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Stigmastanol

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.345 Edit this at Wikidata
UNII
  • 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/s1
    Key: LGJMUZUPVCAVPU-KZXGMYDKSA-N
  • 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
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).

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 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 B. 64: 2167–2171. doi:10.1002/cber.19310640849.
  2. ^ a b 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. PMID 16483871.
  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 GA, 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. S2CID 23279253.
  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.


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