ergostane

{{Chembox

| ImageFile = Ergostane.svg

| ImageSize = 200px

| ImageAlt =

| IUPACName = Ergostane

| SystematicName = (1R,3aS,3bR,5aΞ,9aS,9bS,11aR)-1-[(2R,5S)-5,6-Dimethylheptan-2-yl]-9a,11a-dimethylhexadecahydro-1H-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 =

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Ergostane is a tetracyclic triterpene, also known as 24S-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.{{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}}{{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}} 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.{{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}}