Stigmastanol

{{Chembox | ImageFile = Stigmastanol.svg | ImageSize = | IUPACName = 5α-Stigmastan-3β-ol | SystematicName = (1''R'',3a''S'',3b''R'',5a''S'',7''S'',9a''S'',9b''S'',11a''R'')-1-[(2''R'',5''R'')-5-Ethyl-6-methylheptan-2-yl]-9a,11a-dimethylhexadecahydro-1''H''-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 = 19466-47-8 | CASNo_Ref = {{Cascite|changed|CAS}} | CASNo1 = 83-45-4 | CASNo1_Ref = {{cascite|correct|CAS}} | PubChem = 15559396 | ChEBI = 89400 | ChEMBL = 252364 | ChemSpiderID = 13078158 | UNII = C2NJ9WO6O7 | StdInChI=1S/C29H52O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h19-27,30H,7-18H2,1-6H3/t20-,21-,22?,23+,24+,25-,26+,27+,28+,29-/m1/s1 | StdInChIKey = LGJMUZUPVCAVPU-KZXGMYDKSA-N | 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 }} |Section2={{Chembox Properties | C=29 | H=52 | O=1 | Appearance = | Density = | MeltingPt = | BoilingPtC = 139.4 to 139.8 | BoilingPt_ref = <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 }}</ref> | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}

'''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.<ref name="Batta2006">{{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 }}</ref><ref>{{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}}</ref><ref>{{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 }}</ref> Animal studies suggest that it also inhibits biosynthesis of cholesterol in the liver.<ref name="Batta2006" />{{verification needed|date=April 2015}}

Stigmastanol is the product of the reduction of β-sitosterol<ref>{{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}}</ref> and the hydrogenation of stigmasterol.<ref>{{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}}</ref>

== See also == * Stigmasterol, a closely related sterol

== References == {{reflist}}

Category:Phytosterols