Stigmastanol

Stigmastanol
Names
	IUPAC name (3S,5S,8R,9S,10S,13R,14S,17R)-17-((2R,5R)-5-ethyl-6-methylheptan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-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;
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	139.4–139.8 °C
	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, stigmasterol 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]

References

^ Sandqvist, Hakan; Bengtsson, Edvard (1931). "The empirical formula of sitosterol". Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen. 64B: 2167–2171.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ ^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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Heinemann T; Kullak-Ublick G A; 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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[1] Sandqvist, Hakan; Bengtsson, Edvard (1931). "The empirical formula of sitosterol". Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen. 64B: 2167–2171.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[4] Heinemann T; Kullak-Ublick G A; 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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See also

References