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Stigmastanol

January 01, 1970

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
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
  • 83-45-4 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:89400
ChEMBL
  • ChEMBL252364
ChemSpider
  • 13078158
ECHA InfoCard 100.001.345
  • 15559396
UNII
  • C2NJ9WO6O7
  • 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 is the product of the reduction of β-sitosterol[5] and the hydrogenation of stigmasterol.[6]

See also edit

References edit

  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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January 01, 1970
stigmastanol, sitostanol, phytosterol, found, variety, plant, sources, similar, sterol, esters, stanol, esters, stigmastanol, inhibits, absorption, cholesterol, from, diet, animal, studies, suggest, that, also, inhibits, biosynthesis, cholesterol, liver, verif. 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 Names IUPAC name 5a Stigmastan 3b 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 3b Stigmastan 3 ol 3b 5a Stigmastan 3 ol b Sitostanol Dihydrositosterin Dihydrositosterol Dihydro b sitosterol Fucostanol Spinastanol 24a Ethylcholestanol Identifiers CAS Number 83 45 4 Y 3D model JSmol Interactive image ChEBI CHEBI 89400 ChEMBL ChEMBL252364 ChemSpider 13078158 ECHA InfoCard 100 001 345 PubChem CID 15559396 UNII C2NJ9WO6O7 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 formula C 29H 52O 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 Infobox references Stigmastanol is the product of the reduction of b sitosterol 5 and the hydrogenation of stigmasterol 6 See also editStigmasterol a closely related sterolReferences edit Sandqvist Hakan Bengtsson Edvard 1931 The empirical formula of sitosterol Berichte der Deutschen Chemischen Gesellschaft B 64 2167 2171 doi 10 1002 cber 19310640849 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 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 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 Thomasson Crompton David William Nickol Brent B 1985 Biology of the Acanthocephala Cambridge University Press p 185 ISBN 9780521246743 Paxena P B 2007 Chemistry of Alkaloids Discovery Publishing Hous p 231 ISBN 9788183563161 nbsp This article about a steroid is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Stigmastanol amp oldid 1153574395, wikipedia, wiki, book, books, library,

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