Lipase Catalyzed Kinetic Resolution of rac-2-(3-Methoxy-4-methylphenyl) propan-1-ol and rac-2-(3-Hydroxy-4-methylphenyl)propyl propanoate for S-(+)-Xanthorrhizol

Authors
Shafioul, Azam Sharif MohammedCheong, Chan Seong
Issue Date
2012-02-20
Publisher
KOREAN CHEMICAL SOC
Citation
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, v.33, no.2, pp.409 - 414
Abstract
Xanthorrhizol is a bisabolane type of natural sesquiterpene, the major component of essential oils of Curcuma xanthorrhiza. 2-(3-Methoxy-4-methylphenyl)propan-1-ol and 2-(3-hydroxy-4-methyl phenyl)propan-1-ol could be essential building block for enantioselective synthesis of xanthorrhizol. Enantioselective (c = 53%, E = 80 +/- 3) for R-(+)-2-(3-hydroxy-4-methylphenyl) propan-1-ol and (c = 58%, E = 27 +/- 1) for R-(+)-2-(3-methoxy-4-methylphenyl) propan-1-ol resolution processes were developed via lipase-catalyzed reaction. We found lipase Aspergillus oryzae (AOL) and Porcine pancreas (PPL) are selective to transesterification and hydrolysis in organic and aqueous phase. Modified demethylated substrate is appropriate for enantioselective hydrolysis reaction without any additives. Enantiopure chiral alcohol was crystallized from ethyl acetate/n-hexane co-solvent system. Gram scale resolved chiral intermediate will facilitate the synthesis of the unnatural S-(+)-xanthorrhizol, the corresponding isomer of the natural one.
Keywords
CURCUMA-XANTHORRHIZA; ENANTIOMERIC RATIO; SESQUITERPENES; CURCUMA-XANTHORRHIZA; ENANTIOMERIC RATIO; SESQUITERPENES; Lipase; Sesquiterpene; Xanthorrhizol; Transesterification; Hydrolysis
ISSN
0253-2964
URI
https://pubs.kist.re.kr/handle/201004/129533
DOI
10.5012/bkcs.2012.33.2.409
Appears in Collections:
KIST Article > 2012
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