16-Oxo-26-hydroxycholesterol | 112347-32-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 16-Oxo-26-hydroxycholesterol
• 英文别名: 3β,27-dihydroxy-5-cholesten-16-one；26-hydroxycholesterol-16-one；(3S,8S,9S,10R,13S,14S,17R)-3-hydroxy-17-[(2R)-7-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,17-dodecahydrocyclopenta[a]phenanthren-16-one
• CAS: 112347-32-7
• 化学式: C₂₇H₄₄O₃
• 分子量: 416.645
• InChiKey: YEQXDBHOLDZYQY-JUJPKLCHSA-N

物化性质

• 熔点：
  170-171 °C
• 沸点：
  548.3±50.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  16-Oxo-26-hydroxycholesterol 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 、 肼 作用下， 以 1,4-二氧六环 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 26-(3-Methylindol-1-yl)cholesterol
  参考文献：
  名称：

  Synthesis of 26-halo-, 26-(phenylseleno)- and 26-indolyl cholesterol analogs

  摘要：

  DOI：

  10.1021/jo00327a025
• 作为产物：
  描述：

  薯蓣皂素 在 chromium(VI) oxide 、 盐酸 、 sodium acetate 、 汞 、 锌 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 18.25h， 生成 16-Oxo-26-hydroxycholesterol
  参考文献：
  名称：

  Synthesis of 26-halo-, 26-(phenylseleno)- and 26-indolyl cholesterol analogs

  摘要：

  DOI：

  10.1021/jo00327a025

文献信息

• Synthesis of potential C27-intermediates in bile acid biosynthesis and their deuterium-labeled analogs
  作者：Junichi Shoda、Magnus Axelson、Jan Sjövall

  DOI：10.1016/0039-128x(93)90048-r

  日期：1993.3

  In connection with studies of alternative pathways in bile acid biosynthesis, potential intermediates in a pathway starting with 27-hydroxylation of cholesterol have been prepared in natural and deuterated forms. Established methods were used to prepare 27-hydroxycholesterol and 3beta-hydroxy-5-cholestenoic acid. Clemmensen reduction of kryptogenin in unlabeled and deuterated solvents yielded 27-hydroxy-cholesterol and 16-oxo-5-cholestene-3beta,27-diol, which were separated by adsorption chromatography on Unisil. The labeled 27-hydroxycholesterol and 3beta-hydroxy-5-cholestenoic acid derived from it consisted of molecules with seven (50%), six (20%), and eight (20%) deuterium atoms, and unlabeled molecules were not detected. The acetates of 27-hydroxycholesterol and methyl 3beta-hydroxy-5-cholestenoate were 7alpha-hydroxylated in a copper-catalyzed reaction with tert-butylperbenzoate, and the products were purified by chromatography on Unisil. The 7beta-epimers were obtained as side products. Labeled 3beta,7alpha-dihydroxy-5-cholenoic acid was prepared in the same way from 3beta-hydroxy-5-[2,2,4,4,23-H-2(5)-cholenoic acid. The 3-oxo-DELTA4 analogs of the 3beta-hydroxy-DELTA5 compounds were prepared by oxidation with cholesterol oxidase. The labeled products had the same isotopic composition as the starting materials. Gas chromatographic retention indices and mass spectral characteristics of the trimethylsilyl ether derivatives of the neutral steroid and the methylated acids are given for all compounds.
• EP0258434A4
  申请人：——

  公开号：EP0258434A4

  公开（公告）日：1989-11-07
• COMPOSITION COMPRISING AN OXYGENATED CHOLESTEROL AND USE THEREOF FOR TOPICAL TREATMENT OF DISEASES
  申请人：JAVITT, Norman B.

  公开号：EP0258434A1

  公开（公告）日：1988-03-09
• CYTOSTATIC STEROLS
  申请人：MEDIVIR AB

  公开号：EP0906331A1

  公开（公告）日：1999-04-07
• US4743597A
  申请人：——

  公开号：US4743597A

  公开（公告）日：1988-05-10