Stigmastanol
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| Stigmastanol | |
|---|---|
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| 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  |
| PubChem | 15559396 |
| ChemSpider | 13078158 |
| UNII | C2NJ9WO6O7 |
| ChEMBL | CHEMBL252364 |
| Jmol-3D images | {{#if: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|Image 1 |
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| Properties | |
| Molecular formula | C29H52O |
| Molar mass | 416.72 g mol−1 |
| Boiling point | 139.4–139.8 °C[1] |
| Except where noted otherwise, 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]
See also
- Stigmasterol, a closely related sterol
References
- ↑ Sandqvist, Hakan; Bengtsson, Edvard (1931). "The empirical formula of sitosterol". Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen 64B: 2167–2171.
- ↑ 2.0 2.1 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.
- ↑ 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 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.
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