Stigmastanol

{{Chembox

| ImageFile = Stigmastanol.svg

| ImageSize =

| IUPACName = 5α-Stigmastan-3β-ol

| SystematicName = (1R,3aS,3bR,5aS,7S,9aS,9bS,11aR)-1-[(2R,5R)-5-Ethyl-6-methylheptan-2-yl]-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-ol

| OtherNames = (3β)-Stigmastan-3-ol; (3β,5α)-Stigmastan-3-ol; β-Sitostanol; Dihydrositosterin; Dihydrositosterol; Dihydro-β-sitosterol; Fucostanol; Spinastanol; 24α-Ethylcholestanol

|Section1={{Chembox Identifiers

| CASNo = 83-45-4

| CASNo_Ref = {{cascite|correct|CAS}}

| PubChem = 15559396

| ChEBI = 89400

| ChEMBL = 252364

| ChemSpiderID = 13078158

| UNII = C2NJ9WO6O7

| SMILES = O[C@H]1CC[C@@]2(C)[C@](CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@@H](CC[C@@H](CC)C(C)C)C)([H])C1

| InChI =

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|Section2={{Chembox Properties

| C=29 | H=52 | O=1

| Appearance =

| Density =

| MeltingPt =

| BoilingPtC = 139.4 to 139.8

| BoilingPt_ref = {{cite journal | title = The empirical formula of sitosterol |author1=Sandqvist, Hakan |author2=Bengtsson, Edvard | journal = Berichte der Deutschen Chemischen Gesellschaft B | year = 1931 | volume = 64 | pages = 2167–2171|doi=10.1002/cber.19310640849 }}

| Solubility =

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|Section3={{Chembox Hazards

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Stigmastanol (sitostanol) is a phytosterol found in a variety of plant sources. Similar to sterol esters and stanol esters, stigmastanol inhibits the absorption of cholesterol from the diet.{{cite journal |author1=Batta, Ashok K. |author2=Xu, Guorong |author3=Honda, Akira |author4=Miyazaki, Teruo |author5=Salen, Gerald | title = Stigmasterol reduces plasma cholesterol levels and inhibits hepatic synthesis and intestinal absorption in the rat | journal = Metabolism: Clinical and Experimental | year = 2006 | volume = 55 | issue = 3 | pages = 292–299 | doi=10.1016/j.metabol.2005.08.024|pmid=16483871 }}{{cite journal |vauthors=Heinemann T, Pietruck B, Kullak-Ublick G, von Bergmann K | title = Comparison of sitosterol and sitostanol on inhibition of intestinal cholesterol absorption | journal = Agents and Actions. Supplements | year = 1988 | volume = 26 | pages = 117–122 | pmid = 3265272}}{{cite journal | doi = 10.1007/BF01409411 |vauthors=Heinemann T, Kullak-Ublick GA, Pietruck B, von Bergmann K | title = Mechanisms of action of plant sterols on inhibition of cholesterol absorption. Comparison of sitosterol and sitostanol | journal = European Journal of Clinical Pharmacology | year = 1991 | volume = 40 | issue = Suppl 1 | pages = S59–63 | pmid = 2044646|s2cid=23279253 }} Animal studies suggest that it also inhibits biosynthesis of cholesterol in the liver.{{verification needed|date=April 2015}}

Stigmastanol is the product of the reduction of β-sitosterol{{cite book|last1=Thomasson Crompton|first1=David William|last2=Nickol|first2=Brent B.|title=Biology of the Acanthocephala|date=1985|publisher=Cambridge University Press|isbn=9780521246743|page=185|url=https://books.google.com/books?id=GPY8AAAAIAAJ&q=stigmastanol&pg=PA185}} and the hydrogenation of stigmasterol.{{cite book|last1=Paxena|first1=P. B.|title=Chemistry of Alkaloids|date=2007|publisher=Discovery Publishing Hous|isbn=9788183563161|page=231|url=https://books.google.com/books?id=zZB21wSZpyUC&q=stigmastanol+reduction&pg=PA231}}