Alkyl glucosides

SCHEME 1. Acid-zeolite catalyzed formation of alkyl glucosides by Fischer glucosylation and by transacetalation of butyl glucosides. 

M. A. Camblor, A. Corma, S. Iborra, S. Miquel, J. Primo, and S. Valencia, Beta zelite as a catalyst for the preparation of alkyl glucoside surfactants The role of crystal size and hydrophobicity, J. Catal., 172 (1997) 76-84. 

Scheme 5.51 Method for preparation of 2-deoxy-2-C-alkylated glucosides.

G. Legler and E. Bieberich, Isolation of cytosolic P-glucosidase from calf liver and characterization of its active site with alkyl glucosides and basic glycosyl derivatives, Arch. Biochem. Biophys., 260 (1988) 427 136. 

Acylations of carbohydrate derivatives such as alkyl glucosides and galactosides have also been successfully performed in ionic liquids [63]. Similarly, the flavonoid glycosides naringin and rutin were acylated with vinyl butyrate in ionic liquid media in the presence of a number of lipases, e.g., CaLB (Novozym 435), immobilized TIL, and RmL [119]. The products are of interest for application as strong antioxidants in hydrophobic media. 

Fleury, Brissaud and Lhoste [12] also prepared alkyl glucoside esters, using the nitrating mixture described above, composed of nitric acid, acetic anhydride and acetic acid ... 

IFP dispersant additives IFP dispersant additives IFP dispersant additives IFP dispersant additives IFP dispersant additives Polymeric surfactants Alkylarylsulfonates Alkyl glucosides TBAB, a QAS TPAB, a QAS... 

The industrial pro cess is b ased on the Fischer synthesis and commercial development work started some 25 years ago. Once a route using coconut-based alcohols had been established, full-scale plants became viable and alcohol blends are now used to control hydrophobicity of the molecules produced. Thus, products based on C8 alcohols are water soluble and those based on C18 are virtually insoluble. The critical micelle concentration (CMC) values of pure alkyl glucosides and CulCu alkyl polyglucoside (APG) are comparable with those of a typical non-ionic surfactant and decrease with increasing alkyl chain length. 

Glucose 1 mol + fatty alcohol 3-10 mol —> mono alkyl glucoside + water (continually removed)... 

Table 5.11 Examples of commercial poly alkyl glucosides ...

Two new phenylpropanoid glucosides and an alkyl glucoside from the fruits of I. vemm were isolated and their chemical structures were elucidated on the basis of spectroscopic studies (Lee et al., (2003a,b). The two racemic mixtures of phenylpropanoids 1-(4 -molhoxyphonyl)-(1 / , 2S and IS, 27 )-propanediol and l-(4 -methoxyphenyl)-(17 , 27 and IS, 2S)-propanediol] were isolated, along with two known phenylpropanoids. 

From the polar portion of the methanolic extract of the fruit of anise (P. anisum L.), Fujimatu et al. (2003) isolated aromatic compound glucosides and an alkyl glucoside. 

Fujimatu, E., Ishikawa, T. and Kitajima, J. (2003) Aromatic compound glucosides, alkyl glucoside and glucide from the fruit of anise. Phytochemistry 63(5), 609-616. 

Lirdprapamongkol K, Svasti J. Alkyl glucoside synthesis using Thai rosewood beta-glucosidase. Biotechnol. Lett. 2000 22 1889-1894. 

Whiddon, C.R. Soderman, O. Unusually large deuterium isotope effects in the phase diagram of a mixed alkyl-glucoside surfactant/water system. Langmuir 2001, 17, 1803-1806. 

Micelles and cyclodextrins are the most common reagents used for this technique. Micellar electrokinetic capillary chromatography (MECC or MEKC) is generally used for the separation of small molecules [6], Sodium dodecyl sulfate at concentrations from 20 to 150 mM in conjunction with 20 mM borate buffer (pH 9.3) or phosphate buffer (pH 7.0) represent the most common operating conditions. The mechanism of separation is related to reversed-phase liquid chromatography, at least for neutral solutes. Organic solvents such as 5-20% methanol or acetonitrile are useful to modify selectivity when there is too much retention in the system. Alternative surfactants such as bile salts (sodium cholate), cationic surfactants (cetyltrimethy-lammonium bromide), nonionic surfactants (poly-oxyethylene-23-lauryl ether), and alkyl glucosides can be used as well. 

The preparation of liposomes from mixed detergent/lipid micelles can also be done with other detergents, such as -alkyl-glucosides ( =6-9), octyl-thioglucoside or M-octanoyl-M-... 

U.S. 4,839,098 (1989) Wisotzki et al. (Henkel) Alkyl glucoside and dialkyl sulfosuccinate Improved detergency and foam stability on proteinaceous soils... 

U.S. 5,154,850 (1992) Deguchi et al. (Kao) Alkyl glucoside Reduced irritation and damage to hair and skin... 

Sottmann, T., Kluge, K., Strey, R., Reimer, J. and Soderman, O. (2002) General patterns ofthe phase behavior of mixtures of H20, alkanes, alkyl glucosides, and cosurfactants. Langmuir, 18, 3058-3067. 

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