Method for esterification of (S)-citronellol using lipase in sup

Chemistry: molecular biology and microbiology – Process of utilizing an enzyme or micro-organism to destroy... – Resolution of optical isomers or purification of organic...

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435135, C12P 4100, C12P 762

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active

054037395

ABSTRACT:
A primary terpene alcohol such as citronellol can be enzymatically esterified with a higher fatty acid such as oleic acid in the presence of lipase in an atmosphere of supercritical carbon dioxide as the reaction medium at a high reaction velocity. The influence of the temperature and pressure of the atmosphere on the reaction velocity was studied. When the starting primary terpene alcohol is a racemic compound of the optical isomers having chirality as in (.+-.)-citronellol, efficient racemic resolution can be achieved by suitably selecting the temperature and pressure in the vicinity of the critical point of carbon dioxide to give the (S)-(-)-ester having an optical purity of almost 100% when the starting terpene alcohol is (.+-.)-citronellol.

REFERENCES:
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Grant and Hackh's Chemical Dictionary, p. 580.
Ikushima, Y., et al., Chem. Soc. Japan-Chem. Lett. 1:109-112 (1993).
Steytler, D. C. et al., Enzyme Microb. Technol. 13:221-6 (1991).
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Langrand, G. et al., Biotechnol. Lett. 12:581-6 (1990).
K. Nakamura, TIBTECH, vol. 8, pp. 288-292 (1990).
M. H. Vermue et al., "Enzyme Microb. Technol.", vol. 14, pp. 649-655 (1992).

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