Emulsifiers sucrose esters

Sucrose Esters. These newer emulsifiers, approved for direct addition in the United States in 1983 (35), ate formed when sucrose is combined with various fatty acids and the resulting emulsion is dehydrated. These additives are odorless and tasteless, and can withstand the retort process. They are used in products when standards of identity do not preclude their use, such as baked goods, baking mixes, dairy product analogues, fto2en dairy desserts and mixes, and whipped milk products (39). High price has limited use in the United States, but these compounds ate used extensively in Japan as emulsifiers in baked goods (40). 

One advantage of sucrose esters is that they can be made with a wider range of HLB values than other emulsifiers (Figure 3). Chemically, the families of emulsifiers shown in Figure 3 are all esters. As an emulsifier... 

The transesterification of sucrose has been performed with a fatty acid ester of a volatile alcohol in the presence of an alkaline catalyst in a dipolar, aprotic solvent.142 The reaction of sucrose (293 mmoles) with methyl dodecanoate (293 mmoles) in A/,N-dimethylformamide in the presence of sodium methoxide in a pressure bomb for 8 h at 130° gave, after solvent extraction and crystallization, sucrose mono(dodecanoate) (m.p. 72-80° [a]D+52°) in 50% yield.142 Commercialization of these sucrose esters has so far been limited, in part because of the use of expensive solvents, and, in part, because solvent remaining in the product makes it unsuitable for use as a food emulsifier. In view of this situation, methods have been developed in which the use of toxic and expensive solvents has been avoided. 

Emulsifier 473 Sucrose esters of fatty acids 20 83rd mtg 884, p 16, 1997... 

Low-molecular-weight surfactants ( emulsifiers ) are important ingredients in food products. The types of surfactants most commonly studied in food colloids research are phospholipids (lecithin), mono/diglycerides (particularly glycerol monostearate), polysorbates (Tweens), sorbitan monostearate or monooleate (Spans), and sucrose esters. These small lipid-based amphiphiles can typically lower the interfacial tension to a greater extent than the macromolecular amphiphiles such as proteins and certain gums (Bos and van Vliet, 2001). 

Emulsifiers. The chemical structures of emulsifiers, or surfactants, enable these materials to reduce the surface tension at the interface of two immiscible surfaces, thus allowing the surfaces to mix and form an emulsion. An emulsifier consists of a polar group, which is attracted to aqueous substances, and a hydrocarbon chain, which is attracted to lipids. Emulsifiers include mono- and diglycerides, lecithin, propylene glycol esters, luctylated esters, sorbttan and sorbitol esters, polysorbate.x, and sucrose esters. 

The Alkylglycosides (AGs) and Sucrose esters of fatty acids (SEFAs) are families of nonionic glycosurfactants that have been used for their ability to gently extract membrane proteins with a minimal loss of functionality. These compounds can be synthesized and purified economically, with a worldwide production of thousands of tons per year. Chemically, AGs and SEFAs are a group of uncharged amphipathic compounds that consist of an aliphatic hydrocarbon chain attached to a sugar moiety. Certain AGs and SEFAs such as dodecanoyl sucrose have enjoyed widespread use as food-grade emulsifiers and in cosmetic preparations. 

Most studies of the properties of fatty acid sucrose esters relate to their applications as emulsifiers, and are often conducted on mixtures of regioisomers and various levels of substitution. It is clear that the chain length and the number of chains have the largest influence on the surfactant properties 150>373>378 389... 

The use of surfactants in the food industry has been known for centuries. Naturally occurring surfactants such as lecithin from egg yolk or soybean and various proteins from milk are used for the preparation of many food products, such as mayonnaise, salad creams, dressing, and desserts. Polar lipids such as monoglycerides have been introduced as emulsifiers for food products. More recently, synthetic surfactants such as sorbitan esters (Spans) and their ethoxylates (Tweens), sucrose esters, have been used in food emulsions. It should be mentioned that the structures of many food emulsions is complex, and in... 

Sucrose Esters. Sucrose has eight free hydroxyl groups, which are potential sites for esterification to fatty acids. Compounds containing six or more fatty acids per sucrose molecule have been proposed for use as noncaloric fat substitutes under the name Olestra this material acts like a triglyceride fat and has no surfactant properties. Compounds containing one to three fatty acid esters, on the other hand, do act as emulsifiers and are approved for food use in that capacity. They are manufactured by the following steps ... 

Nakamura, S., Using Sucrose Ester as Food Emulsifiers, INFORM 8 866-874 (1997). 

Crodesta. [Croda Inc. Croda Surf. Ltd.] Sucrose esters dispersant, emulsifier, wetting agent, solubilizer, thickener, suspending agent, detergent in cosmetics, toiletries, pharmaceuticals. 

Grilloten. [RITA] Sucrose esters emulsifier, solubilizer. 

Ryoto Sugar Ester. [Mitsubishi Kasei] Sucrose esters emulsifier, softener, conditioner, aerating agent for foods. 

Sucrose esters are non-ionic surface-active materials which could be utilized as emulsifiers and fat replacers.They are synthesized by esterification linking lipophilic fatty acids to the hydrophilic sucrose. Especially the three primary OH groups of sucrose are more easily substituted through fatty acids compared to the secondary ones, thus leading preferably to mono-, di- and tri-esters. These lower-substituted sucrose esters are well suited for application as food emulsifiers especially in dressings and sauces, confectionery, icings and bakery fillings. Cosmetics are another important field of application. 

CAS 26446-38-8 EINECS/ELINCS 247-706-7 Synonyms p-D-Fructofuranosyl-a-D-glucopyranoside monohexadecanoate a-D-Glucopyranoside, p-D-frutofuranosyl, monohexadecanoate Palmitic sucrose ester Saccharose palmitate Sucrose monopalmitate Sucrose palmitic acid ester Definition Monoester of palmitic acid and sucrose Empirical C28HS2O12 Properties M.w. 580.71 nonionic Uses O/w and w/o emulsifier, softener, conditioner, texturizer, and aerating agent in foods protective fruit coatings emulsifier, solubilizer, stabilizer, tablet lubricant, excipient, diluent for pharmaceuticals emulsifier, surfactant, solvent in cosmetics poiymerization emulsifier for food-pkg. film... 

E473 Sucrose esters of fatty acids Emulsifier Compound of fatty acids and cane sugar... 

Sucrose esters of fatty acids having 12 or more carbon atoms display surface active properties. Most of them are odourless and tasteless (or slightly bitter) allowing them to find applications both in food and personal care products [17]. Sucroesters were approved and freely permitted in Japan for use as food additives in 1959 for both their emulsifying ability and their heat stability. In addition, they are well known to protect food proteins from thermal denaturation and inhibit the growth of Escherichia coli and other bacteria. 

The net effect of this questionable attitude thrust upon FDA was that sucrose esters went into commercial production in Japan rather than in the land of their discovery. In Japan they go into cake mixes as emulsifying agents, and so far they have hurt no one. The process of digestion splits the sucrose ester into fatty acid and invert sugar, compounds that are normally present in the body. More recently I have seen reports that the French are using sucrose esters in animal feeds. The results of experiments synthesizing sucrose esters from acid anhydrides, to be reported later in this symposium, are, naturally, of great interest to me. 

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