Misplaced Pages

Apocholic acid

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Apocholic acid
Names
IUPAC name 3α,12α-Dihydroxy-5β-chol-8(14)-en-24-oic acid
Systematic IUPAC name (4R)-4-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
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: XWJTYEGVQBFZHI-IMPNNSMHSA-N
SMILES
  • C(CCC(O)=O)1()CCC2=C3CC4()C(O)CC4(C)C3C(O)21C
Properties
Chemical formula C24H38O4
Molar mass 390.564 g·mol
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Apocholic acid is an unsaturated bile acid first characterized in the 1920s. It has questionable carcinogenic activity as experimentally, sarcomas were induced in mice with injection of deoxycholic acid.

The salts and esters of apocholic acid are known as apocholates.

Structure of sodium apocholate

See also

References

  1. |ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC Apocholic acid at Sigma-Aldrich
  2. 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.
  3. 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.

External links

Categories: