Cholane

Cholane is a triterpene which can exist as either of two stereoisomers, 5α-cholane and 5β-cholane. Its name is derived from the Greek work for bile (χολή, chole) in reference to its original discovery from the bile of the American bullfrog (Rana catesbeiana).[1] The compound itself has no known uses; however, various functionalized analogues are produced by plants and animals, typically in the form of sterols, steroids and bile acids (e.g. cholic acid).

• 
  5α-Cholane
• 
  5β-Cholane

Cholane

Names
IUPAC name (5S,8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-17-[(1R)-1-methylbutyl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
CAS Number	80373-86-0^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:35519^Y
ChemSpider	5256866^Y
PubChem CID	6857530
UNII	6EF0441D4P^N
CompTox Dashboard (EPA)	DTXSID00203291
InChI InChI=1S/C24H42/c1-5-8-17(2)20-12-13-21-19-11-10-18-9-6-7-15-23(18,3)22(19)14-16-24(20,21)4/h17-22H,5-16H2,1-4H3/t17-,18?,19+,20-,21+,22+,23+,24-/m1/s1^Y Key: QSHQKIURKJITMZ-BRPMRXRMSA-N^Y InChI=1/C24H42/c1-5-8-17(2)20-12-13-21-19-11-10-18-9-6-7-15-23(18,3)22(19)14-16-24(20,21)4/h17-22H,5-16H2,1-4H3/t17-,18?,19+,20-,21+,22+,23+,24-/m1/s1 Key: QSHQKIURKJITMZ-BRPMRXRMBN
SMILES CCC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CCCC4)C)C C41CCCC[C@@]1([C@@H]3[C@H]([C@@H]2CC[C@@H]([C@@]2(C)CC3)[C@H](C)CCC)CC4)C
Properties
Chemical formula	C24H42
Molar mass	330.59 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

See also

• Cholestane
• Ergostane

References

1. Kurauti, Yukiti; Kazuno, Taro (January 1939). "Tetraoxycholan, Trioxycholen und Trioxy-bis-norsterocholansäure aus der Galle von Rana Catesbina Shaw". Hoppe-Seyler's Zeitschrift für physiologische Chemie (in German). 262 (1–2): 53–60. doi:10.1515/bchm2.1939.262.1-2.53.

External links

• Cholanes at the US National Library of Medicine Medical Subject Headings (MeSH)