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 NumberNY

3D model (JSmol)

PubChem CID

CompTox Dashboard (EPA)

InChI InChI=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/s1Key: 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

Properties

Chemical formulaC29H52O

Molar mass416.734 g·mol−1

Boiling point139.4 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. Animal studies suggest that it also inhibits biosynthesis of cholesterol in the liver.[verification needed]

Stigmastanol is the product of the reduction of β-sitosterol and the hydrogenation of stigmasterol.

Stigmastanol

See also