Abstract
Cinerone [2-(2′-cis-butenyl)-3-methyl-2-cyclopenten-1-one] is hydroxylated to cinerolone [2-(2′-cis-butenyl)-3-methyl-4-hydroxy-2-cyclopenten-1-one] by a number of streptomycetes, bacteria, and fungi. Aspergillus niger ATCC 9,142 and Streptomyces aureofaciens ATCC 10,762 were found to be the most effective hydroxylators. The optical activity of the product was found to range from [α]D25 0° to -8.6°, depending on the organism and conditions of culture. Two additional hydroxylated products of cinerone have been isolated and identified as 2-n-butyl-4-hydroxy-3-methyl-2-cyclopenten-1-one and 2-(2′-cis-butenyl-4′-hydroxy)-3-methyl-2-cyclopenten-1-one, respectively.
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- Bhattacharyya P. K., Ganapathy K. Microbiological transformations of terpenes. VI. Studies on the mechanism of some fungal hydroxylation reactions with the aid of model systems. Indian J Biochem. 1965 Sep;2(3):137–145. [PubMed] [Google Scholar]
- CROMBIE L., ELLIOTT M. Chemistry of the natural pyrethrins. Fortschr Chem Org Naturst. 1961;19:120–164. doi: 10.1007/978-3-7091-7156-1_3. [DOI] [PubMed] [Google Scholar]
- Prema B. R., Bhattacharyya P. K. Microbiological Transformation of Terpenes: II. Transformation of alpha-Pinene. Appl Microbiol. 1962 Nov;10(6):524–528. doi: 10.1128/am.10.6.524-528.1962. [DOI] [PMC free article] [PubMed] [Google Scholar]