Apocholic acid

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 desoxycholic acid. [3]

Apocholic acid[1]

Names
IUPAC name (4R)-4-[(3R,5R,9R,10S,12S,13R,17R)-3,12-Dihydroxy-10,13-dimethyl-2,3,4,5,6,7,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
Other names 3α,12α-Dihydroxy-5β,8(14)-cholen-24-oic acid; 3α,12α-Dihydroxy-5β-chol-8(14)en-24-oic acid; 5β,8(14)-Cholen-24-oic acid-3α,12α-diol
Identifiers
CAS Number	641-81-6^Y 63949-02-0 (sodium apocholate)^Y
3D model (JSmol)	Interactive image
ChemSpider	91993^Y
PubChem CID	101818
UNII	MZW7515V5Z^Y U2L03X5GY0 (sodium apocholate)^Y
CompTox Dashboard (EPA)	DTXSID00214307
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/s1^Y Key: XWJTYEGVQBFZHI-IMPNNSMHSA-N^Y
SMILES 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
Chemical formula	C23H38O4
Molar mass	378.553 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).
N verify (what is ^YN ?)
Infobox references

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

Structure of sodium apocholate

See also

• Apocholate citrate agar

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.

External links

• 5-beta-Chol-8(14)-en-24-oic acid, 3-alpha,12-alpha-dihydroxy-, sodium salt at environmentalchemistry.com