Cholane

Cholane
Names
IUPAC name
Cholane[1]
Systematic IUPAC name
(1R,3aS,3bR,5aΞ,9aS,9bS,11aR)-9a,11a-Dimethyl-1-[(2R)-pentan-2-yl]hexadecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • 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 checkY
    Key: QSHQKIURKJITMZ-BRPMRXRMSA-N checkY
  • 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
  • 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
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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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).[2] 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.