Stigmastanol

Stigmastanol
Names
	IUPAC name 5α-Stigmastan-3β-ol
	Systematic IUPAC name (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
	Other names (3β)-Stigmastan-3-ol; (3β,5α)-Stigmastan-3-ol; β-Sitostanol; Dihydrositosterin; Dihydrositosterol; Dihydro-β-sitosterol; Fucostanol; Spinastanol; 24α-Ethylcholestanol
Identifiers
CAS Number	83-45-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:89400;
ChEMBL	ChEMBL252364;
ChemSpider	13078158;
ECHA InfoCard	100.001.345
PubChem CID	15559396;
UNII	C2NJ9WO6O7;
CompTox Dashboard (EPA)	DTXSID201016169 ;
	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;
Properties
Chemical formula	C29H52O
Molar mass	416.734 g·mol−1
Boiling point	139.4 to 139.8 °C (282.9 to 283.6 °F; 412.5 to 412.9 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.^[2]^[3]^[4] Animal studies suggest that it also inhibits biosynthesis of cholesterol in the liver.^[2]^{[verification needed]}

Stigmastanol is the product of the reduction of β-sitosterol^[5] and the hydrogenation of stigmasterol.^[6]

References

^ Sandqvist, Hakan; Bengtsson, Edvard (1931). "The empirical formula of sitosterol". Berichte der Deutschen Chemischen Gesellschaft B. 64: 2167–2171. doi:10.1002/cber.19310640849.
^ ^a ^b Batta, Ashok K.; Xu, Guorong; Honda, Akira; Miyazaki, Teruo; Salen, Gerald (2006). "Stigmasterol reduces plasma cholesterol levels and inhibits hepatic synthesis and intestinal absorption in the rat". Metabolism: Clinical and Experimental. 55 (3): 292–299. doi:10.1016/j.metabol.2005.08.024. PMID 16483871.
^ Heinemann T, Pietruck B, Kullak-Ublick G, von Bergmann K (1988). "Comparison of sitosterol and sitostanol on inhibition of intestinal cholesterol absorption". Agents and Actions. Supplements. 26: 117–122. PMID 3265272.
^ Heinemann T, Kullak-Ublick GA, Pietruck B, von Bergmann K (1991). "Mechanisms of action of plant sterols on inhibition of cholesterol absorption. Comparison of sitosterol and sitostanol". European Journal of Clinical Pharmacology. 40 (Suppl 1): S59–63. doi:10.1007/BF01409411. PMID 2044646. S2CID 23279253.
^ Thomasson Crompton, David William; Nickol, Brent B. (1985). Biology of the Acanthocephala. Cambridge University Press. p. 185. ISBN 9780521246743.
^ Paxena, P. B. (2007). Chemistry of Alkaloids. Discovery Publishing Hous. p. 231. ISBN 9788183563161.

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[1] Sandqvist, Hakan; Bengtsson, Edvard (1931). "The empirical formula of sitosterol". Berichte der Deutschen Chemischen Gesellschaft B. 64: 2167–2171. doi:10.1002/cber.19310640849.

[Batta2006-2] Batta, Ashok K.; Xu, Guorong; Honda, Akira; Miyazaki, Teruo; Salen, Gerald (2006). "Stigmasterol reduces plasma cholesterol levels and inhibits hepatic synthesis and intestinal absorption in the rat". Metabolism: Clinical and Experimental. 55 (3): 292–299. doi:10.1016/j.metabol.2005.08.024. PMID 16483871.

[3] Heinemann T, Pietruck B, Kullak-Ublick G, von Bergmann K (1988). "Comparison of sitosterol and sitostanol on inhibition of intestinal cholesterol absorption". Agents and Actions. Supplements. 26: 117–122. PMID 3265272.

[4] Heinemann T, Kullak-Ublick GA, Pietruck B, von Bergmann K (1991). "Mechanisms of action of plant sterols on inhibition of cholesterol absorption. Comparison of sitosterol and sitostanol". European Journal of Clinical Pharmacology. 40 (Suppl 1): S59–63. doi:10.1007/BF01409411. PMID 2044646. S2CID 23279253.

[5] Thomasson Crompton, David William; Nickol, Brent B. (1985). Biology of the Acanthocephala. Cambridge University Press. p. 185. ISBN 9780521246743.

[6] Paxena, P. B. (2007). Chemistry of Alkaloids. Discovery Publishing Hous. p. 231. ISBN 9788183563161.

[1]

[2]

[3]

[4]

[5]

[6]

v t e Phytosterols
C28	Brassicasterol Campesterol Ergosterol (Vitamin D2) Ergostenol Ergostatrienol Ergostadienol
C29	δ-7-avenasterol δ-5-avenasterol β-Sitosterol δ-7-stigmasterol Momordenol Spinasterol Stigmastanol Stigmastenol Stigmastadienol Stigmastadienone Stigmasterol Stigmastenone

See also

References