Apocholic acid is an unsaturated bile acid first characterized in the 1920s.[2] It has questionable carcinogenic activity as experimentally, sarcomas were induced in mice with injection of deoxycholic acid. [3]
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IUPAC name
3α,12α-Dihydroxy-5β-chol-8(14)-en-24-oic acid
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Systematic IUPAC name
(4R)-4-[(1R,5aR,7R,9aS,9bR,11S,11aR)-7,11-Dihydroxy-9a,11a-dimethyl-2,3,4,5,5a,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid | |
Other names
3α,12α-Dihydroxy-5β,8(14)-cholen-24-oic acid; 5β,8(14)-Cholen-24-oic acid-3α,12α-diol
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Identifiers | |
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3D model (JSmol)
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ChemSpider | |
PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |
C24H38O4 | |
Molar mass | 390.564 g·mol−1 |
Melting point | 175 to 176 °C (347 to 349 °F; 448 to 449 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The salts and esters of apocholic acid are known as apocholates.[citation needed]
See also
editReferences
edit- ^ |ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC Apocholic acid[permanent dead link ] at Sigma-Aldrich
- ^ Boedecker, F.; Volk, H. (1922). "Unsaturated bile acids. III. Relations of apocholic acid, dihydroxycholenic acid (m. 260) and cholic acid to desoxycholic acid". Berichte der Deutschen Chemischen Gesellschaft B. 55: 2302–2309. doi:10.1002/cber.19220550810.
- ^ Lacassagne, A (June 10, 1961). "Carcinogenic activity of apocholic acid". Nature. 190 (4780): 1007–8. Bibcode:1961Natur.190.1007L. doi:10.1038/1901007a0. PMID 13831121. S2CID 4175440.