is warranted and is presented here together with
an account of the historical development of these compounds as surfactants (emulsifiers). The
somewhat belated recognition of the antimicrobial, anticancer and insecticidal activities of sucrose
esters is also discussed along with a commentary on their structure-property profiles.
KEYWORDS
Biological activities;
chemical and enzymatic
synthesis; emulsifying
properties; esterification
and transesterification;
structure-property profiles
Introduction
The disaccharide sucrose (b-D-fructofuranosyl a-D-glucopyr-
anoside), commonly called table sugar, is obtained from
various plant sources, is easily refined and is marketed
world-wide. Global production of this compound reached
ca. 180 million metric tons in 2016/2017 (Canadian Sugar
Institute 2019a). Direct consumption (as a food) accounted
for most of the demand but sucrose is also employed as a
starting material in the production of emulsifying agents,
detergents, artificial sweeteners and various other derivatives
(Human Metabolome Database 2019). Sucrose, which is
photosynthesized by almost every green plant but is most
readily derived from sugarcane and sugar beet (Canadian
Sugar Institute 2019b), is also exploited in the production of
ethanol and certain fine chemicals (Deneyer, Ennaert, and
Sels 2018) including sucrose fatty acid esters (Neta, Teixeira,
and Rodrigues 2015).
Sucrose fatty acid esters, as with esters more generally,
are formally derived from the constituent alcohol (viz.
sucrose) and (naturally occurring) fatty acid. Notable
commercially available forms of such esters include the
mono-esters derived from, inter alia, steric acid, palmitic
acid, lauric acid, oleic acid, erucic acid and myristic acid.
These esters, which frequently come as admixtures with
various of their di-, tri- and tetra-acylated counterparts
(Mitsubishi Chemicals 2019; Sisterna 2019a; Sisterna 2019b),
have excellent emulsifying properties as well as a range of
other useful physical properties that follow from their
amphipathic nature (Szuts et al. 2010; Farr
an et al. 2015;
Soultani et al. 2003). Importantly, such nonionic surfactants
are considered green because they are both nontoxic and
biodegradable. Furthermore, both the constituent sucrose
and fatty acid residues are inexpensive and renewable agri-
cultural products (Szuts et al. 2010; Farr
an et al. 2015;
Soultani et al. 2003). These various attributes mean that
sucrose esters have become profoundly important commod-
ity chemicals in the food (common ingredient number E473,
according to Food Standards Agency 2018), nutraceutical,
cosmetic, dental and pharmaceutical industries (Szuts et al.
2010; Farr
an et al. 2015; Soultani et al. 2003). Even a decade
ago, the world production of sucrose esters was estimated to
be above 6000 t/year and these were selling for 4 to 20
USD/kg. While mainly employed as food additives, they also
feature in the manufacture of cosmetics, pharmaceuticals
and detergents (Otomo et al. 2009). In 2015 the global
sucrose ester market was valued at USD 55.7 million and
projected to reach USD 74.6 million in 2020
(MarketsandMarkets 2019b). Key manufacturers of these
now much sought-after community chemicals include
Mitsubishi-Kagaku, Croda, Dai-ichi-Kogyo Seiyaku,
Goldschmidt, Sisterna, Weixi Spark, Evonik Industries and
BASF (Hill and Rhode 1999; Cruces et al. 2001;
MarketsandMarkets 2019a; Parker, Khan, and York 1973).
The methods of synthesis of sucrose-based esters was the
subject of a concise review in 2001 (Polat and Linhardt
2001) and surveys of enzymatic approaches have followed
(Shi, Li, and Chu 2011; Gumel et al. 2011). In the present
article we delineate both industrial and laboratory-based
CONTACT Ping Lan ping.lan@jnu.edu.cn Institute for Advanced and Applied Chemical Synthesis, Jinan University, Zhuhai, Guangdong 510632, China.
ß2020 Taylor & Francis Group, LLC
CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION
https://doi.org/10.1080/10408398.2020.1798346
processes for the formation of the title esters that have
emerged in the intervening period. In addition, a commen-
tary on the emulsifying properties as well as the antimicro-
bial, antitumor and insecticidal activities of these important
esters is provided. Structure-property profiles arising from
an examination of these follows.
Chemical synthesis
Many simple esters are prepared by esterification under
Fischer-type conditions from the relevant acid and alcohol
but sucrose esters are not readily formed by such direct
means (Parker, Khan, and Mufti 1976). This is because
sucrose undergoes glycosidic bond cleavage under the neces-
sary conditions (viz.atpH2–3 and 70–80 C) and so pro-
ducing a mixture of glucose and fructose (which is called
inverted or invert sugar) (Soares et al. 2019). Accordingly,
the industrial production of sucrose esters normally involves
the transesterification of fatty acid esters with sucrose and
so circumventing the need to employ strongly acidic condi-
tions (Parker, Khan, and Mufti 1976).
Establishing a single-step, inexpensive and regioselective
chemical synthesis of sucrose fatty acid esters is particularly
challenging given there are eight distinct hydroxyl groups
associated the parent carbohydrate (Queneau et al. 2008).
The per-ester sucrose octaacetate was prepared as early as
1880 by Herzfeld (1880) and in 1939 Cantor (1939) patented
a method for forming sucrose fatty acid esters from starch
factory by-products and simultaneously claimed that such
products could be used as emulsifying agents or fats. Of
course, there are many possible esters (255 in fact) available
by combining, through esterification, any given acid with
sucrose, including 8 mono-esters, 28 di-esters, 56 tri-esters
and so on (Weiss et al. 1971). Given the mono-esters of
sucrose are the most desirable as emulsifiers because of their
generally more appropriate HLB values (see below) (Polat
and Linhardt 2001), methods for the selective production of
these have been the focus of considerable attention. Of the
eight distinct hydroxyl groups embodied within sucrose it
has been established, unsurprisingly perhaps, that acylation
occurs preferentially at the primary ones and with some
selectivity being observed between these, viz. at the 6-OH
(glucose unit), then at the 60-OH (fructose unit) and, finally,
at the 10-OH (fructose unit) positions (Haines 1976).
However, the difference in reactivity of these centers is not
such that mono-esterification is readily achieved and a
detailed evaluation of the composition of sucrose esters
from various commercial sources (Table 1) emphasizes this
point (Cruces et al. 2001). In this study a large variation in
mono- and di-ester ratios was observed, a feature that
reflects the differing synthetic protocols used to make these
compounds as well as the potential for equilibration between
certain of them. Related studies are notable for their use of
quantitative GC and HPLC techniques to achieve the separ-
ation of the component esters and the often effective detec-
tion of these using evaporative light scattering (ELS) and/or
refractive index techniques (Moh, Tang, and Tan 2000).
Current industrial syntheses
Methods for the large (industrial) scale production of
sucrose esters traditionally involves the transesterification of
sucrose using a suitable triglyceride, a process normally con-
ducted in the presence of a catalyst such as potassium car-
bonate or a potassium soap. N,N-Dimethyformamide (DMF)
is the often used solvent (Parker, Khan, and York 1973) but
given its cost, toxicity and other safety issues, reactions
employing DMSO have also been explored. Under favorable
circumstances, mixtures comprising greater than 50%
sucrose mono-ester can be obtained with the remaining
components being other esters and the starting materials
(Figure 1) (Polat and Linhardt 2001). Challenges remain,
however, since removal of these high-boiling solvents
(153 C for DMF and 189 C for DMSO) (Royal Society of
Chemistry 2019) is a non-trivial matter and compounded by
the relatively low thermal stability of the product esters. The
necessary separation of by-products, so as to raise the
mono-ester component to levels acceptable to the market
(Guti
errez et al. 2018), is problematic and also creates waste
streams and so increasing production costs. Sucrose mono-
esters have also been produced industrially from fatty acid
methyl esters using reversible transesterification process with
attendant removal of co-produced methanol so as to drive
the reaction forward. Under the optimal conditions this
protocol can provide material containing upwards of 70% of
the mono-ester (Polat and Linhardt 2001).
Solvent-free processes have also been developed and used
in industry. So, for example, in 1970, Feuge et al. (1970)
found that the so-called interesterification of a suitable fatty
acid methyl ester with molten sucrose in the presence of
catalytic quantities of soap (usually a potassium soap) at
170–185 C can produce the required mono-esters. However,
this approach has drawbacks since at the required (elevated)
temperatures sucrose only remains a liquid for brief periods
(several minutes) and when reduced pressures are applied to
remove the co-formed methanol then degradation of the
sugar occurs as evidenced by the significant darkening of
the reaction mixture. This impacts on both throughput and
product quality while the need to remove the catalyst adds
further technical difficulties (and attendant financial bur-
dens). Another solvent-free and large-scale process was
developed by Parker, Khan, and York (1973) and wherein
Table 1. Composition of commercial sucrose esters as determined by Plou
and coworkers (Cruces et al. 2001).
