{{Chembox | ImageFile = Ergostane.svg | ImageSize = 200px | ImageAlt = | IUPACName = Ergostane | SystematicName = (1''R'',3a''S'',3b''R'',5a''Ξ'',9a''S'',9b''S'',11a''R'')-1-[(2''R'',5''S'')-5,6-Dimethylheptan-2-yl]-9a,11a-dimethylhexadecahydro-1''H''-cyclopenta[''a'']phenanthrene | OtherNames = |Section1={{Chembox Identifiers | CASNo = 25318-39-2 | CASNo1 = 511-20-6 | CASNo1_Comment = (5α)-ergostane | UNII1_Ref = {{fdacite|correct|FDA}} | UNII1 = Y0XC723P4C | UNII1_Comment = (5α)-ergostane
| PubChem = 6857535 | 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 | InChIKey= 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 | SMILES_Comment = | PubChem1 = 164641 | PubChem1_Comment = (5α)-ergostane | ChemSpiderID = 144332 | ChemSpiderID_Comment = (5α)-ergostane | SMILES1 = 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 | SMILES1_Comment = (5α)-ergostane | StdInChI = 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 | StdInChI_Comment = (5α)-ergostane | StdInChIKey = WAAWMJYYKITCGF-WTPIMUJOSA-N }} |Section2={{Chembox Properties | C=28 | H=50 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Ergostane''' is a tetracyclic triterpene, also known as 24''S''-methylcholestane. The compound itself has no known uses;{{cn|date=September 2023}} however various functionalized analogues are produced by plants and animals. The most important of these are the heavily derivatised withanolides.<ref name="Glotter1991">{{cite journal|last1=Glotter|first1=E.|title=Withanolides and related ergostane-type steroids|journal=Natural Product Reports|volume=8|issue=4|year=1991|pages=415–40|issn=0265-0568|doi=10.1039/np9910800415|pmid=1787922}}</ref><ref name="KirsonGlotter1981">{{cite journal|last1=Kirson|first1=Isaac|last2=Glotter|first2=Erwin|title=Recent Developments in Naturally Occurring Ergostane-Type Steroids. A Review|journal=Journal of Natural Products|volume=44|issue=6|year=1981|pages=633–647|issn=0163-3864|doi=10.1021/np50018a001}}</ref> However simpler forms do exist, such as the sterane campestane (24''R''-methylcholestane). Along with cholestane and stigmastane, this sterane is used as a biomarker for early eukaryotes.<ref>{{Cite journal|last1=Brocks|first1=Jochen J.|last2=Jarrett|first2=Amber J. M.|last3=Sirantoine|first3=Eva|last4=Hallmann|first4=Christian|last5=Hoshino|first5=Yosuke|last6=Liyanage|first6=Tharika|title=The rise of algae in Cryogenian oceans and the emergence of animals|journal=Nature|volume=548|issue=7669|pages=578–581|doi=10.1038/nature23457|pmid=28813409|year=2017|bibcode=2017Natur.548..578B|s2cid=205258987}}</ref>
==See also== * Cholane * Cholestane * Lanostane
==References== {{Reflist}}
Category:Triterpenes Category:Biomarkers Category:Tetracyclic compounds