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Chemical Compound Review:

CHEBI:33197 (10R)-10-hydroxyoctadecanoic acid

Synonyms: AC1L1ZRO, LMFA02000237, C03195, (R)-10-Hydroxystearate, (R)-10-hydroxystearic acid, ...

Gotouda, H. et al., Hudson, J.A. et al., Adachi, J. et al., el-Sharkawy, S.H. et al., Kuo, T.M. et al., et al.

Adachi, Ueno, Miwa, Asano, Nishimura, Tatsuno,

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Disease relevance of C03195

Cystic fibrosis and bacterial conversion of oleic acid to a cathartic, 10-hydroxystearic acid [1].
We detected hydroxy fatty acids (10-hydroxyoctadecanoic acid and 10-hydroxyhexadecanoic acid) as well as 10-ketooctadecanoic acid in adipocere, but not in the control [2].
Production of 10-ketostearic acid and 10-hydroxystearic acid by strains of Sphingobacterium thalpophilum isolated from composted manure [3].
The enzyme preparations from Flavobacterium meningosepticum solubilized by sonication catalyzed not only hydration of oleic acid to produce 10-hydroxystearic acid but dehydrogenation of this product [4].

High impact information on C03195

Resting cells of Saccharomyces cerevisiae (baker's yeast, type II; Sigma) were used to convert oleic acid into 10-hydroxyoctadecanoic acid with a 45% yield [5].
One 10-hydroxystearic-acid-producing bacterial group was represented by two strains of an anaerobic gram-negative curved rod with tufts of flagella on the concave surface of the cell [6].

References

Cystic fibrosis and bacterial conversion of oleic acid to a cathartic, 10-hydroxystearic acid. Campbell, I.M., Crozier, D.N., Trim, A., Sigrist, J. Lancet (1987) [Pubmed]
Epicoprostanol found in adipocere from five human autopsies. Adachi, J., Ueno, Y., Miwa, A., Asano, M., Nishimura, A., Tatsuno, Y. Lipids (1997) [Pubmed]
Production of 10-ketostearic acid and 10-hydroxystearic acid by strains of Sphingobacterium thalpophilum isolated from composted manure. Kuo, T.M., Lanser, A.C., Nakamura, L.K., Hou, C.T. Curr. Microbiol. (2000) [Pubmed]
The mechanism of experimental adipocere formation: hydration and dehydrogenation in microbial synthesis of hydroxy and oxo fatty acids. Gotouda, H., Takatori, T., Terazawa, K., Nagao, M., Tarao, H. Forensic Sci. Int. (1988) [Pubmed]
Microbial oxidation of oleic acid. el-Sharkawy, S.H., Yang, W., Dostal, L., Rosazza, J.P. Appl. Environ. Microbiol. (1992) [Pubmed]
Conversion of oleic acid to 10-hydroxystearic acid by two species of ruminal bacteria. Hudson, J.A., MacKenzie, C.A., Joblin, K.N. Appl. Microbiol. Biotechnol. (1995) [Pubmed]

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