(3alpha,5beta,7alpha)-7-羟基-3-(磺基氧基)胆烷-24-酸 | 59132-32-0

• 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
• 中文名称: (3alpha,5beta,7alpha)-7-羟基-3-(磺基氧基)胆烷-24-酸
• 英文名称: 7-hydroxy-3-(sulfooxy)-(3α,5β,7α)-cholan-24-oic acid
• 英文别名: chenodeoxycholic acid 3-sulfate；3-sulfochenodeoxycholic acid；chenodeoxycholic acid 3-O-sulfate；CDCA-3S；(4R)-4-[(3R,5R,7R,8R,9S,10S,13R,14S,17R)-7-hydroxy-10,13-dimethyl-3-sulfooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 59132-32-0
• 化学式: C₂₄H₄₀O₇S
• 分子量: 472.643
• InChiKey: WHMOBEGYTDWMIG-BSWAIDMHSA-N

物化性质

• 物理描述：
  Solid
• 碰撞截面：
  194.9 Ų [M-H]- [CCS Type: DT, Method: single field calibrated]

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  7

制备方法与用途

鹅去氧胆酸3-硫酸盐是一种胆汁酸，其水平与肝功能障碍的程度密切相关。

反应信息

• 作为反应物：
  描述：

  (3alpha,5beta,7alpha)-7-羟基-3-(磺基氧基)胆烷-24-酸 在 盐酸 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 18.0h， 生成 鹅去氧胆酸
  参考文献：
  名称：

  Solvolysis of chenodeoxycholic acid sulfates

  摘要：

  Chemical solvolysis of chenodeoxycholic acid sulfates was studied using 4 published methods. Quantitative recovery of chenodeoxycholic acid from the 3-sulfate was obtained with each method. However, only 2 methods yielded chenodeoxycholic acid after solvolysis of the 7-sulfate. In each instance a compound resembling lithocholic acid by GLC but identifiable as a derivative of chenodeoxycholic acid by mass spectrometry was obtained and represents a product formed during solvolysis. Failure to obtain adequate solvolysis of chenodeoxycholic acid 7-sulfate can lead to false identification of monohydroxy bile acids and apparent absence of th 7-sulfate and disulfate esters.

  DOI：

  10.1016/s0039-128x(81)90149-5
• 作为产物：
  描述：

  鹅去氧胆酸 在 吡啶 、 三氧化硫吡啶 作用下， 反应 0.17h， 生成 (3alpha,5beta,7alpha)-7-羟基-3-(磺基氧基)胆烷-24-酸
  参考文献：
  名称：

  Bandiera, Tiziano; Albini, Franca Marione; Albini, Enrico, Synthetic Communications, 1987, vol. 17, # 9, p. 1111 - 1118

  摘要：

  DOI：

文献信息

• Scroll composite having amphiphilic substance inside and method for preparation of the same
  申请人：INDUSTRY-UNIVERSITY COOPERATION FOUNDATION HANYANG UNIVERSITY

  公开号：US11247904B2

  公开（公告）日：2022-02-15

  Provided are a scroll preparing method using a two-dimensional material and a scroll prepared thereby. The scroll preparing method comprises preparing a two-dimensional material. The two-dimensional material is scrolled by providing an amphiphilic substance having a hydrophilic portion and a hydrophobic portion on the two-dimensional material. As a result, a scroll composite including the amphiphilic substance disposed inside a scroll structure is formed.

  本文提供了一种使用二维材料制备卷轴的方法以及由此制备的卷轴。卷轴制备方法包括制备二维材料。通过在二维材料上提供具有亲水部分和疏水部分的两亲物质，将二维材料制成卷轴。这样就形成了一种卷轴复合材料，其中包括置于卷轴结构内部的亲水性物质。
• The synthesis of taurine-conjugated bile acids and bile acid sulfates labeled with 14C or 3H in the taurine moiety
  作者：Jie Zhang、William J. Griffiths、Jan Sjövall

  DOI：10.1002/(sici)1099-1344(199702)39:2<159::aid-jlcr954>3.0.co;2-w

  日期：1997.2
• Synthesis of the 3-sulfates of S-acyl glutathione conjugated bile acids and their biotransformation by a rat liver cytosolic fraction
  作者：Kuniko Mitamura、Naohiro Hori、Shiori Mino、Takashi Iida、Alan F. Hofmann、Shigeo Ikegawa

  DOI：10.1016/j.chemphyslip.2012.02.001

  日期：2012.4

  The 3-sulfates of the S-acyl glutathione (GSH) conjugates of five natural bile acids (cholic, chenodeoxycholic, deoxycholic, ursodeoxycholic, and lithocholic) were synthesized as reference standards in order to investigate their possible formation by a rat liver cytosolic fraction. Their structures were confirmed by proton nuclear magnetic resonance, as well as by means of electrospray ionization-linear ion-trap mass spectrometry with negative-ion detection. Upon collision-induced dissociation, structurally informative product ions were observed. Using a triple-stage quadrupole instrument, selected reaction monitoring analyses by monitoring characteristic transition ions allowed the achievement of a highly sensitive and specific assay. This method was used to determine whether the 3-sulfates of the bile acid-GSH conjugates (BA-GSH) were formed when BA-GSH were incubated with a rat liver cytosolic fraction to which 3'-phosphoadenosine 5'-phosphosulfate had been added. The S-acyl linkage was rapidly hydrolyzed to form the unconjugated bile acid. A little sulfation of the GSH conjugates occurred, but greater sulfation at C-3 of the liberated bile acid occurred. Sulfation was proportional to the hydrophobicity of the unconjugated bile acid. Thus GSH conjugates of bile acids as well as their C-3 sulfates if formed in vivo are rapidly hydrolyzed by cytosolic enzymes. (C) 2012 Elsevier Ireland Ltd. All rights reserved.
• SCROLL COMPOSITE HAVING AMPHIPHILIC SUBSTANCE INSIDE AND METHOD FOR PREPARATION OF THE SAME
  申请人：INDUSTRY-UNIVERSITY COOPERATION FOUNDATION HANYANG UNIVERSITY

  公开号：US20160355401A1

  公开（公告）日：2016-12-08

  Provided are a scroll preparing method using a two-dimensional material and a scroll prepared thereby. The scroll preparing method comprises preparing a two-dimensional material. The two-dimensional material is scrolled by providing an amphiphilic substance having a hydrophilic portion and a hydrophobic portion on the two-dimensional material. As a result, a scroll composite including the amphiphilic substance disposed inside a scroll structure is formed.