Stigmastanol

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

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 Y
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)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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

See also

• Stigmasterol, a closely related sterol