Sucrose diesters

Triglycerides Diglycerides Monoglycerides Sucrose monoesters Sucrose diesters... 

Sucrose Monoester Sucrose Diester Triglycerides Diglycerides Monoglycerides... 

Table 1 Transition temperatures TO of the and 6,6 - aliphatic sucrose diesters.

Enzymatic acylation reactions offer considerable promise in the synthesis of specific ester derivatives of sucrose. For example, reaction of sucrose with an activated alkyl ester in /V, /V- dim ethyl form am i de in the presence of subtilisin gave 1 -0-butyrylsucrose, which on further treatment with an activated fatty acid ester in acetone in the presence of Hpase C. viscosum produced the 1, 6-diester derivative (71,72). 

Parrish (1977) reviewed the research and development of lactose ester-type surfactants carried out by Scholnick and his colleagues (Scholnick et al. 1974, 1975 Scholnick and Linfield 1977). Their initial attempts to form lactose esters followed the same transesterification procedures that had been used with sucrose (a fatty acid methyl ester in N,N-dimethylformamide with potassium carbonate as the catalyst). Their successful approach was the reaction of lactose in N-methyl-2-pyrrolidone as the solvent with fatty acid chlorides, resulting in yields of 88 to 95% for esters of lauric, myristic, palmitic, stearic, oleic, and tallow fatty acids. The principal product was the monoester, which is important for detergent use, since diesters and higher esters of lactose are not water soluble. 

Once bearing some substituents, the decrease of polarity of the sucrose derivatives makes them soluble in less-polar solvents, such as acetone or tert-butanol, in which some lipases are able to catalyze esterifications. Unlike proteases, which necessitate most often the use of an activated acyl donor (such as vinyl or trifluoroethyl esters), lipases are active with simple esters and even the parent carboxylic acids in the presence of a water scavenger. The selectivity of the lipase-catalyzed second esterification is specific for OH-6 allowing the synthesis of mixed T,6 -diesters.123,124 For some lipases, a chain-length dependence on the regiochemistry was observed.125 Selectively substituted monoesters were thus prepared and studied for their solution and thermotropic behavior.126,127 Combinations of enzyme-mediated and purely chemical esterifications led to a series of specifically substituted sucrose fatty acid diesters with variations in the chain length, the level of saturation, and the position on the sugar backbone. This allowed the impact of structural variations on thermotropic properties to be demonstrated (compare Section III.l).128... 

V. Molinier, J. Fitremann, A. Bouchu, and Y. Queneau, Sucrose esterification under Mitsu-nobu conditions Evidence for the formation of 6-0-acyl-3, 6 -anhydrosucrose besides mono and diesters of fatty acids, Tetrahedron Asymmetry, 15 (2004) 1753-1762. 

P. Potier, A. Bouchu, G. Descotes, and Y. Queneau, Lipase-catalysed selective synthesis of sucrose mixed diesters, Synthesis (2001) 458-462. 

OMe was found by Fujino et al.(11) to be 22000 33000 times sweeter than sucrose. It is not exactly known whether the sweettasting isomer has the L-L(or S-R) or the L-D(or S-S) configuration because of ready racemization. From the examination of its projection formula, it could be predicted that the L-L(or S-R) isomer (42), in which aminomalonic acid diester takes an L(or R)-configuration, would be sweet. This prediction agreed with that reported in the literature (14). 

Glycerides, glucosides, saccharides, sorbitan derivatives, Tweens and Spans, etc. also belong to the class of nonionic surfactants. Mono- and diesters of fatty acids and multiatomic alcohols are oil soluble surfactants with low solubility in water. Sulfoesterification of these compounds followed by subsequent neutralization allows one to obtain water soluble surfactants. Many representatives of this group, such as sucrose esters, are non-toxic, tasteless and odorless, which makes them attractive for use in the pharmaceutical, food and perfume industries. 

As can be seen, several additional hydroxyl groups are available for esterification. Thus, a variety of economically attractive sugar esters with a wide range of HLB may be prepared on a synthetic or enzymatic way. This very mild sucrose acylates are useful as edible emulsifiers and food-grade cleaners. When used in breadmaking, sucrose monoesters and diesters improve the... 

The monoesters of glycerol and the diesters of sucrose not only have higher antimicrobial activity than tlieir corresponding free fatty acids, but also compared favorably in activity with commonly used antiseptics such as parabens, sorbic acid, and dehydroacetic acid (see Tables IV and V). 

Definition Mixture of sucrose esters of stearic acid consists mainly of the diester... 

CAS 25915-57-5 EINECS/ELINCS 247-345-5 Definition Diester of lauric acid and sucrose Empirical CseHeeOis Properties Nonionic... 

Glyceryl stearate lactate Polyglyceryl-10 stearate Sucrose fatty acid esters aerating agent, beet sugar processing Propylene glycol mono- and diesters of fats and fatty acids... 

Sucrose chelates in DMSO react selectively with allyl halide and sodium bromoacetate to produce monoethers in high yields. Sucrose chelates in DMF solution react selectively with acid chlorides, cuihydrides and esters to produce sucrose monoesters or, in some cases, diesters as well. The yields and selectivities of the partial esterification of sucrose via chelates is higher than with other methods. The yield range of the acid derivatives studied are shown in Table XI. 

Under these conditions, the formation of higher esters of sucrose is favoured so that, even in the presence of an excess of sucrose, the product will contain 10% or more of the diester. In practice this rarely is a disadvantage. Other solvents (dimethyl-sulphoxide, pyridine, N-acyl piperidine, etc.) cuid catalysts can be used, but the separation and purification of the sucrose ester still is costly. 

Rhone-Poulenc manufactures sucroglycerides by the Sugar Research Foundation process which involves the use of dimethylformamide as a solvent, which means that the product must be purified in order to meet the low requirements for dimethylformamide. This product has a high content in mono- and diester of sucrose, a low content in sucrose and low in soap. It is used mainly in the animal food field in reconstituted milk for calf feeding because of its tensioactive properties. Other applications in human markets have been found. 

In our work we used the Lemieux modification (14) of the Hass procedure to produce sucrose esters of pure fatty acids (capryllic to arachidic, including oleic acid). We used silica gel chromatography to isolate and purify the monoester and, in some cases, the diester fractions. The pure esters were characterized by saponification number and sucrose content. They had no effect on the production of CO2 in a yeast-flour ferment. 

The data in Table VII show that sucrose monopalmi-tate (G14) was very active in overcoming the volumedepressing effect of soy flour in bread, whereas the diester fraction behaved passively. The control... 

We are not in a position to make any precise statements about regioisomerism within the mono- and diester classifications but information can be gleaned from a somewhat speculative interpretation of the nmr (nuclear magnetic resonance) spectra of these products. Work in this area still is in progress and, for example, our tentative conclusion regarding sucrose phthalate is that substitution has occurred at the 6,6 and 4 positions in sucrose. 

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