# Ergostane

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Ergostane
> Markdown URL: https://mediated.wiki/source/Ergostane.md
> Source: https://en.wikipedia.org/wiki/Ergostane
> Source revision: 1174955252
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{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](/source/tetracyclic) [triterpene](/source/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 [withanolide](/source/withanolide)s.<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](/source/sterane) [campestane](/source/campestane) (24''R''-methylcholestane). Along with [cholestane](/source/cholestane) and [stigmastane](/source/stigmastane), this sterane is used as a [biomarker](/source/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](/source/Cholane)
* [Cholestane](/source/Cholestane)
* [Lanostane](/source/Lanostane)

==References==
{{Reflist}}

Category:Triterpenes
Category:Biomarkers
Category:Tetracyclic compounds

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Adapted from the Wikipedia article [Ergostane](https://en.wikipedia.org/wiki/Ergostane) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Ergostane?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.