豆甾烷醇

豆甾烷醇(英語:Stigmastanol,或称为谷甾烷醇sitostanol豆甾烷-3β-醇,Stigmastan-3β-ol)是一种存在于许多植物中的植物固醇,这一类的化合物能抑制人体对食物中胆固醇的吸收[1][2][3]。动物实验表明豆甾烷醇还能抑制肝脏胆固醇的合成[1]

豆甾烷醇
IUPAC名
(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
系统名
(1S,2S,5S,7S,10R,11S,14R,15R)-14-[(1R,4R)-4-ethyl-1,5-dimethylhexyl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-5-ol

(1S,2S,5S,7S,10R,11S,14R,15R)-2,15-二甲基-14-[(1R,4R)-1,5-二甲基-4-乙基己基]四环[8.7.0.02,7.011,15]-5-十七醇

别名 (3β)-Stigmastan-3-ol; (3β,5α)-Stigmastan-3-ol; β-Sitostanol; Dihydrositosterin; Dihydrositosterol; Dihydro-β-sitosterol; Fucostanol; Spinastanol; 24α-Ethylcholestanol
识别
CAS号 83-45-4  checkY
PubChem 241572
ChemSpider 13078158
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
ChEBI 89400
性质
化学式 C29H52O
摩尔质量 416.72 g·mol−1
沸点 139.4 - 139.8 °C(273 K)
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

豆甾烷醇可看作豆固醇β-谷固醇氢化产物[4][5]

参考文献

  1. ^ 1.0 1.1 Batta, Ashok K.; Xu, Guorong; Honda, Akira; Miyazaki, Teruo; Salen, Gerald. Stigmasterol reduces plasma cholesterol levels and inhibits hepatic synthesis and intestinal absorption in the rat. Metabolism, Clinical and Experimental. 2006, 55 (3): 292–299. doi:10.1016/j.metabol.2005.08.024. 
  2. ^ Heinemann T, Pietruck B, Kullak-Ublick G, von Bergmann K. Comparison of sitosterol and sitostanol on inhibition of intestinal cholesterol absorption. Agents and Actions. Supplements  . 1988, 26: 117–122. PMID 3265272. 
  3. ^ Heinemann T, Kullak-Ublick GA, Pietruck B, von Bergmann K. Mechanisms of action of plant sterols on inhibition of cholesterol absorption. Comparison of sitosterol and sitostanol. European Journal of Clinical Pharmacology  . 1991, 40 (Suppl 1): S59–63. PMID 2044646. doi:10.1007/BF01409411. 
  4. ^ Thomasson Crompton, David William; Nickol, Brent B. Biology of the Acanthocephala. Cambridge University Press. 1985: 185 [2019-10-15]. ISBN 9780521246743. (原始内容存档于2016-04-11). 
  5. ^ Paxena, P. B. Chemistry of Alkaloids. Discovery Publishing Hous. 2007: 231 [2019-10-15]. ISBN 9788183563161. (原始内容存档于2016-04-12).