161275-87-2Relevant academic research and scientific papers
LIPASE CATALYZED REACTIONS AND STRATEGY FOR ALCOHOL RESOLUTION
Langrand, Georges,Baratti, Jaquess,Buono, Gerard,Triantaphylides, Christian
, p. 29 - 32 (1986)
Asymmetric hydrolysis, ester interchange and ester formation were carried out for menthol resolution with Candida cylindracea lipase.The reactions were realized under emulsified conditions with water soluble enzyme and in organic medium with an insoluble enzyme preparation.In the latter case, an enhancement of the enantioselectivity was observed.The potentialities of ester interchange and ester formation for preparative alcohol resolutions are discussed.
d-menthol fatty acid ester derivative, application thereof and preparation method for d-menthol fatty acid ester derivative
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, (2017/08/29)
The invention belongs to the technical field of medicines and relates to a d-menthol fatty acid ester derivative, an application thereof and a preparation method for the d-menthol fatty acid ester derivative. The d-terpineol fatty acid ester is prepared through carrying out an esterification reaction on d-menthol and straight-chain fatty acid. The method comprises the steps of firstly, carrying out a reaction on fatty acid and thionyl chloride so as to prepare acyl chloride, and then, subjecting acyl chloride to a reaction with d-menthol, there by preparing the ester. The d-menthol ester is applied to external preparations such as plasters, cataplasm, ointment, gels, sprays and liniment as a penetration enhancer, so that the percutaneous absorption capacity of drugs, particularly, chiral drug enantiomers is increased; and the d-menthol ester is a very good percutaneous absorption penetration enhancer and has a broad application prospect.
Thermodynamics of the lipase-catalyzed esterification of 1-dodecanoic acid with (-)-menthol in organic solvents
Tewari, Yadu B.,Schantz, Michele M.,Vanderah, David J.
, p. 641 - 647 (2007/10/03)
The thermodynamics of the lipase-catalyzed stereospecific esterification of 1-dodecanoic acid with (-)- menthol in seven organic solvents have been investigated. Equilibrium measurements were performed using hexane, heptane, cyclohexane, toluene, 2,2,4-trimethylpentane, acetonitrile, and 2-methyl-2-butanol at the temperature T = 298.15 K. The equilibrium constants have been correlated with the (octanol + water) partition coefficients and the relative permittivities of the solvents. The saturation molalities and the (hexane + water) partition coefficients of (-)-menthol, 1-dodecanoic acid, and (-)-menthyl dodecanoate have also been determined at T = 298.15 K. The equilibrium constant of the esterification reaction in aqueous media has been calculated. An important finding is that the molality of water plays an important role in determining the extent of ester formation. In acetonitrile and 2-methyl-2-butanol, which have a very high molality of water, the formation of (-)-methyl dodecanoate is considerably smaller. However, in hydrophobic solvents with lower molalities of water, the formation of (-)-methyl dodecanoate is favored in the reaction mixture. The value of the equilibrium constant varies from 3 to 26. However, the molality of (-)-methyl dodecanoate changes from 0.034 mmol kg-1 in acetonitrile to 16 mmol kg-1 in heptane. The change in product yield is a factor of ≈500 and is a striking example of the utility of organic solvents in biocatalysis.
Candida Rugosa lipase: Enantioselectivity enhancements in organic solvents
Persichetti, Rose A.,Lalonde, Jim J.,Govardhan, Chandrika P.,Khalaf, Nazer K.,Margolin, Alexey L.
, p. 6507 - 6510 (2007/10/03)
Chiral resolutions of carboxylic acids (1-3) and alcohol (4) were carried out through esterification or transesterification in organic solvents using cross-linked enzyme crystals (CLEC) of Candida rugosa lipase (CRL). Comparison of these results with those of crude CRL reveal significant differences. As was seen in resolution through hydrolysis, a marked improvement in enantioselectivity is realized with the CLEC. Additionally, the stability afforded the enzyme in CLEC form leads to a higher activity in organic solvent.
Quantitative Analyses of Biochemical Kinetic Resolution of Enantiomers. 2. Enzyme-Catalyzed Esterification in Water-Organic Solvent Biphasic Systems
Chen, Ching-Shih,Wu, Shih-Hsiung,Girdaukas, Gary,Sih, Charles J.
, p. 2812 - 2817 (2007/10/02)
New quantitative expressions, which relate the kinetic and thermodynamic parameters that govern the stereospecificity of enzyme-catalyzed resolution of enantiomers in biphasic aqueous-organic media, have been developed.The theoretical predictions have been verified experimentally, and the technical merit of this esterification methodology has been assessed in relation to the more conventional hydrolytic procedure.