Compound Source
Composition (by wt.%)
Sucrose Mono-esters Di-esters
Sucrose caprylate Calbiochem 2 95 3
Sucrose caprate Sigma 5 93 2
Sucrose laurate Fluka 2 95 3
Sucrose laurate L70-C Sisterna 11 50 39
Sucrose laurate L-1695 Mitsubishi-Kagaku 2 77 21
Sucrose laurate L-595 Mitsubishi-Kagaku 0 27 43
Sucrose myristate M-1695 Mitsubishi-Kagaku 1 77 22
Sucrose palmitate P-1670 Mitsubishi-Kagaku 0 64 22
Sucrose palmitate P-1570 Mitsubishi-Kagaku 0 59 29
Sucrose palmitate P-170 Mitsubishi-Kagaku 2 88 10
Sucrose palmitate Sigma 9 65 26
Sucrose stearate S-1670 Mitsubishi-Kagaku 0 54 20
2 Y. TENG ET AL.
fine particles of sucrose are reacted with triglycerides (in the
form of oils such as tallow, palm oil or coconut oil) in the
presence of catalytic amounts of potassium carbonate. In
this way, the reaction can be performed at atmospheric pres-
sure and temperatures of around 125 C. Furthermore, the
reaction can be accelerated by adding emulsifiers (e.g. a
diglyceride). However, under such conditions a mixture of
sucrose esters and glycerides is formed. While attractive in
principle, the challenges (as mentioned above) attending the
solvent-free production of sucrose mono-esters mean that
DMF continues to be employed, as a matter of course, in
many commercial processes.
Laboratory-scale syntheses
Nature and selectivity of acylating agents
Approaches to sucrose esters that avoid traditional and nor-
mally ineffective (see above) Fischer esterification
approaches (Figure 2a) abound but it is clear that pure
mono-ester formation cannot be achieved by simply control-
ling the fatty acid ester stoichiometry in transesterification
reactions (Figure 2b). Furthermore, acyl group migration
can occur during the course of such reactions and/or during
isolation and thus introducing additional components into
the product mixture (Queneau, Fitremann, and Trombotto
2004). Sucrose ester syntheses using acyl chlorides (Figure
2c) have been studied with, for example, the esterification of
sucrose by octanoyl chloride at pH 10 shown to provide
mixtures of mono-octanoates, di-octanoates and tri-octa-
noates. By employing 4-(N,N-dimethylamino)pyridine
(DMAP) as an acylation catalyst under dilute conditions,
and by exploiting hydrophobic effects, greatly enhanced pro-
portions of mono-octanoates can be obtained (Th
evenet
et al. 1997). However, the need to strictly control the water
content of the reaction medium while using such protocols
as well as the high cost of catalysts such as DMAP mean
they are likely to be less attractive in industrial settings
(Kea, Walker, and Kline 1987;Th
evenet et al. 1999).
A range of replacements for acid chlorides as the acylat-
ing agent, including acid anhydrides and enol esters, has
been explored. So, for example, the Plusquellec Group
effected regioselective acylation at the 60-OH group of
sucrose using various 3-acyl-5-methyl-1,3,4-thiadiazole-
2(3H)-thiones (Figure 2d) in conjunction with diazobicyclo-
[2.2.2]octane (DABCO) (as base) at low temperature and
DMF as solvent (Chauvin and Plusquellec 1991).
Intriguingly, the same group found that by using 3-acyl-thia-
zoledine-2-thiones in the presence of NaH then a higher
yielding reaction took place and now at the C2-OH group
of sucrose (Chauvin, Baczko, and Plusquellec 1993). The
Queneau Group completed a detailed study on the distribu-
tion of sucrose mono-acylation products obtained on using
N-decanoylthiazolidinethione (Figure 2d) and various homo-
logues as electrophiles (Molinier et al. 2003). Dipotassium
hydrogenophosphate proved to be an effective base in these
cases and it was concluded that N-acylthiazolidinethiones
are better acylating agents than cyanoethyl-, methyl-
thioethyl- and methyl-esters. In another study, 6-O-acylated
sucrose derivatives were accessed in a highly selective man-
ner through reaction (in DMF) of the parent sugar-derived
dibutylstannylene acetal dimers with fatty acid anhydrides
(Vlahov, Vlahova, and Linhardt 1997; Bazin, Polat, and
Linhardt 1998). Subsequently the same sorts of intermediates
were used to regioselectively produce 6-O-acylsucroses and
6,30-di-O-acylsucroses (Wang, Zhang, and Yang 2007) but
such attractive outcomes are offset by the possibility of
product contamination by toxic tin residues. The three-fold
benzoylation of sucrose using benzoyl chloride in the pres-
ence of pyridine has been shown to occur selectively at the
6-O,1
0-Oand 6-Opositions although various other tri-ben-
zoates and certain tetra-benzoates are also produced (Clode
et al. 1985).
Irreversible transesterification reactions involving vinyl
esters (Figure 2d) provide a unique approach to the forma-
tion of sucrose mono-esters with vinyl acetate having been
used to acetylate sucrose. This reaction was reported to take
place in water under basic conditions at slightly elevated
temperatures although the regioselectivity of the process is
not clear (Smith and Tuschhoff 1957). In 2001, Plou et al.
reported the transesterification of sucrose using vinyl capryl-
ate, laurate, myristate or palmitate under strictly anhydrous
conditions in DMSO with Na
2
HPO
4
serving as the catalyst
(Cruces et al. 2001). By such means, remarkably high yields
Figure 1. The most common methods used for the industrial preparation of sucrose mono-esters (Parker, Khan, and York 1973; Polat and Linhardt 2001).
CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION 3
(86–97%) of product mixtures rich in mono-esters
(90–94 wt.% as determined by HPLC) were realized, an out-
come that compared favorably with industrial processes in
operation at the time. The predominant product of such
reactions was the 2-O-acylated material but the co-produc-
tion of its 3-O-acyl counterpart, arising through acyl group
migration, could not be avoided.
Much research into “solvent-free”transesterification reac-
tions has focused on the “solubility”of sucrose in the prod-
uct ester over the temperature range of 40–140 C with
substrate decomposition only becoming evident above this
upper limit. Notably, the solubility of sucrose in the methyl
esters of various fatty acids was observed to increase from
0.25 to 1.40 g/100 g following addition of 2.5 wt.% sodium
stearate and even more so in presence of the surfactant
S1570 (Zhao et al. 2014).
Selective di-esterification at the 6-Oand 60-Opositions of
sucrose can be achieved using gallic acid as the nucleophile
under Mitsunobu conditions (Potier et al. 1999). In these
cases it is assumed that the surcrose-derived oxyphospho-
nium ion, prepared using PPh
3
and DIAD, undergoes
nucleophilic displacement (and the product esters were
examined for their capacities to serve as antioxidants).
Other Mitsunobu-based approaches have provided 6-O-pal-
mitoylsucrose (47% yield) (Bottle and Jenkins 1984) and the
corresponding 6-O-polyfluoroalkanoates (Abouhilale,
Greiner, and Riess 1991). 6-O-Acyl-30,60-anhydro- and 6-O-
acyl-30,40-anhydro-sucroses have been formed as by-products
during the esterification of unprotected sucrose by related
means (Molinier et al. 2004). These epoxide-containing
compounds can also be formed deliberately by using
Mitsunobu protocols (Guthrie, Jenkins, and Yamasaki 1980).
The esterification of sucrose and certain of its congeners
through coupling with activated sulfonic acid derivatives has
also been the subject of several studies and variations in the
reaction conditions provide complementary outcomes in
terms of regioselectivity (Bazin, Polat, and Linhardt 1998;
Kowalski, Cmoch, and Jarosz 2014; Wuts and Greene 2006;
Buchanen and Cummerson 1972; Teranishi 2002). Thus,
sucrose 2-O-p-toluenesulfonate can be obtained under one
set of conditions, while modest changes to these provides
access to the 6-Oor 60-Oregioisomers (Teranishi 2002).
The effect of bases
As suggested by the outcomes of certain of the reactions
described above, the choice of base employed in sucrose
esterification reactions can have a significant influence on
the yield of such processes. While both NaOH and KOH
can be useful for such purposes, in water and other protic
solvents their use leads to saponification of the desired ester.
As such they are only effective under strictly anhydrous con-
ditions, a requirement that limits their utility in industrial
settings. The milder potassium carbonate is a more suitable
catalytic base with a recent study of its application in the
esterification of sucrose using coconut esters in DMF focus-
ing on quantitating the most effective molar ratio of sucrose
to fatty acids, catalyst concentration, solvent volume, reac-
tion temperature and viscosity (Deshpande et al. 2013).
Sonication has been explored as a means for promoting the
esterification of sucrose and under appropriate conditions
good yields of mixtures of sucrose mono-esters can be
obtained. For example, the (trans)esterification of sucrose in
DMSO at 70 C using ethyl palmitate and K
2
CO
3
was
achieved in 73% yield to give a product mixture containing
92% of a ca. 2.5:1 mixture of the 6-O- and 60-O-acylated
mono-esters (Huang et al. 2010a). Related transesterifica-
tions employing K
2
CO
3
in methanol have been reported
(Vassilev et al. 2016).
Combinations of the acetylating agent N-decanoylthiazoli-
dinethione and various carbonates such as K
2
CO
3
,Li
2
CO
3
and Cs
2
CO
3
or phosphates (e.g.,K
2
HPO
4
) have been trialed
Figure 2. Procedures used for the production of sucrose esters: (a) esterification; (b) transesterification; (c) acyl chloride-based esterification and d) examples of
traditional and modern acylating agents (Chauvin and Plusquellec 1991; Chauvin, Baczko, and Plusquellec 1993; Molinier et al. 2003).
4 Y. TENG ET AL.
at ambient temperatures for effecting the esterification of
sucrose. A 71% yield of the 2-O-acylated mono-ester was
achieved using two equivalents of K
2
HPO
4
while various
mixtures of the 3-O,3
0-O4-O(diester), 2-O,4
0-O,6-Oand
10-O,6
0-Ocongeners were also observed with the precise
distribution being dependant on the base used (Molinier
et al. 2003). Some preference for formation of the 2-O,3-O-,
and 6-O-alkanoyl sucroses was seen. So when, for example,
lithium carbonate was employed selective esterification at
the 2-OH group was observed.
