Lactose fatty acid ester

FIG. 3 Synthesis of lactose fatty acid esters by esterification of crude lactose acetals. 

Physical studies on glycosides have included the X-ray diffraction analysis of methyl a-D-galactopyranosides and methyl p-D-glucopyranosides with fatty acid esters at C-6 which showed bilayer structures with zig-zag alkyl chains. The conformational behaviour of several non-ionisable lactose analogues have been examined by NMR and molecular mechanics methods, and the energy profile of methyl p-D-arabinofuranoside as a function of ring conformations has been determined by gas phase computations. ... 

An anti-tumour formulation containing sodium palmitoleate, lactose, fatty acid sucrose esters, and magnesium stearate has been patented and is claimed to be effective against Ehrlich ascites tumours in mice (Toyo Jozo Co Ltd, 1984). 

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. 

The lactose esters and their ethyoxylated (prepared by treatment with ethylene oxide) derivatives possessed surfactant properties comparable to those shown by analogous sucrose derivatives. The best detergency properties were shown by the lower fatty acid monoesters of lactose. The comparable lactitol esters were slightly better detergents than the lactose esters no improvement was brought about in either case by the ethylene oxide adducts. The esters of both lactose and lactitol are readily biodegradable. 

Many lactose esters, including those of long-chain fatty acids, have been prepared by using the respective acid anhydride in either alkali or pyridine, and the respective acid chloride in pyridine. A mixture of lactose and phenyl isocyanate in pyridine gives an octaphenylurethan derivative of lactose. The yellow a and anomers of lactose octakis-[p-(p-nitrophenylazo)benzoate] were prepared for chromatographic studies. ... 

Previously, it was reported that the chemical shift of the proton atoms of the C-12 of the fatty acid methyl ester can be found at 3.503 ppm (50). In the HMBC-NMR spectrum, there is a cross peak between this proton of C-12 and the carbon atom with a chemical shift of 95.23 ppm. This is a tertiary carbon atom. The discrimination between quaternary and tertiary C signals has been performed by using an attached proton test (APT) pulse sequence, one each second. The cross peak refers to the three-bond coupling of the H-12 protons with the anomeric center C-1 of lactose. The H-data of C-1 were found with the one-bond coupling constant, which is 150 MHz. With a COSY-NMR spectrum and its corresponding HMBC spectrum, the H and C NMR values of C-2, C-3, could be determined. 

Cottonseed (Gossypium) oil Gelatin Hydrolyzed oat flour Japan (Rhus succedanea) wax Konjac flour Lactic acid esters of mono- and diglycerides of fatty acids Lactitol Lactose Lard Malt extract... 

Figure 7.10 The structures of lactose and lactitol mono-ester surfactants. The asterisks denote alternative locations for the fatty acid substitution.

They are obtained, among other methods, by transesterification of fatty acid methyl esters (14 0, 16 0, 18 0 and/or 18 1, double bond position 9) with sucrose and lactose. The resultant mono- and diesters are odorless and tasteless. Depending on their structure, they cover an HLBrange of 7-13, and are used in stabilization of o/w emulsions, or in stabilization of some instant dehydrated and powdered foods. 

Lactitol and lactose monoesters esters have been prepared by Drummond and Wells [25] with the add ehloride fatty acid derivatives of Cg ig... 

Mono/Diglyceridlactylat Lactose Lactose, Milchzucker Lactylic Esters of Fatty Acids Stearoyl-milchsaure... 

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