Apocholic acid

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Apocholic acid[1]
File:Apocholic acid.svg
Names
IUPAC name
3α,12α-Dihydroxy-5β-chol-8(14)-en-24-oic acid
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
Identifiers
3D model (JSmol)
ChemSpider
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UNII
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  • InChI=1S/C24H38O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-16,18,20-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,18-,20+,21+,23+,24-/m1/s1 checkY
    Key: XWJTYEGVQBFZHI-IMPNNSMHSA-N checkY
  • C[C@H](CCC(O)=O)[C@@]1([H])CCC2=C3CC[C@]4([H])C[C@H](O)CC[C@]4(C)C3C[C@H](O)[C@@]21C
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).

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]

The salts and esters of apocholic acid are known as apocholates.[citation needed]

File:Sodium apocholate.svg
Structure of sodium apocholate

See also

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References

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  1. ^ |ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC Apocholic acid[permanent dead link] at Sigma-Aldrich
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