Acyl migration methods and sucrose ester stability
Both inter- and intra-molecular acyl migration protocols,
viz. transesterifications, play a pivotal role in the derivatiza-
tion of carbohydrates including sucrose. NMR techniques
involving
13
C-labeled substrates have been used to study
acyl group migrations within 1b-O-acyl glucuronides (Figure
3) (Akira et al. 1998) and, as might be expected, such migra-
tions most likely involve intramolecular nucleophilic attack
by the adjacent hydroxyl group at the carbonyl moiety and,
thereby, formation of a tetrahedral intermediate that itself
collapses to form the migrated product. Depending upon its
strength, added base can facilitate migration through accel-
eration of one or other of the discrete steps shown in Figure
3and under suitable conditions such acyl migrations can
provide a useful means for obtaining single regioisomeric
forms of carbohydrate mono-esters. Since 6-O-acylated
sucroses and their 10-Oand 60-Ocounterparts are the most
stable of the eight possible mono-esters (Molinier et al.
2003), these can be prepared by treating, for example, the
isomeric 2-O-acylsucroses with a (hindered) organic base
and so effecting O-acyl migration in up to 60% yield. Such
processes have been exploited to prepare both 6-O-octanoyl-
sucrose and 6-O-stearoylsucrose (Baczko et al. 1995). In an
extensive study of the isomerization of 3-O-monolaurate
sucrose acyl under basic conditions, the rate of migration
from the 3- to the 6-position was found to accelerate in the
presence of water both during the aqueous workup and
under the HPLC conditions used for analysis (Molinier et al.
2003). Notably, no significant isomerization of the substrate
occurred when this was treated with 1,8-diazabicy-
clo[5.4.0]undec-7-ene (DBU) in the absence of water.
While acyl migrations from the 2-Oto the 3-Opositions
are reversible, at equilibrium the 3-O-ester is normally
favored (Cruces et al. 2001; Baczko et al. 1995). Migration
from the 3-Oto the 6-Oposition can be observed and a
detailed study involving the use of various acylating agents,
including acid chlorides and alkyl chloroformates, estab-
lished that a range of factors, including steric ones, impact
on mono-ester product distributions (Th
evenet et al. 1999).
If appropriate control of various physical and chemical
parameters is attained then pure mono-esters can often
be generated.
Summary
While various laboratory-scale protocols have been estab-
lished for the reliable and selective production of sucrose
mono-esters, the translation of these into industrial settings
is challenging, not least because solvents such as pyridine
cannot be used in the food industry while acylating agents
such as acyl chlorides and vinyl esters are prohibitively
expensive and/or are environmentally disadvantageous. Such
issues have attracted the recent attention of various aca-
demic groups who acknowledge industrial imperatives and
have thus pursued the use of enzymes to prepare sucrose
esters. The nature and outcomes of such studies are
now discussed.
Enzymatic syntheses
Enzyme-catalyzed syntheses of sucrose esters offer a pathway
to higher purity forms of these products as a result of their
enhanced regioselectivities. Furthermore, these biocatalytic
processes are generally environmentally-friendly ones
because of the mild conditions involved and the nontoxic
nature of the (often aqueous) media involved (Franssen
et al. 2013). To date, however, no commercial sucrose ester
production process appears to exploit this enzyme-based
approach, not least because of the associated costs and the
need for these to be run in batch rather than flow mode
(Satyawali, Vanbroekhoven, and Dejonghe 2017). Both
lipases and proteases can be used for the esterification of
sucrose (Chang and Shaw 2009). The associated processes
have also been employed extensively for the production of
Figure 3. Acyl migration processes observed within the glucuronide framework (Akira et al. 1998).
CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION 5
other sugar esters, including lactose monolaurate (Walsh
et al. 2009). Detailed studies of such transformations, some
outcomes of which are discussed in the following sections,
reveal that the nature of the solvent, the water content of
the medium and the temperature as well as the method of
mixing are often crucial. Such requirements are dictated by
the need to retain/preserve/protect the enzyme active site
(viz. to avoid denaturing of the enzyme).
Lipases
Lipases are a group of esterases that catalyze the hydrolysis
of lipids and such enzymes are comprised of several sub-
classes including phospholipases and acylglycerol lipases
(Schomburg et al. 2017). In the present context, the most
important lipases are, arguably, the triacylglycerol lipases
(EC 3.1.1.3) that selectively hydrolyze insoluble triacylglycer-
ols at the substrate-water interface (BRENDA 2019b). As
such these lipases, especially immobilized forms, have found
a multitude of applications in industry particularly for flavor
and biodiesel production as well as in the treatment of waste
water (Filho, Silva, and Guidini 2019). Various lipases have
also been used for the laboratory-scale preparation of
sucrose esters, including certain commercially available and
immobilized ones such as Lipozyme TL IM (a lipase derived
from the thermophlic fungus Thermomyces lanuginosus, for-
mally Humicola lanuginosa) (Ferrer et al. 2005) and
Novozym 435 (derived from the yeast Candida antarctica B)
(Shao et al. 2018; Ye, Hayes, and Burton 2014).
Generally, when a lipase is hydrated then only small
amounts of water need be present in the reaction medium
so as to ensure its catalytic viability (Goderis et al. 1987).
On the other hand, since lipases function in equilibrium
(Figure 4a), hydrolysis of the product ester can occur even
when anhydrous (organic) solvents are employed (Gumel
et al. 2011). Thus, determining the optimal water content of
the reaction medium is a major consideration in any associ-
ated methodological studies (Chamouleau et al. 2001; Gumel
et al. 2011). Unlike many enzymes that follow
Michaelis–Menten kinetics, lipase acyl-transfer reactions are
thought to proceed through a “bi-bi ping-pong mechanism”
(Figure 4b) with competitive substrate inhibition being
caused by the alcohols used as acyl acceptors (Martinelle
and Hult 1995; Reyes-Duarte et al. 2005).
Solvent effects
Lipases remain viable at low concentrations in a range of
organic solvents including n-hexane, DMSO, methanol,
xylene and cyclohexane (Salihu and Alam 2015). So, for
example, Novozym 435 has been deployed in the prepar-
ation of long-chain long fatty acid esters by treating sucrose
with the relevant acylating agent in a mixture of DMSO and
2-methyl-2-butanol as so to produce sucrose palmitate
(Reyes-Duarte et al. 2005). While the use of DMSO facili-
tates dissolution of the sugar, it can impact negatively on
the enzyme activity although this can be overcome by using
higher concentrations of the acyl donor and/or by employ-
ing, for example, vinyl palmitate as a reactant and thereby
rendering esterification irreversible. This last tactic signifi-
cantly broadens the applicability of such enzymes across a
range of reaction and substrate types.
The capacities of ionic liquids (ILs) to solubilize both
polar and non-polar species provides unique possibilities for
simultaneously dissolving both sucrose and fatty acid esters
and thereby facilitating reaction between them. Given their
green “credentials”(Otomo et al. 2009; Anastas and Warner
1998), thermal stabilities, salt-like properties in the liquid
state (and that often occurs at room temperature) (Welton
1999), good specific conductivities and negligible vapor pres-
sures, ILs have been exploited in a multitude of settings
(Johnson 2007). They are noted for their abilities to dissolve
biomass components (Singh 2019) and have been employed
as solvents in reactions involving lipases (Itoh 2017) and so
exploited in the preparation 6-Oand 6a-O-linoleyl-a-D-mal-
tose (Fischer et al. 2013).
Figure 4. (a) Lipase esterification of carbohydrates and hydrolysis of carbohydrate esters (Neta, Teixeira, and Rodrigues 2015); and (b) the “bi-bi ping-pong”transes-
terification mechanism (Reyes-Duarte et al. 2005).
6 Y. TENG ET AL.
There have been various reports of the enzyme-catalyzed
synthesis of sugar fatty acid esters in ionic liquids (Yang
and Huang 2012). However, only a few of these have
focused on sucrose ester formation, probably because of the
low solubility of sucrose in conventional ILs and/or the
enzyme denaturing properties of such solvents (Shi, Li, and
Chu 2011). As part of efforts to circumvent these difficulties,
the Sheldon group (Liu et al. 2005) established that the solu-
bility of sucrose in [BMIm][dca] is 195 g/L at 25C and
282 g/L at 60 C. Furthermore, they revealed that this IL can
be used in the Novozym 435-catalyzed acylation of sucrose
by dodecanoic acid at 55 C. In related work, Huang et al.
studied the enzymatic preparation of 6-O-lauroylsucrose by
reaction of sucrose with lauric acid vinyl ester and con-
cluded that by deploying Lipozyme TL IM in [BMIM]BF
4
the target ester could be obtained in 50% yield (Huang et al.
2010b). Shao et al. (2018) reported a synthesis of the same
sucrose mono-ester in a 1.5:1 v/v mixture of
[3CIM(EO)][NTf
2
] and 2-methyl-2-butanol and so affording
the product in 66% yield, a pleasing outcome attributed to
the capacity of this IL to maintain the high activity of the
lipase and to enhance the solubilities of the substrates.
Supercritical CO
2
has also been exploited as a solvent in
various lipase-catalyzed biotransformations (Knez 2018). So,
for example, an immobilized lipase from Candida antarctica
B(EC 3.1.1.3) was used in supercritical CO
2
at 10 MPa to
produce sucrose palmitate and sucrose laurate (Habulin,
Sabeder, and Knez 2008). The addition of molecular sieves
to that reaction affording sucrose laurate from equimolar
amounts of the fatty acid and sucrose at 60 C resulted in a
74% conversion. The non-toxic and non-flammable nature
of CO
2
means these types of reactions are considered amen-
able to the industrial preparation of food additives.
