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Cholane

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Cholane
Names
IUPAC name Cholane
Systematic IUPAC name (1R,3aS,3bR,5aΞ,9aS,9bS,11aR)-9a,11a-Dimethyl-1-hexadecahydro-1H-cyclopentaphenanthrene
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: QSHQKIURKJITMZ-BRPMRXRMSA-N
  • 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/s1Key: QSHQKIURKJITMZ-BRPMRXRMBN
SMILES
  • CCC(C)1CC21(CC32CC43(CCCC4)C)C
  • C41CCCC1(3(2CC(2(C)CC3)(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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Cholane is a triterpene which can exist as either of two stereoisomers, 5α-cholane and 5β-cholane. Its name is derived from Greek: χολή (chole) meaning 'bile' in reference to its original discovery from the bile of the American bullfrog (Rana catesbeiana). 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 5α-Cholane
  • 5β-Cholane 5β-Cholane

See also

References

  1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1528. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. 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

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