Ergostane

Ergostane
Names
	Preferred 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
CAS Number	25318-39-2; 511-20-6 (5α)-ergostane;
3D model (JSmol)	Interactive image; (5α)-ergostane: Interactive image;
ChemSpider	144332 (5α)-ergostane;
PubChem CID	6857535; 164641 (5α)-ergostane;
UNII	Y0XC723P4C (5α)-ergostane ;
CompTox Dashboard (EPA)	DTXSID70948162 ;
	InChI 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;
	SMILES 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
Chemical formula	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). Infobox references

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.^[1]^[2] 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]

References

^ 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.
^ 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.
^ 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.

[Glotter1991-1] 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.

[KirsonGlotter1981-2] 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.

[1]

[2]

[3]

See also

References