Yields and selectivity
Recent reports have revealed that the regioselective produc-
tion of sucrose esters can be effected in 40–90% yield using
the lipases derived from Bacillus thermoproteolyticus,
Candida antarctica,T. lanuginosus,Bacillus pseudofirmus
AL-89 and Bacillus subtilis. However, in order to realize
these outcomes acylating agents such as vinyl esters and
anhydrides are required. Interestingly, essentially quantita-
tive yields of a product sucrose ester were achieved using
2,2,2-trifluoroethyl butyrate as the acyl donor in conjunction
with the Bacillus protease Bioenzyme 240. When pyridine
was used as the solvent this combination of reactants pro-
duced 10-O-butyryl sucrose (Patil, Rethwisch, and Dordick
1991). Lipases were less effective. Significantly, lipases
derived from Rhizomucor miehei have been used to effect
the high-yielding formation of sugar mono- and di-esters
with simple carboxylic acids serving as the acyl donors
(Dang, Obiri, and Hayes 2005; Ye, Pyo, and Hayes 2010).
The selective acylation at the 6-Oand 60-Opositions of
sucrose is often observed when lipases are employed for this
purpose (Shi, Li, and Chu 2011) although other less-com-
mon enzymes allow for alternative outcomes. Plou’s group
reported the preparation of 6-O-lauroylsucrose and 6-O-pal-
mitoylsucrose (Ferrer et al. 1999) through acylation of
sucrose using mixed-solvent combinations and lipases
derived from various species but most notably an immobi-
lized form obtained from Humicola lanuginosa Candida
rugosa lipase (CRL) has also been used in transesterification
studies for the formation of sucrose-6-O-acetate with various
reaction parameters, including temperature, concentration
and pH, being examined and so leading to the identification
of an effective two-phase system comprising 2-butanol and
Tris-HCl buffer at an initial pH of 8.60 and a temperature
of 47 C. Under such conditions the target mono-acetate
was obtained in 57% yield (Zhong et al. 2013).
Reaction parameters
The Hayes’group has reported detailed studies on the use
of the immobilized lipase derived from Rhizomucor miehei
(viz. Lipozyme IM ex. Novozymes) for preparing sucrose
esters and by such means a 9:1 mixture of mono- and di-
esters was obtained in 80–93% combined yield when oleic
acid was employed as the acyl donor (Dang, Obiri, and
Hayes 2005). Notably, only small quantities of solvent (tert-
butanol) were required during the early stages of the
reaction and after a 25% conversion had been realized the
product sucrose ester served as the reaction medium. The
same enzyme and protocols were used for the esterification
of sucrose and fructose with oleic acid. The reaction took
6 days and led to a liquid phase consisting of an 11.5:1 mix-
ture of mono- and di-esters in 88% combined yield (Ye,
Pyo, and Hayes 2010). Similarly high yields were realized
using acetone or methyl ethyl ketone (butanone) instead of
tert-butanol or, alternatively, using carefully defined mix-
tures of oleic acid and fructose or sucrose.
Both Rhizomucor miehei and Candida Antarctica-derived
lipases have been used in esterifications under conditions
involving high-speed homogenization and high-intensity
ultrasonication of the reaction mixtures. These conditions
were found to be effective in reducing the size of sucrose
particles in a solvent-free synthesis of sucrose oleate (Ye,
Hayes, and Burton 2014). It has also been observed that
pre-incubation of C. Antarctica lipase B (CALB) in oleic
acid at 60 C for 24 h enhances the initial rate of enzymatic
esterification. Moreover, the synthesis of sucrose esters using
either acrylic resin or chitosan immobilized CALB in con-
junction with oleic acid, sodium sulfate and ethanol, deliv-
ered product yields of 56 and 55%, respectively (Neta
et al. 2012).
A lipase derived from T. lanuginosus and its immobilized
form, Lipozyme TL IM, have also been used to produce 6-
O-lauryl sucrose from vinyl laurate. Thus, Ferrer et al.
(2002b) prepared a silica-granulated lipase (particle size
around 0.3–1 mm) obtained from T. lanuginosus, and this so
immobilized enzyme allowed for the synthesis of sucrose
mono-laurate in >95% yield when a mixture 4:1 v/v tert-
amyl alcohol and DMSO was deployed as the solvent system
at 40 C and sucrose added to the reaction mixture in por-
tions. The capacity to recycle this enzyme is highlighted by
its ability to continue to effect this reaction in 80% yield
over 20 cycles, each of which lasts ca. 6 h (Ferrer et al.
2005). The regioselective synthesis of 6-O-palmitoylsucrose
CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION 7
catalyzed by Lipozyme TL IM in a continuous flow micro-
reactor has been reported (Du and Luo 2012) and involves
using silicone tubing (inner diameter 2.0 mm) with a Y-
shaped junction at the start point that is packed with silica
spheres (0.3–0.9 mm) carrying surface-adsorbed enzyme. To
carry out the reaction, solutions of sucrose (in 2-methyl-2-
butanol and DMSO) and vinyl palmitate (in 2-methyl-2-
butanol) were injected into the junction for mixing then
flushed through the microreactor. At 40 C (and using a
flow rate of 20.8 lL/min that resulted in a residency time of
0.5 h), a high conversion (95%) of sucrose into the corre-
sponding 6-O-acyl mono-ester was realized. This outcome is
attributed to the favorable surface area-to-volume ratio of
the Lipozyme TL IM presenting on the silica particles.
Proteases
While most reports on the enzymatic preparation of sucrose
esters involve the use of lipases, deploying proteases
(Rawlings et al. 2018) for the same purpose has also been
explored in the ongoing efforts to achieve ever higher regio-
selectivities and yields within useful timeframes. An attract-
ive feature of proteases is their relative stabilities and good
activities when used in conjunction with organic solvents
such as DMF and DMSO (Plou et al. 2002). In general, pro-
teases selectively acylate at the 10-Oposition of sucrose in
such solvents as well as in pyridine (Riva et al. 1988). Thus,
an examination of the effectiveness of subtilisin conducted
by Riva et al. (1988) established that this enzyme is catalytic-
ally active in anhydrous DMF and allows for the production
of 10-O-monobutyrylsucrose in 85% yield and with 90%
selectivity. Using a stabilized, insoluble and commercially
available polymer of substilisin called ChiroCLEC-BL
Linhardt et al. were able to produce a range of 10-O-acyl
sucrose esters that were accompanied by minor amounts of
the corresponding 10,6-di-O-acylated (di-ester) derivatives
(Polat, Bazin, and Linhardt 1997). The most effective reac-
tion conditions employed dry pyridine as the solvent and
vinyl esters as the acyl donors. More recently, Protex 6 L, a
commercially available and alkaline protease derived from
Bacillus licheniformis, was used to synthesize sucrose mono-
laurate (Wang et al. 2012). In this process, vinyl laurate dis-
solved in a 15:1:4 v/v/v mixture of tert-amyl alcohol/DMSO/
water was treated with fine particles of sucrose (0.2 mm).
By such means 98% of the sucrose was converted, regiose-
lectively, into 10-O-lauroylsucrose after 9 h and so establish-
ing that Protex 6 L is superior to many commonly used
enzymes including the immobilized lipase Novozym 435.
The alkaline soda lakes of Ethiopia have proven to be
interesting sources of proteases including one derived from
Bacillus pseudofirmus AL-89 that functions within the pH
range 7–10 in the presence of 7.5% v/v water (Pedersen
et al. 2003). Under such conditions vinlyl laurate can be
used to effect sucrose esterification at the 2-position rather
than its 10or 6-counterparts. Another 2-O-selective acetyl-
ation of sucrose is achieved using the neutral metallopro-
tease thermolysin (E.C. 3.4.24.27) in DMSO. This catalytic
process relies, as confirmed by EDTA binding and other
studies, on the presence of zinc in the active site (Pedersen
et al. 2002; Lie, Meyer, and Pedersen 2014).
Liao’s group has reported regioselective acetylation at the
40-Oposition of sucrose using a purified serine protease
derived from Serratia sp. SYBC H and thus providing
sucrose-40-Omono-acetate in more than 90% yield (Li et al.
2011a). In contrast, when a crude alkaline protease obtained
from the same source was used then exhaustive and high
yielding peracetylation of sucrose was observed (Li
et al. 2011b).
Other enzymes
A 2016 study focused on the preparation of sucrose 6-O
acetate employed Aspergillus oryzae fructosyltransferase
(E.C. 2.4.1.9 or, as recommended by BRENDA, inulosucrase)
(BRENDA 2019a) that was originally isolated from a sample
of root soil associated with the growth of sugarcane (Wei
et al. 2016). This enzyme, which has been shown to transfer
a fructosyl unit from one sucrose residue to another (Wei
et al. 2014), was deployed in various IL/buffer combinations
with sucrose and glucose 6-Oacetate as substrates. The best
medium for the reaction proved to be a 1:4 v/v
[Dmim][PF
6
]/phosphate buffer system and under optimal
conditions 88% conversion of glucose 6-Oacetate was
observed and the product sucrose 6-Oacetate obtained in
77% yield. In 2017, a novel, chemoenzymatic route to a new
class of sucrose esters was reported (Possiel, B€
auerle, and
Seibel 2017). The enzyme used in this case was Bacillus sub-
tilis levansucrase (EC 2.4.1.10, a member of the glycoside
hydrolases family of 68 enzymes) that is known to hydrolyze
sucrose as well as effect transfer of the fructosyl moiety of
sucrose (Ortiz-Soto et al. 2017). By such means, the glucose
residue of sucrose was substituted for various D-glucuronic
or D-galacturonic acid ester residues to form the corre-
sponding b-D-fructofuranosyl-(2,1)-a-D-glucuronic or galac-
turonic acid esters.
