Article · Wikipedia archive · Last revised Jul 7, 2026

Ergostane

Ergostane is a tetracyclic triterpene, also known as 24S-methylcholestane. The compound itself has no known uses; however various functionalized analogues are produced by plants and animals. The most important of these are the heavily derivatised withanolides. However simpler forms do exist, such as the sterane campestane (24R-methylcholestane). Along with cholestane and stigmastane, this sterane is used as a biomarker for early eukaryotes.

Last revised
Jul 7, 2026
Read time
≈ 1 min
Length
225 w
Citations
3
Source
Wikipedia ↗
Ergostane
source ↗
Names
IUPAC name
Ergostane
Systematic IUPAC name
(1R,3aS,3bR,5aΞ,9aS,9bS,11aR)-1-[(2R,5S)-5,6-Dimethylheptan-2-yl]-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C28H50/c1-19(2)20(3)10-11-21(4)24-14-15-25-23-13-12-22-9-7-8-17-27(22,5)26(23)16-18-28(24,25)6/h19-26H,7-18H2,1-6H3/t20-,21+,22+,23-,24+,25-,26-,27-,28+/m0/s1
    Key: WAAWMJYYKITCGF-WTPIMUJOSA-N
  • InChI=1S/C28H50/c1-19(2)20(3)10-11-21(4)24-14-15-25-23-13-12-22-9-7-8-17-27(22,5)26(23)16-18-28(24,25)6/h19-26H,7-18H2,1-6H3/t20-,21+,22?,23-,24+,25-,26-,27-,28+/m0/s1
    Key: WAAWMJYYKITCGF-ADGVWNIHSA-N
  • C[C@H](CC[C@H](C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4[C@@]3(CCCC4)C)C
  • (5α)-ergostane: C[C@H](CC[C@H](C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CCCC4)C)C
Properties
C28H50
Molar mass 386.708 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ergostane is a tetracyclic triterpene, also known as 24S-methylcholestane. The compound itself has no known uses; however various functionalized analogues are produced by plants and animals. The most important of these are the heavily derivatised withanolides.12 However simpler forms do exist, such as the sterane campestane (24R-methylcholestane). Along with cholestane and stigmastane, this sterane is used as a biomarker for early eukaryotes.3

See also

See also

References

References

  1. Glotter, E. (1991). "Withanolides and related ergostane-type steroids". Natural Product Reports. 8 (4): 415–40. doi:10.1039/np9910800415. ISSN 0265-0568. PMID 1787922.
  2. Kirson, Isaac; Glotter, Erwin (1981). "Recent Developments in Naturally Occurring Ergostane-Type Steroids. A Review". Journal of Natural Products. 44 (6): 633–647. doi:10.1021/np50018a001. ISSN 0163-3864.
  3. 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.