Stigmastane

Stigmastane
Names
IUPAC name
5ξ-Stigmastane[1]
Systematic IUPAC name
(1R,3aS,3bR,5aΞ,9aS,9bS,11aR)-1-[(2R,5R)-5-Ethyl-6-methylheptan-2-yl]-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
3D model (JSmol)
8170826
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C29H52/c1-7-22(20(2)3)12-11-21(4)25-15-16-26-24-14-13-23-10-8-9-18-28(23,5)27(24)17-19-29(25,26)6/h20-27H,7-19H2,1-6H3/t21-,22-,23?,24+,25-,26+,27+,28+,29-/m1/s1
    Key: GKBHKNPLNHLYHT-LWQAOISPSA-N
  • CC[C@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4[C@@]3(CCCC4)C)C)C(C)C
Properties
C29H52
Molar mass 400.735 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Stigmastane or 24R-ethylcholestane is a tetracyclic triterpene, along with cholestane and ergostane, this sterane is used as a biomarker for early eukaryotes.[2]

  • 5α-Stigmastane
    5α-Stigmastane
  • 5β-Stigmastane
    5β-Stigmastane

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. 1531. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ Brocks, Jochen J.; Jarrett, Amber J. M.; Sirantoine, Eva; Hallmann, Christian; Hoshino, Yosuke; Liyanage, Tharika (2017). "The rise of algae in Cryogenian oceans and the emergence of animals". Nature. 548 (7669): 578–581. Bibcode:2017Natur.548..578B. doi:10.1038/nature23457. PMID 28813409. S2CID 205258987.

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