Table 2. Commercial enzymes used in the preparation of sucrose esters.
Enzyme Other Names
Lipase (Thermomyces lanuginosus, previously Humicola lanuginosa) (Ferrer
et al. 2005)
Lipozyme
V
R
TL IM (Shao et al. 2018)
Lipase (Candida Antarctic B) Novozym 435
V
R
(Ye, Hayes, and Burton 2014)
Lipase (Rhizomucor miehei) Lipozyme IM
V
R
(Dang, Obiri, and Hayes 2005; Ye, Pyo, and Hayes 2010)
Lipase (Candida rugosa) CRL (de Maria et al. 2006)
Serine protease subtilisin (Bacillus licheniformis) ChiroCLEC-BL (Polat, Bazin, and Linhardt 1997); Protex 6L (Wang et al. 2012);
Subtilisin A, Subtilopeptidase A, Novozymes Alcalase
V
R
(Rawlings et al.
2018); Subtilisin Carlsberg (Delange and Smith1968)
8 Y. TENG ET AL.
Summary
Certain of the commercially available enzymes used for the
preparation of sucrose esters are listed in Table 2 and their
selectivities are summarized in Figure 5. Further, and as out-
lined above and emphasized in Table 3, enzymes can pro-
vide greener and more selective methods for obtaining
sucrose esters, including ones that are often inaccessible by
other means. Nevertheless, much remains to be done within
this promising area of sucrose mono-ester synthesis, both
for the purposes of making “customized”and essentially
pure forms of such systems in “boutique”quantities as well
as in the production of such systems at commercial scales
for the food industry. The use of, inter alia, protein
engineering, directed evolution and gene shuffling techni-
ques for the production of dedicated enzymes capable of
meeting industry demands for superior sucrose-ester pro-
duction processes will certainly be a focus of ongoing efforts
in this area.
Sucrose esters as emulsifiers
Sucrose esters are of great interest as surfactants. For more
than fifty years the food industry has been developing meth-
ods for preparing various sucrose esters with a “tunable”
range of surface activities (Tucker and Martin 1958; Roshdy,
Horst, and Herbert 1967). As a result, a large number of
Figure 5. The regioselectivities exhibited by various enzymes available for the formation of sucrose esters and certain derivatives.
Table 3. Brief comparison of various methods available for the synthesis of sucrose esters.
Synthesis Method Advantages Disadvantages
chemical preparation methods in general catalyst cost is usually low;
some economical processes have been
industrialized
are generally less selective and so yield a mixture
of esters;
complicated product purification;
generation of waste streams
transesterification in solvents (typically DMF) providing >70% of monoester;
preferred industrially
solvents are often toxic and difficult to remove
solvent-free inexpensive raw material and catalyst cost;
can be industrialized
forms a mixture of esters;
degradation of sucrose leads to darkening
with acid chlorides enhanced proportions of mono-esters strict control of water content required;
high catalyst cost;
unfavorable in industry
with fatty acid vinyl esters (also applicable
with enzymes)
the irreversible reaction affords high yields and
high mono-ester content;
often preferred in lab settings
high cost of acylation reagent and hence
unfavorable in industry
with other acylation agents (e.g., acid anhydrides
and enol esters)
can achieve high selectivity complicated reaction procedures makes it
unfavorable in industry
under Mitsunobu conditions preparation of functional esters (e.g., gallic acid
ester) in lab
complicated reaction procedures make it
unfavorable in industry
enzymatic preparation methods in general high selectivity;
green processes and purer products
high catalyst cost;
industrialization is challenging
in organic solvents facilitates dissolution of sugar organic solvents can deactivate enzymes
in ionic liquids can dissolve both substrates and thus facilitate
the reaction
low solubility of sucrose in conventional ionic
liquids;
enzyme denaturing
in supercritical CO
2
solvent is non-toxic and non-flammable high production cost
reduced solvent and solvent-free system avoids massive use of solvents small sucrose particles are needed;
homogenization or ultrasonication is often
needed to promote reaction
CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION 9
sucrose esters is now available commercially for satisfying
diverse needs in a wide range of areas. Various parameters
have been used to characterize and calibrate their properties
as surfactants (Table 4) and so assisting with their commer-
cial success (Griffin 1949; Griffin 1954; Ren and Lamsal
2017; Pearce and Kinsella 1978; McClements 2015).
The emulsifying capacity of surfactants can be very
clearly determined/demonstrated by measuring the particle/
droplet sizes and their distributions associated with the
emulsions formed using them. In order to examine droplet
size, various devices, including laser diffraction particle-size
analyzers, can be employed and a plot of continuous size
distribution is then generated by the software packages nor-
mally associated with such instruments. In general, a smaller
mean value and narrow standard deviation of the distribu-
tion signifies a better emulsifying capacity (Walstra 2002).
McClements (2015) suggested that droplet size will influence
a range of properties of the emulsions including stability,
optical behaviors, rheology and even sensory attributes (Ren
and Lamsal 2017; Pearce and Kinsella 1978).
HLB values and their utility
Sucrose esters have unique surface-active properties arising
from their amphiphilic nature that itself derives from the
presence, within the molecular framework, of the hydro-
philic hydroxyl groups associated with the sucrose moiety
and hydrophobic characteristics associated with the fatty
acyl side-chain. The hydrophilicity or lipophilicity of a sur-
factant is often measured by the so-called hydrophilic-lipo-
philic balance (HLB) that ranges in value from 0
(completely lipophilic/hydrophobic) to 20 (completely
hydrophilic/lipophobic) (Griffin 1949; Griffin 1954). In the
case of sucrose esters, a wide range of HLB values can be
achieved by controlling the type of associated fatty acids and
the degree of esterification of the carbohydrate framework
(Plou et al. 2002). As would be expected, longer acyl chains
or higher degrees of esterification will increase the
hydrophobicity and thereby decrease the HLB value. In
practice, the HLB values of commercial sucrose esters range
between 1 and 16 (Mitsubishi Chemicals 2019; Sisterna
2019a). It is also possible to blend sucrose esters with other
surface active compounds (often glycerides) to meet differ-
ent needs (Gupta, James, and Smith 1983). As noted by Ye
and Hayes (2014), sucrose esters with HLB values 5 are
used in chocolates to form water-in-oil emulsions while
those with intermediate HLB values (8–10) are best used in,
for example, chewing gum for their more balanced lipophi-
licity and hydrophilicity. Those esters with HLB values 11
are widely used in ice cream and cake batter to form oil-in-
water (an opposed to water-in-oil) emulsions. The type of
fatty acid residue involved also impacts of the utility of the
sucrose esters. For example, when the HLB value of the sur-
factant is between 11 and 16, as seen in sucrose esters with
12, 14, 16, 18 and 18:1 carbon-containing acyl groups (viz.
in laurate, myristate, palmitate, stearate and oleate esters
derivatives), these are used as detergents, in ice cream, in
milk beverages, in cake batter, and in sauces or dressings,
respectively (Ye and Hayes 2014). A great deal of informa-
tion about the surface-active properties and applications of
sucrose esters is provided in the scientific literature (Otomo
et al. 2009; Ye and Hayes 2014) and/or on manufacturers’
websites (Mitsubishi Chemicals 2019; Sisterna 2019a).
Various new studies relating to the HLB values of sucrose
have been reported. So, for example, Jiang et al. (2019)
investigated the competitive interfacial adsorption of com-
mercial emulsifiers such as Mitsubishi’s lipophilic sucrose
stearate (S-370, HLB ¼3) and its more hydrophilic counter-
part (S-1670, HLB ¼16). They found that, overall, the for-
mer was superior in producing well-textured frozen aerated
emulsions. These same authors claimed that lipophilic emul-
sifiers accelerated crystallization of fat, promoted interfacial
heterogeneous nucleation as well as partial coalescence of fat
droplets, enabled strong aeration activity, and allowed a
short melting starting time. Sucrose ester S-1170 (HLB ¼
11) was also added (in up to 6% w/w) into a high amylose
starch-based wood adhesive so as to improve bonding/shear
Table 4. Parameters commonly used to characterize the emulsifying effects of surfactants.
Parameter and formula Definitions of variables
Hydrophilic-lipophilic balance (HLB) value (Zhang et al. 2014):
HLB ¼20 Mh
M
M
h
:molar mass of the hydrophilic moiety.
M:molar mass of the surfactant molecule.
Foamability (Zhang et al. 2014):
FA ¼HTH0
H0100%
H
0
:height of surfactant solution before foam formation.
H
T
:total height of foam and solution measured immediately after foam formation.
Foaming stability (Zhang et al. 2014):
FS ¼Ht
Hi100%
H
i
:foam height measured immediately after foam formation.
H
t
:foam height after the sample was rested for some time.
Emulsifying ability (Zhang et al. 2014):
EA ¼H1
H0100%
H
0
:height of surfactant solution and an oil phase (e.g., equal volume of soybean oil)
H
1
:height of the emulsion layer measured immediately after homogenization.
Emulsion stability (Zhang et al. 2014):
ES ¼H2
H1100%
H
1
:height of the emulsion layer measured immediately after homogenization.
