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
83-45-4 Yes
ChEMBL ChEMBL252364
ChemSpider 13078158
Jmol-3D images Image
PubChem 15559396
UNII C2NJ9WO6O7
Properties
Molecular formula
 C29H52O
Molar mass 416.72 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 noted otherwise, data is 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.[2][3][4] Animal studies suggest that it also inhibits biosynthesis of cholesterol in the liver.[2]

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

See also

References

  1. ↑ Sandqvist, Hakan; Bengtsson, Edvard (1931). "The empirical formula of sitosterol". Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen 64B: 2167–2171.
  2. ↑ 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. doi:10.1016/j.metabol.2005.08.024.
  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.
  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.
  5. ↑ Thomasson Crompton, David William; Nickol, Brent B. (1985). Biology of the Acanthocephala. Cambridge University Press. p. 185. ISBN 9780521246743.
  6. ↑ Paxena, P. B. (2007). Chemistry of Alkaloids. Discovery Publishing Hous. p. 231. ISBN 9788183563161.