3α,6α-dihydroxy-7-oxo-5β-cholan-24-oic acid | 88725-42-2

• 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: 3α,6α-dihydroxy-7-oxo-5β-cholan-24-oic acid
• 英文别名: takeda ketol；7-oxohyodeoxycholic acid；3α,6α-Dihydroxy-7-oxo-5β-cholan-24-saeure；3alpha,6alpha-Dihydroxy-7-oxo-5beta-cholan-24-oic Acid；(4R)-4-[(3R,5R,6R,8S,9S,10R,13R,14S,17R)-3,6-dihydroxy-10,13-dimethyl-7-oxo-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 88725-42-2
• 化学式: C₂₄H₃₈O₅
• 分子量: 406.563
• InChiKey: NYMYNCFPAHUJJK-XBTSAHOMSA-N

物化性质

• 熔点：
  184-186 °C
• 沸点：
  583.0±45.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3α,6α-dihydroxy-7-oxo-5β-cholan-24-oic acid 在 chromium(VI) oxide 、 甲醇 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 生成 3-oxo-6,7-seco-5β-cholane-6,7,24-trioic acid
  参考文献：
  名称：

  Hsia et al., Journal of Biological Chemistry, 1957, vol. 225, p. 811,818

  摘要：

  DOI：
• 作为产物：
  描述：

  sodium cholate 在 Pseudomonas fluorescens BS₇ broth 作用下， 以 水 为溶剂， 反应 48.0h， 以96%的产率得到3α,6α-dihydroxy-7-oxo-5β-cholan-24-oic acid
  参考文献：
  名称：

  Regioselective microbial oxidation of bile acids

  摘要：

  High regioselectivity in the microbial oxidation of C-7, C-3 and C-12 hydroxyl groups of cholic, chenodeoxycholic, deoxycholic and hyocholic acids 1-4 is reported. The tested microrganisms have been isolated from 50 enviromental samples withdrawed from an industry that extracts and purify bile acids. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10408-2

文献信息

• Synthesis of ω‐Muricholic Acid by One‐Pot Enzymatic Mitsunobu Inversion using Hydroxysteroid Dehydrogenases
  作者：Susanna Bertuletti、Erica Elisa Ferrandi、Daniela Monti、Giovanni Fronza、Ivan Bassanini、Sergio Riva

  DOI：10.1002/cctc.202101307

  日期：2021.12.7

  One-pot reaction: ω-Muricholic acid was obtained from its 7α-epimer hyocholic acid via 7α- and 7β-HSDH-mediated one-pot redox biotransformations.

  一锅反应：通过 7α- 和 7β-HSDH 介导的一锅氧化还原生物转化，从其 7α-差向异构体胆酸中获得 ω-鼠胆酸。
• THE STRUCTURE OF HYOCHOLIC ACID
  作者：P. Ziegler

  DOI：10.1139/v56-199

  日期：1956.11.1

  Further evidence for the α-configuration of the hydroxyl groups in hyocholic acid is presented and several related compounds are described.

  进一步提供了乾胆酸中羟基团的α-构型的证据，并描述了几个相关化合物。
• Enzymatic .alpha./.beta. inversion of the C-7-hydroxyl of steroids
  作者：Roberto Bovara、Enrica Canzi、Giacomo Carrea、Alessandra Pilotti、Sergio Riva

  DOI：10.1021/jo00054a039

  日期：1993.1
• 7α-OH epimerisation of bile acids via oxido-reduction with Xanthomonas maltophilia
  作者：Alessandro Medici、Paola Pedrini、Ercolina Bianchini、Giancarlo Fantin、Alessandra Guerrini、Benedetto Natalini、Roberto Pellicciari

  DOI：10.1016/s0039-128x(01)00136-2

  日期：2002.1

  The microbial 7 alpha -OH epimerisation of cholic, chenodeoxycholic, and 12-ketochenodeoxycholic acids (7 alpha -OH bile acids) with Xanthomonas maltophilia CBS 827.97 to corresponding 7 beta -OH derivatives with scarcity of oxygen is described. With normal pressure of oxygen the 7-OH oxidation products are obtained. No biotransformations are achieved in anaerobic conditions. The microbial 7 alpha -OH epimerisation is achieved by oxidation of 7-OH function and subsequent reduction. Partial purification, in fact, of the enzymatic fraction revealed the presence of two hydroxysteroid dehydrogenases (HSDH) alpha- and beta -stereospecific together with a glycocholate hydrolase. On the basis of these results a further application is the microbial reduction of 6 alpha -fluoro and 6 beta -fluoro-3 alpha -hydroxy-7-oxo-5 beta -cholan-24-oic acid methyl esters to the corresponding 7 alpha -OH and 7 beta -OH derivatives. (C) 2002 Elsevier Science Inc. All rights reserved.
• [EN] SYNTHETIC DERIVATIVES OF CHOLIC ACID 7-SULFATE AND USES THEREOF<br/>[FR] DÉRIVÉS SYNTHÉTIQUES DU 7-SULFATE D'ACIDE CHOLIQUE ET UTILISATIONS DE CEUX-CI
  申请人：HARVARD COLLEGE

  公开号：WO2020117945A8

  公开（公告）日：2020-07-02