H
2
:height of the emulsion layer after the emulsion was rested for some time.
Emulsion stability index (Ren and Lamsal 2017; Pearce and Kinsella 1978):
ESI ¼A0t
A0At100%
A
0
:initial absorbance obtained immediately after homogenization and dilution.
A
t
:absorbance obtained after the test sample was rested for certain time.
t: time that the test sample was rested (e.g., 20 min).
Size distribution (McClements 2015):
Sn¼Ð1
0xnFx
ðÞ
dx Pi¼1nixn
i
xab ¼Sa
Sb
1=ðabÞ
cn¼SnSnþ2
S2
nþ1
1
1=2
S
n
: the nth moment of the distribution.
x
ab
: the mean particle size.
a,b: integers (usually between 0 and 6).
c
n
: relative standard deviation weighted with the nth power of x.
n: the nth moment of the distribution.
n
i
: the number of droplets in a size-class.
10 Y. TENG ET AL.
strength (in both dry and wet states), mobility, storage and
thermal stability as well as rheological and degradation
resistant properties. At the micro-level, the addition of this
sucrose ester was found to hinder the aggregation of latex
particles as well as their dispersion (Zia-Ud-Din et al. 2017;
Zia-Ud-Din et al. 2019). Sucrose esters were also added to
tobacco shred so as to improve their humectant and mois-
ture resistant properties. Similarly, the hydrophobic portion
of the sucrose ester S-5 (HLB ¼5), as supplied by the
Zhejiang Synose Tech Co., Ltd., was shown to play an
important role in reducing the interaction of tobacco shred
with water (Lin et al. 2020). Likewise, sucrose esters,
together with other small molecular emulsifiers, were found
to reduce the degradation of starch in food products like
pancake mixtures (Yamashita et al. 2020). This reduction
was attributed, in the main, to emulsifier-starch complex
formation and so reducing the leaching of starch molecules
from product granules. The degree of such complexation
was, in turn, influenced by the HLB values of the emulsi-
fiers involved.
The development of synthetic methods (in particular
enzymatic ones) has enabled the preparation of high purity
sucrose mono-esters and these have allowed for in-depth
comparative studies of their surface-active properties (Ferrer
et al. 2002a). So, Zhang et al. (2014) have reported that a
longer acyl chain (C8–12) results in a reduction of HLB
(14.5 to 13.1) and CMC (0.78–0.45 mM) values while the
associated
cCMC
values increase (32.36–34.54 m/Nm). By
comparing fatty acid sugar mono-esters incorporating
C12–18-containing acyl chains, it was found that those
involving the longer ones decrease the CMC values while
for those embodying the same length of acyl chain the order
of CMC values was: sucrose >maltose >leucrose >
maltotriose (Ferrer et al. 2002a). All in all, most studies of
the surface properties of sucrose esters reveal that they are
good surfactants with a wide range of practical applications.
Foaming properties
Much confectionery, including ice cream, mousses and
marshmallow, use food emulsifiers to provide a satisfying
texture, attractive appearance and long shelf-lives. As such,
the so-called foamability of these emulsifiers as well as the
stability of the derived foams (foam stability) are of vital
importance (Hutzler et al. 2011). Surfactants stabilize the
foams by preventing bubbles from coalescing (Belhaij and
Al-Mahdy 2015) so foamability, which is defined as the sur-
factants’capacity to form foams, and foam stability (a metric
derived by determining variations in foam height or volume
as a function of time), are important metrics used to define
the foaming properties of food emulsifiers (Husband
et al. 1998).
At the early stage, Husband and coworkers demonstrated
that a 4:1 molar ratio of sucrose mono- and di-esters can
display superior foaming properties as a result of interac-
tions between these constituents (Husband et al. 1998). It is
also widely recognized that the stability of foams derived
from sucrose octaacetate decreases on standing (Petkova
et al. 2017). Tual et al. (2006) have suggested that the desta-
bilization of fat droplet interfacial layers in dairy products
can be caused by the presence of sucrose esters meaning
that optimal concentrations of these must be established so
as to produce the most stable and high-quality dairy foams.
Furthermore, when the concentration of the sucrose ester is
too low to support foam formation then adding small
amounts (often just 0.050 wt.%) of b-lactoglobulin can
retrieve matters (Garofalakis and Murray 2001). Although
aqueous foams are more common than non-aqueous ones,
more research on the latter has been reported due to their
great potential (Fameau and Saint-Jalmes 2017). For
example, the edible emulsifiers made from sucrose esters
and lecithin contribute to the formation of stable oil foams
involving high air volume fractions and thus showing inter-
esting rheological and thermoresponsive properties likely to
be of value in generating food products possessing novel
textures (Patel 2017).
Emulsifying capacity
Sucrose esters are expected to provide emulsifiers suitable
for deployment in various food products and cosmetics, not
least because of their broad range of HLB values, their non-
toxic nature and their degradation to readily digestible
sucrose and fatty acids. As such, several methodologies and
metrics have been developed so as to quantitate their emul-
sifying capacities (Otomo et al. 2009). For example,
Ariyaprakai and coworkers have reported that sucrose esters
could be employed as a promising replacement for Tweens
in coconut milk emulsions since such substitutions provide
more thermally stable systems (Ariyaprakai, Limpachoti, and
Pradipasena 2013). This group also reported that edible oil-
in-water emulsions derived from sucrose esters are particu-
larly stable toward freezing then thawing (Ariyaprakai and
Tananuwong 2015). Furthermore, Zhao, Chen, and Wu
(2018) demonstrated that the addition of carefully selected
cryogelling polysaccharides such as alginate can enhance the
stability of the associated emulsions toward freeze-thaw
cycles. Similarly, mixtures of polyglycerol monostearate
(PGE) and sucrose esters have proven to be useful in the
preparation of flavor oil emulsions (Ariyaprakai 2016).
Other research has revealed that sub-micron-sized emulsions
can be formed from sucrose esters via a so-called spontan-
eous emulsification process instead of employing higher-
energy homogenization techniques (Ariyaprakai, Hu, and
Tran 2019) and that, under simulated gastrointestinal condi-
tions, sucrose ester-derived emulsions undergo coalescence
while Tween80-based ones do not (Verkempinck
et al. 2018).
Biological activities
While sucrose esters are considered to be safe for humans, a
multitude of studies have reported their inhibitory effects on
microbes, tumor cells and viruses as well as revealing their
insecticidal potential. Such properties are now discussed.
CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION 11
Antimicrobial activity
Since sucrose esters have been widely used in food products,
their antimicrobial activities (including antifungal and anti-
bacterial effects) have been also been studied extensively as
highlighted by the data presented in Table 5. Most early
research in this area used commercially-derived sucrose
esters but in recent years studies have been focused on more
novel and enzymatically-derived systems (Ferrer et al. 2005).
It has been known for sometime that detergent mole-
cules, such as polyoxyethyleneglycol, can bind to bacterial
membranes and so destroying them (Le Maire, Champeil,
and Møller 2000), and it is very likely that sucrose esters
exert their antibacterial effects by the same basic mechanism.
Indeed, as revealed by Shao et al. (2018), the antimicrobial
activity (particularly against Gram-positive bacteria) of
sucrose monolaurate is initiated through disruption of the
integrity of the bacterial cell membrane. This triggers col-
lapse of the cytoplasmic membrane, loss/leakage of intracel-
lular enzymes and the release of K
þ
from the cytosol,
disruption of the subcellular localization of proteins and,
thereby, bacterial inactivation.
Thanks to their antimicrobial properties, sucrose esters
are considered to have a promising future as non-toxic food
preservatives while also possessing unique emulsifying and/
or foaming properties (Habulin,
Sabeder, and Knez 2008).
Yang et al. (2003) suggested that the use of sucrose mono-
esters derived from lauric, myristic and palmitic acids in
salad dressing will also inhibit the growth of microorganisms
involved in spoilage. In fact, sucrose esters even show
inhibitory effects on the growth of spores, prompting
Shearer et al. (2000) to suggest using sucrose laurate for
food applications where high-temperature processing is
undesirable. Another interesting use of sucrose esters is in
oral-care products like toothpaste. It has been reported that
6-O-lauroylsucrose completely inhibits the growth of the
oral bacterium Streptococcus sobrinus and so suggesting that
such compounds could be included in oral-hygiene products
in order to disrupt plaque formation and thereby preventing
(or at least reducing) dental caries (Devulapalle et al. 2004).
Given their increasingly broad deployment, the possible
emergence of microorganisms resistant to sucrose esters has
been investigated. As Sugimoto et al. (1998) discovered,
while some commercial sucrose mono-esters inhibit the
development of Bacillus cereus spores as well as the vegeta-
tive growth of cells, the germinated spores and growing cells
can release esterases that promote ester degradation and so
aiding their capacity to regenerate (viz. become resistant).
Antitumor activities
In 1971, Kato et al. showed that the water-soluble sucrose
esters incorporating laurate, myristate, palmitate and linole-
ate residues exhibit strong in vitro antitumor activity against
Ehrlich ascites tumors in mice. Subsequently, the Nishikawa
group reported a series of studies on the chemical and bio-
chemical properties of synthetic and commercially available
carbohydrate esters including sucrose esters. The group first
revealed that sucrose mono-esters of myristic acid
(Nishikawa et al. 1976a) as well as elaidic and oleic acids
(Nishikawa et al. 1976b) exerted marked inhibitory activities
against Ehrlich ascites carcinoma in mice. Subsequently,
they found that sucrose mono-esters of palmitic, stearic,
hydnocarpic and ricinoleic acids exerted antitumor effects
against this cancer as well (Nishikawa et al. 1977a). These
studies have been extended to commercial sucrose esters as
well as other tumor cell lines and so revealing that mono-
ester-rich systems exhibit pronounced antitumor effects
(Nishikawa et al. 1977b; Ikekawa et al. 1979). A consider-
ation of the possible mechanisms of actions of these esters
as cytotoxic agents suggested that they might not just act as
detergents (and so disrupting tumor cell membranes) or as
prodrugs for the associated fatty acids (Nishikawa et al.
