7β-hydroxy-3-oxochol-4-en-24-oic acid

• 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: 7β-hydroxy-3-oxochol-4-en-24-oic acid
• 英文别名: KCEA；(4R)-4-[(7S,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
• 化学式: C₂₄H₃₆O₄
• 分子量: 388.547
• InChiKey: CFLVYJJIZHNITM-HRZOSYEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7β-hydroxy-3-oxochol-4-en-24-oic acid 在 platinum(IV) oxide 、 重铬酸吡啶 、 N-羟基邻苯二甲酰亚胺 、 水 、 氢气 、 对甲苯磺酸 、 溶剂黄146 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 异丙醇 、 甲苯 、 乙腈 为溶剂， -78.0~100.0 ℃ 、68.95 kPa 条件下， 反应 20.25h， 生成 3α-羟基-7-氧代-胆烷酸-24-甲酯
  参考文献：
  名称：

  METHODS OF MAKING CHOLIC ACID DERIVATIVES AND STARTING MATERIALS THEREFOR

  摘要：

  制备胆酸衍生物的方法，特别是优瑟酸、牛磺基优瑟酸、7-酮石胆酸、奥贝替酸，它们的羧酸盐和羧酸酯，以及相应的起始物和中间体。

  公开号：

  US20220056070A1
• 作为产物：
  描述：

  熊去氧胆酸 以 水 为溶剂， 反应 120.0h， 以32%的产率得到3α-methoxy-7β-hydroxy-5β-cholanoic acid
  参考文献：
  名称：

  Bile acid transformations by Alcaligenes recti

  摘要：

  Metabolism of cholic acid, chenodeoxycholic acid, ursodeoxycholic acid, and deoxycholic acid by the grown cells of the bacterium Alcaligenes recti suspended in water was studied. Each isolated metabolite was characterized by the application of various spectroscopic methods. Cholic acid, chenodeoxycholic acid, ursodeoxycholic acid, and deoxycholic acid yielded methylated derivatives 3alpha-methoxy-7alpha, 12alpha-dihydroxy-5beta-cholanoic acid, 3alpha-methoxy-7alpha-hydroxy-5beta-cholanoic acid, 3alpha-methoxy-7beta-hydroxy-5beta-cholanoic acid, and 3alpha-methoxy-12alpha-hydroxy-5beta-cholanoic acid, respectively. In addition, cholic acid furnished 7alpha,12alpha-dihydroxy-3-oxochol-4-en-24-oic acid; chenodeoxycholic acid gave 7alpha-hydroxy-3-oxo-5beta-cholanoic acid and 7alpha-hydroxy-3-oxochol-4-en-24-oic acid while ursodeoxycholic acid yielded 7beta-hydroxy-3-oxochol-4-en-24-oic acid and 3-oxochola-4,6-dien-24-oic acid. The formation of various metabolites showed that two competitive enzymic reactions, i.e., selective methylation of the 3alpha-hydroxy group and dehydrogenation in the A/B rings, were operative. The methylation process was found to be enzymic involving an S-adenosyl-L-methionine (AdoMet)-dependent methyl transferase, and this reaction appeared to be inhibitory to the process of degradation of the ring system. In the other reaction sequence, degradation of the ring system was initiated by dehydrogenation of the 3alpha-hydroxy group. A 7beta-dehydratase activity producing the DELTA6 double bond was also noticeable in the metabolism of ursodeoxycholic acid.

  DOI：

  10.1016/0039-128x(93)90057-t

文献信息

• Bile acid transformations by Alcaligenes recti
  作者：Ipsita Mazumder、Shashi B. Mahato

  DOI：10.1016/0039-128x(93)90057-t

  日期：1993.2

  Metabolism of cholic acid, chenodeoxycholic acid, ursodeoxycholic acid, and deoxycholic acid by the grown cells of the bacterium Alcaligenes recti suspended in water was studied. Each isolated metabolite was characterized by the application of various spectroscopic methods. Cholic acid, chenodeoxycholic acid, ursodeoxycholic acid, and deoxycholic acid yielded methylated derivatives 3alpha-methoxy-7alpha, 12alpha-dihydroxy-5beta-cholanoic acid, 3alpha-methoxy-7alpha-hydroxy-5beta-cholanoic acid, 3alpha-methoxy-7beta-hydroxy-5beta-cholanoic acid, and 3alpha-methoxy-12alpha-hydroxy-5beta-cholanoic acid, respectively. In addition, cholic acid furnished 7alpha,12alpha-dihydroxy-3-oxochol-4-en-24-oic acid; chenodeoxycholic acid gave 7alpha-hydroxy-3-oxo-5beta-cholanoic acid and 7alpha-hydroxy-3-oxochol-4-en-24-oic acid while ursodeoxycholic acid yielded 7beta-hydroxy-3-oxochol-4-en-24-oic acid and 3-oxochola-4,6-dien-24-oic acid. The formation of various metabolites showed that two competitive enzymic reactions, i.e., selective methylation of the 3alpha-hydroxy group and dehydrogenation in the A/B rings, were operative. The methylation process was found to be enzymic involving an S-adenosyl-L-methionine (AdoMet)-dependent methyl transferase, and this reaction appeared to be inhibitory to the process of degradation of the ring system. In the other reaction sequence, degradation of the ring system was initiated by dehydrogenation of the 3alpha-hydroxy group. A 7beta-dehydratase activity producing the DELTA6 double bond was also noticeable in the metabolism of ursodeoxycholic acid.
• METHODS OF MAKING CHOLIC ACID DERIVATIVES AND STARTING MATERIALS THEREFOR
  申请人：Sandhill One, LLC

  公开号：US20220056070A1

  公开（公告）日：2022-02-24

  Methods of making cholic acid derivatives, particularly ursodeoxycholic acid, tauroursodeoxycholic acid, 7-ketolithocholic acid, obeticholic acid, their carboxylate salts and carboxylate esters, and starting materials and intermediates therefor.

  制备胆酸衍生物的方法，特别是优瑟酸、牛磺基优瑟酸、7-酮石胆酸、奥贝替酸，它们的羧酸盐和羧酸酯，以及相应的起始物和中间体。