stigmastanol

Also known as sitostanol, fucostanol, (3S,5S,8R,9S,10S,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

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.

Chemical data

Formula: C29H52O
Molecular weight: 416.7 g/mol
IUPAC name: (3S,5S,8R,9S,10S,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
SMILES: CC[C@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@@H](C4)O)C)C)C(C)C
InChIKey: LGJMUZUPVCAVPU-HRJGVYIJSA-N
XLogP: 10.2
Polar surface area: 20.2 Å²
H-bond donors: 1
H-bond acceptors: 1
Formal charge: 0

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Drug data · ChEMBL

Molecule type: Small molecule

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Research

206 papers

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Wikidata facts

Mass: 416.401816284

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found in taxon: Acacia retinodes
chemical formula: C₂₉H₅₂O
canonical SMILES: CCC(CCC(C)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C)C(C)C
isomeric SMILES: CC[C@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@@H](C4)O)C)C)C(C)C
Commons category: Stigmastanol

Sources (3)

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Encyclopedic overview

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Contents

See also
References

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

Excerpted from Wikipedia’s “stigmastanol” article, available under the CC BY-SA 4.0 licence.

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