1976a) but also have inherent antitumor properties them-
selves (Nishikawa et al. 1977a). Such a possibility is sup-
ported by the observation that as the HLB value of the
sucrose monoester increased the associated ID
50
value
decreased (Ikekawa et al. 1979).
Interestingly, plant-derived sucrose esters can also exhibit
antitumor activities. Thus, in 2017, Fang et al. reported the
isolation of eight isovaleryl sucrose esters (named ainslosides
A–H) from Ainsliaea yunnanensis Franch, and discovered
that congener B (Figure 6a) exerted notable cytotoxic effects
against the A549 (lung adenocarcinoma) cell line with an
IC
50
of 3.3 lM. This compound was found to arrest the cell
cycle at the G
0
/G
1
phase and induce cell apoptosis with the
latter effect arising from a decrease in mitochondrial mem-
brane potential and an attendant growth in the levels of
growth of reactive oxygen species. In 2018, Petrova et al.
synthesized a library of sugar esters with C3–5 unsaturated
fatty acyl chains and found that 6-O-methacryloyl sucrose as
well as 10,2,3,30,4,40,60-hepta-O-acetyl-6-O-methacryloyl
sucrose (Figure 6b) were the most active against a range of
food contaminating and clinically notable pathogens (MIC:
0.24–1.40 lM). The later ester also showed good antifungal
activity (MIC: 0.28–1.10 lM). Synthetic, non-fatty-acid
sucrose esters possessing antitumor activities have also been
identified. For example, Bai (2009) prepared a unique
sucrose selenite (Figure 6c) showing promise in treating can-
cers. This compound has a selenium content of 17.4% which
is significantly higher than that of conventional selenium-
containing nutrients and anticancer drugs (ca. 1.2%). It
exhibited excellent antimutagenic bioactivity as evidenced by
an inhibition rate of 97.4% when applied in a standard assay
at a loading of 500 lg/dish.
Sucrose fatty acids esters have also been used in drug
delivery systems (Abdel-Mageed et al. 2012; Guan, Chen,
and Zhong 2019). For example, Guan, Chen, and Zhong
(2019) recently reported that a sucrose fatty acid ester pur-
chased from the Tokyo Chemical Industry Co. in Japan
(Product No. S0112) could be used to nanoencapsulate caf-
feic acid phenethyl ester (CAPE), a natural product possess-
ing anticancer activities but low water solubility. Such
encapsulation is expected to enhance the capacity to deploy
CAPE in the treatment of certain colon and breast cancers.
Of course, the possible synergistic effects associated with the
12 Y. TENG ET AL.
Table 5. Summary of the literature reporting the antimicrobial activities of sucrose fatty esters.
Sucrose ester Active Against Comment Ref.
6-O-lauroylsucrose L. monocytogenes,B. subtilis,S.
aureus, and E. coli.
Indicates significant antimicrobial
activity against these bacteria,
particularly Gram-positive bacteria.
Shao et al. 2018
Sucrose monolaurate
(6-O-lauroylsucrose, from Sigma-
Aldrich Co.)
Gram-positive bacteria Exerted bacteriostatic and bactericidal
effects against these bacteria.
Park et al. 2018
Physakengoses
(natural sucrose esters isolated
from Physalis alkekengi
var. franchetii)
Staphylococcus aureus,Bacillus subtilis,
Pseudomonas aeruginosa, and
Escherichia coli.
Five out of seven natural sucrose
esters isolated displayed potent
antibacterial activity, and long
chain fatty acid esters attached to
sucrose were essential for
this activity.
Zhang et al. 2017
Sucrose monocaprate
(home-made)
Bacillus cereus,Bacillus subtilis,
Staphylococcus aureus,Escherichia
coli, and Salmonella typhimurium.
Displayed the strongest antibacterial
activity against these bacteria,
particularly Gram-positive bacteria.
Zhao et al. 2015
Octa-O-acetylsucrose 17 Microorganisms:
Gram-positive and Gram-negative
bacteria, yeasts, and fungi
Inhibited the growth of fungi
Penicillium sp., Rhizopus sp. and
Fusarium moniliforme, and yeasts
Candida albicans. Did not inhibit
Gram-positive and
negative bacteria.
Petkova et al. 2017
Sucrose esters with C8, C10, C12, C14
and C16 fatty acids
(Mitsubishi-Kagaku Foods
Co., Japan)
Bacillus species: B. cereus,B. subtilis,
B. megaterium, and B. coagulans
Sucrose esters displayed bactericidal
effects on these species at pH 6.0,
but only showed an antibacterial
effect on B. coagulans at pH 8.0
(better at 37 C than 50 C).
Nakayama et al. 2015
Sucrose monolaurate
(from Sisterna, the Netherlands)
Gram-positive and Gram-
negative bacteria
Most effective against the growth of
Gram-positive bacteria (inhibited
Listeria and greatly inhibited
S. suis).
Wagh et al. 2012
Sucrose monolaurate
(from AppliChem Inc.,
Darmstadt, Germany)
Escherichia coli O157:H7 The efficacy of chlorine (from NaOCl)
sanitization was significantly
improved by sucrose monolaurate
which enables inactivation or
removal of the microorganism.
Xiao et al. 2011
Commercial sucrose ester
(sucrose palmitate, P-1670, from
Mitsubishi-Kagaku Food Co., 80%
mono ester), or enzymatically
synthesized sucrose laurate (mono
and diesters)
Gram-positive bacterium B. cereus
(ATCC 11778)
At 9.375 mg/mL, commercial and
enzymatically synthesized sucrose
laurate inhibited 99.8% and 94.0%
of the growth of B. cereus after
52 h.
Mono-esters inhibit B. cereus to
higher extent than di-esters.
Habulin,
Sabeder, and Knez 2008
6-O-lauroylsucrose (2 mg/mL)
6,10-di-O-lauroylsucrose (1 mg/mL)
6,60-di-O-lauroylsucrose
(0.25 mg/mL)
Bacillus sp.,Pseudomonas fluorescens,
Staphylococcus aureus,Escherichia
coli, and Pichia jadinii
Inhibited the growth of Bacillus sp.,E.
coli and L. plantarum. But the
antimicrobial activity of these
diesters was negligible as a result
of their limited solubility.
Ferrer et al. 2005
6-O-lauroylsucrose Streptococcus sobrinus In media supplemented with
2 mg/mL of the sucrose ester,
bacterial growth was
not observed.
Devulapalle et al. 2004
Sucrose monoesters of lauric,
myristic, palmitic, and stearic acids.
Zygosaccharomyces bailii, and
Lactobacillus fructivoran
The growth of Z. bailii was
significantly inhibited by 1%
sucrose monoesters of lauric,
myristic and palmitic acid in salad
dressing, but the inhibition of L.
fructivorans lacks practical value.
Husband et al. 1998
Sucrose laurates, palmitate, and
stearates (Mitsubishi Chemical Co.,
N.Y., U.S.)
Spores of Bacillus sp., Clostridium
sporogenes PA3679, and
Alicyclobacillus sp.
In terms of sporeformer inhibition,
sucrose laurates and palmitate
were more effective
than stearates.
Shearer et al. 2000
Sucrose palmitate (P-1570 and P-
1670)
Sucrose stearate (S-1570 and S-
1670)
(Mitsubishi-Kagaku Foods Co.)
L. monocytogenes,Bacillus cereus
(both cells and spores),
Lactobacillus plantarum, and
Stuphylococcus aureus
Improved the antimicrobial activity of
nisin (an antibacterial peptide
used as a food preservative)
against these strains. Inhibition of
Gram-negative bacteria was
not observed.
Thomas et al. 1998
Sucrose monolaurate (SE12), sucrose
monopalmitate (SE16), and sucrose
Bacillus cereus Inhibit the germination of spores,
with the effectiveness of
laurate >palmitate >stearate, and
Sugimoto et al. 1998
(continued)
CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION 13
simultaneous deployment of two proven cytotoxic agents in
such settings is worthy of investigation.
Insecticidal activities
A less studied aspect of sucrose esters properties concerns
their insecticidal effects. In 1994, field and green house stud-
ies of Nicotiana gossei Domin plants led to the identification
of an isolate, containing 2,3-di-O-acyl-10-O-acetylsucrose and
2,3-di-O-acyl-10,60-di-O-acetylsucrose, that proved toxic to
sweet potato whiteflies. The side-chains associated these esters
were predominantly derived from 5-methylhexanoic and 5-
methylheptanoic acids (Figure 6d) (Severson et al. 1994).
Subsequent reports described the insecticidal activity of cer-
tain synthetic sugar esters, including sucrose-based ones,
against a range of insects including Bemisia argentifolii (Liu,
Stansly, and Chortyk 1996; Chortyk, Pomonis, and Johnson
1996). Synthetically-derived sucrose esters containing C
6
–C
12
aliphatic acid residues (Youngs 1958) and especially dihepta-
noyl, dioctanoyl and dinonanoyl-containing ones, were shown
to be active against whiteflies and aphids (Chortyk 2003)and
field tests of these (to protect various crops) were undertaken.
