光甾醇

光甾醇英語:,又叫光固醇,(3b,9b,10a,22E)-Ergosta-5,7,22-trien-3-ol)是一种分子式C28H44O类固醇化合物,是麦角固醇的(9β,10α)立体异构[2]。过去的维生素D1实际上是维生素D2和光甾醇的混合物,光甾醇可通过σ[1,7]迁移反应转化为维生素D2[3]

Lumisterol
IUPAC名
(3S,9R,10S,13R,14R,17R)-17-[(E,2R,5R)-5,6-Dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
识别
CAS号 474-69-1  checkY
PubChem 6436872
ChemSpider 4941479
SMILES
 
  • O[C@@H]4C/C3=C/C=C1\[C@@H](CC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@H](C)C(C)C)C)C)[C@]3(C)CC4
InChI
 
  • 1/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26+,27+,28+/m0/s1
InChIKey DNVPQKQSNYMLRS-YAPGYIAOBK
性质
化学式 C28H44O
摩尔质量 396.65 g·mol−1
熔点 118 °C(391 K)[1]
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

光甾醇还有一种与7-脱氢胆固醇相似的类似物,称为光甾醇3[4]

转化为维生素D2

参考文献

  1. A. Windaus, K. Dithmar, E. Fernholz. . Justus Liebig's Annalen der Chemie. 1932, 493 (1): 259–271 [2020-01-18]. doi:10.1002/jlac.19324930117 (德语).
  2. Dewick, Paul M. (PDF) Second. New York: John Wiley & Sons. 2002: 259 [2020-01-01]. ISBN 0-471-49640-5. (原始内容存档 (PDF)于2018-02-19).
  3. Friedmann, Ernst. Neurath, Hans , 编. . Perspectives in Biochemistry. Volume 1. Washington, DC: American Chemical Society. 1989 [2020-01-01]. ISBN 978-0-8412-1621-1. (原始内容存档于2014-01-03).
  4. National Center for Biotechnology Information. . PubChem Compound Database. [10 April 2018]. (原始内容存档于2020-01-01) (英语).


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