The prospect of using Nicotiana species for producing sugar
esters as “biorational”insecticides has also been pursued
(Jackson et al. 1998).
McKenzie and Puterka (2004) have studied the insecti-
cidal activities of sucrose octanoate and in so doing found
that nymphal and adult Diaphorina citri (Asian citrus psylla)
as well as mites were both controlled to considerable effect
(>90%) by sucrose octanoate, albeit at rather high concen-
trations (8000 ppm). Given that sucrose octanoate is essen-
tially nontoxic to many beneficial insects, this ester may
prove to be a useful (selective) pesticide in commercial set-
tings. Song et al. (2006), who prepared sucrose octanoate by
transesterification of sucrose with ethyl octanoate under
reduced pressure, have also evaluated the insecticidal activity
of this compound. They reported that the contact toxicity of
sucrose octanoate to first-instar larvae of Lymantria dispar
was 72.5% after 36 h, and the insect reduction rate, after
5 days, of Aphis glycines was above 80% at application rates
of 4 and 8 mg/mL. Considering the emulsifying properties
and other advantages of sucrose esters (such as their bio-
degradability as well as lack of toxicity toward higher ani-
mals and crops), they represent promising leads for the
development of commercial insecticides.
Puterka et al. (2003) studied the structure-activity profiles
of various sugar esters in an effort to determine the origins
of their insecticidal properties and claimed that changing
the fatty acid and sugar residues in such systems resulted in
unpredictable levels of insecticidal activity. Notably, their
HLB values did not correlate with activity. So, for example,
they observed that monoester-rich sucrose octanoate had
higher activities than other esters embodying acyl chains of
similar length (C6–12) and was toxic to a broader range of
arthropod species. Interestingly, a comparison of the insecti-
cidal activities of sugar esters and soaps led to the conclu-
sion that more than one mechanism-of-action might be
involved with one of these being suffocation caused by
mechanical occlusions of body openings and another being
desiccation of insect cuticles.
Structure-property profiles
In general, the overall surfactant and emulsifying properties
of sugar esters are profoundly influenced by both the length
of the associated fatty acid chain (viz. the hydrophobic tail)
and the nature of the sugar residue (viz. the hydrophilic
head) (Zhang et al. 2015). In the case of sucrose esters,
Table 5. Continued
monostearate (SE18)
(Mitsubishi-Kagaku Foods Co.)
the vegetative growth of cells. But
the germinated spores and
growing cells can release esterases
to decompose these esters,
causing loss of
antimicrobial activity.
Sucrose monocaprate, and
Sucrose monolaurate
Listeria monocytogenes, and
Staphylococcus aureus
The monocaprate (400 lg/mL) did
not inhibit growth, while the
monolaurate exhibited an
inhibitory or lethal effect and this
can be enhanced by EDTA.
Monk, Beuchat, and Hathcox 1996
Sucrose monolaurate Streptococcus mutans NCTC 10449
(an oral bacterium)
Reduced acid production from sugar.
This is due to altering of cell
membrane permeability causing
loss of important metabolites.
Iwami, Schachtele, and Yamada 1995
Six sucrose esters with fatty acid
composition of ca. 70% stearic
acid and 30% palmitic acid. (DKS
International Inc., Tokoyo, Japan)
Aspergillus,Penicillium,
Cladosporium, and Alternaria.
Antimycotic activity was detected
against listed molds. The least
substituted sucrose ester was the
most active, and this inhibitory
activity was not influenced by
variations in pH.
Marshall and Bullerman 1986
Sucrose caprate, caprate, laurate,
myristate and palmitate (Ryoto Co.
Ltd., Tokyo, Japan.)
Vibrio parahaemolyticus The minimum concentrations for
inhibition by sucrose caprylate and
caprate were 40 and 100 lg/mL,
respectively. The rest of the esters
studied were ineffective at
100 lg/mL.
Beuchat 1980
14 Y. TENG ET AL.
precisely how their properties vary as a function of the
length of the fatty acid residue (structure-property profiles)
remains unclear. Zhang et al. (2015) have prepared and
characterized three sucrose medium-chain fatty acid (octa-
noate, decanoate and laurate) mono-esters and found that
increasing hydrophobic chain length enhances the emulsify-
ing potencies of medium-chain fatty acid mono-esters.
However, sucrose mono- and di-esters bearing longer (>12
carbons) chain fatty acids have yet to be properly evaluated
in this regard. As well as the acyl chain length, it can be
expected that increasing the degree of acylation/esterification
leads to a higher hydrophobicity and so decreasing surface
activity. A more important issue is the associated decline in
water solubility, a property that limits applications in the
food industry (Ferrer et al. 2002a). In principle, the degree
of unsaturation of the acyl chain should have limited influ-
ence on the surface properties, as it does not significantly
alter the molar mass of the hydrophilic moiety and, hence,
the HLB. Although the practical applications of sucrose
esters in the food industry are guided, at least in a rudimen-
tary sense, by their hydrophilic-lipophilic balance (HLB) val-
ues (Ye and Hayes 2014), the development of detailed
structure-property profiles are wanting. Once established
these would be expected to aid in the selection of the most
relevant ones for any given practical application(s).
In terms of the bioactivities of sucrose esters, it seems
that mono-esters rather than higher order ones play pivotal
roles, and the influence of the acyl chain length may also be
Figure 6. Selected sucrose esters showing biological activities: a) ainsloside B (Fang et al. 2017); b) sucrose esters of some unsaturated fatty acids (Petrova et al.
2018); c) sucrose selenite (Bai 2009); and d) the natural pesticides 2,3-di-O-acyl-10-O-acetylsucrose and 2,3-di-O-acyl-10,60-di-O-acetylsucrose (the acid residues of
which are mostly derived from 5-methylhexanoic and 5-methylheptanoic acids) (Severson et al. 1994).
CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION 15
involved. Thus, it has been shown that mono-esters are sig-
nificant antibacterial entities with the corresponding di- and
tri-esters displaying less notable activities possibly because of
their low(er) aqueous solubility. The length of the fatty acid
residue has a notable influence on activity
(C12 >C10 >C8), almost certainly a result of its influence
on the HLB that is involved in the inhibitory effect (Zhang
et al. 2014). In terms of the antitumor activity, the
Nishikawa group has concluded that mono-esters are most
active and that there might often be an inverse correlation
between HLB and the ID
50
values (Nishikawa et al. 1977b;
Ikekawa et al. 1979). Unsaturation within the fatty acyl
chains (Nishikawa et al. 1976a,1976b) has little impact on
activity unless a Michael acceptor is involved (e.g., Petrova
et al. 2018). In terms of insecticidal activity, the impact of
the fatty acid residue is unpredictable although a high
mono-ester content sucrose octanoate exhibits high toxicity
to a broad ranges of species (Puterka et al. 2003). Clearly,
more research is required so as to fully reveal the mecha-
nisms-of-action of such compounds and thereby establishing
guidelines for their practical applications.
In our recent work on homologous series of glucose, mal-
tose, lactose and raffinose esters (Liang et al. 2018a,2018b;
Ma et al. 2018;Lietal.2019) we established that in order to
maintain good foaming properties, fatty acid side chains of
10 or 12 carbons in length are required regardless of the
nature of the sugar residue involved. So, while the incorpor-
ation of longer fatty acid side-chains results in better emulsi-
fying potencies for glucose and raffinose esters, medium
length ones are more effective when bonded to their maltose
and lactose counterparts. Intriguingly, in the case of lactose
esters, the longer the alkyl side chain the greater their cyto-
toxicities. However, determining analogous and unequivocal
structure-property profiles for sucrose esters is complicated
by the mixed nature of most commercially available materials
that can often include seven or more types of fatty acid resi-
dues. Clearly further work in this important area is required.
Conclusion
In recent years, there has been a growing interest in the use
of sucrose esters as emulsifiers because of their excellent
properties, especially as these can be exploited in the food
industry. An associated body of knowledge focused on their
preparation has accumulated as a result and attendant,
detailed studies of their emulsifying properties and various
bioactivities have emerged. While rather conventional chem-
ical methods dominate the industrial production of such sys-
tems, a more recent but largely academic focus has been on
the enzymatic preparation of sucrose esters. There are dis-
tinct advantages associated with such approaches given that
they are generally greener and less energy-demanding proc-
esses but the likely cost of the enzyme required in applying
such protocols in industrial settings remains a challenge.
The antimicrobial, antitumor and insecticidal activities of
sucrose esters are important emerging areas of study, espe-
cially considering that such compounds are also likely to be
useful as food additives, drug carriers and/or emulsifiers.
Clearly, this is an evolving field of science where exciting
new discoveries are being made.
Funding
The authors thank the Program for Guangdong Pearl River
Introducing Innovative and Entrepreneurial Teams (grant
2017ZT07C571), the Program for Guangdong Yang Fan Introducing
Innovative and Entrepreneurial Teams (grant 2016YT03H132), the
Science and Technology Planning Project of Guangdong Province
(grant 2016A010105010) as well as the National Natural Science
Foundation of China (grant 21801094 and grant 31701525)
for funding.
ORCID
Yinglai Teng http://orcid.org/0000-0002-6260-8498
Scott G. Stewart http://orcid.org/0000-0002-7537-247X
Yao-Wen Hai http://orcid.org/0000-0003-3850-3239
Xuan Li http://orcid.org/0000-0001-8201-7751
Martin G. Banwell http://orcid.org/0000-0002-0582-475X
Ping Lan http://orcid.org/0000-0002-9285-3259
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