3-氧代胆a-4,6-二烯-24-酸 | 88179-71-9

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: 3-氧代胆a-4,6-二烯-24-酸
• 中文别名: 2-溴-N-(4-{2-[(2R,6R,11R)-8-羟基-6,11-二甲基-1,4,5,6-四氢-2,6-亚甲基-3-苯并吖辛因-3(2H)-基]乙基}苯基)乙酰胺
• 英文名称: 3-Oxochola-4,6-dien-24-oic acid
• 英文别名: 3-oxo-4,6-choladienoic acid；3-oxo-4,6-choladienic acid；cholan-4,6-dien-3-one-24-oic acid；(4R)-4-[(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-oxo-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 88179-71-9
• 化学式: C₂₄H₃₄O₃
• 分子量: 370.532
• InChiKey: CREVIXFSUWYGRJ-IHMUCKAYSA-N

物化性质

• 沸点：
  541.8±19.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

制备方法与用途

3-氧代-4,6-胆红素-24-油酸是人体的一种内源性代谢产物。在肝胆疾病的患者尿液中可以检测到这种物质。

反应信息

• 作为反应物：
  描述：

  3-氧代胆a-4,6-二烯-24-酸 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以99%的产率得到methyl 3-oxochola-4,6-dien-24-oate
  参考文献：
  名称：

  EP1985621

  摘要：

  公开号：
• 作为产物：
  描述：

  7β-formyloxy-3-oxo-5β-cholanoic acid-(24) 在 sodium acetate 、 丙酮酸 、 S-(4-叔-丁基苯甲基)[2-(1-甲基丁基)吡啶-3-基]硫代氨基甲酸酯 作用下， 反应 1.5h， 生成 3-氧代胆a-4,6-二烯-24-酸
  参考文献：
  名称：

  Iida, Takashi; Momose, Toshiaki; Nambara, Toshio, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 5, p. 1929 - 1933

  摘要：

  DOI：

文献信息

• METHOD FOR PRODUCING STEROID COMPOUND
  申请人：Takehara Jun

  公开号：US20100063272A1

  公开（公告）日：2010-03-11

  It is an object of the present invention to provide a novel method for producing a steroid compound. The present invention provides a method for producing 5β-3,7-dioxocholanic acid or an ester derivative thereof, using, as a raw material, a sterol having double bonds at position 5 and at position 24, such as cholesta-5,7,24-trien-3β-ol, ergosta-5,7,24(28)-trien-3β-ol, desmosterol, fucosterol, or ergosta-5,24(28)-dien-3β-ol, via the following 4 steps: (I) a step involving oxidation of a hydroxyl group at position 3 and isomerization of a double bond at position 5 to position 4; (II) a step involving the oxidative cleavage of a side chain to convert position 24 to a carboxyl group or an ester derivative thereof; (III) a step of introducing an oxygen functional group into position 7; and (IV) a step of constructing a 5β configuration by reductive saturation of a double bond at position 4.

  本发明的目的是提供一种新型类固醇化合物的制备方法。本发明提供了一种以具有5号和24号位置双键的类固醇（如胆甾-5,7,24-三烯-3β-醇、麦角甾-5,7,24(28)-三烯-3β-醇、脱甾醇、褐藻甾醇或麦角甾-5,24(28)-二烯-3β-醇）为原料，通过以下4个步骤制备5β-3,7-二氧代胆甾酸或其酯衍生物：(I) 氧化3号羟基并异构化5号双键至4号的步骤；(II) 氧化断裂侧链以将24号位置转化为羧基或其酯衍生物的步骤；(III) 在7号位置引入氧功能团的步骤；和(IV) 通过还原饱和4号位置的双键构建5β构型的步骤。
• PROCESS FOR PRODUCTION OF STEROIDS
  申请人：Mitsubishi Chemical Corporation

  公开号：EP1985621A1

  公开（公告）日：2008-10-29

  It is an object of the present invention to provide a novel method for producing a steroid compound. The present invention provides a method for producing 5β-3,7-dioxocholanic acid or an ester derivative thereof, using, as a raw material, a sterol having double bonds at position 5 and at position 24, such as cholesta-5,7,24-trien-3β-ol, ergosta-5,7,24(28)-trien-3β-ol, desmosterol, fucosterol, or ergosta-5,24(28)-dien-3β-ol, via the following 4 steps: (I) a step involving oxidation of a hydroxyl group at position 3 and isomerization of a double bond at position 5 to position 4; (II) a step involving the oxidative cleavage of a side chain to convert position 24 to a carboxyl group or an ester derivative thereof; (III) a step of introducing an oxygen functional group into position 7; and (IV) a step of constructing a 5β configuration by reductive saturation of a double bond at position 4.

  本发明的目的是提供一种生产类固醇化合物的新方法。本发明提供了一种生产 5β-3,7-二氧代胆烷酸或其酯类衍生物的方法，该方法以位置 5 和位置 24 具有双键的甾醇为原料，例如胆甾-5,7,24-三烯-3β-醇、麦角甾-5,7,24(28)-三烯-3β-醇、去甲胆甾醇、褐藻甾醇或麦角甾-5,24(28)-二烯-3β-醇，通过以下 4 个步骤进行生产： (I) 氧化位置 3 的羟基，并将位置 5 的双键异构化为位置 4； (II) 氧化裂解侧链，将位置 24 转化为羧基或其酯衍生物的步骤 (III) 将氧官能团引入位置 7 的步骤；以及 (IV) 通过还原饱和位置 4 的双键来构建 5β 构型的步骤。
• Therapeutic stem cell growth factor composition, anti-inflammatory composition, and uses thereof
  申请人：Girsh S. Leonard

  公开号：US20060074051A1

  公开（公告）日：2006-04-06

  The present invention relates to a composition and uses thereof for treatment of damaged tissue comprising at least one essential amino acid in L form and at least one essential lipid; wherein the composition is administered to a mammal suffering from severe tissue damage. The invention further relates to a composition and uses thereof comprising a mixture of one or more free L-amino acids in which the molar ratio of the free L-amino acids corresponds to the molar ratio of amino components in a mammalian tissue protein; and at least one essential lipid.

  本发明涉及一种用于治疗受损组织的组合物及其用途，该组合物包含至少一种L形式的必需氨基酸和至少一种必需脂质；其中该组合物被施用给遭受严重组织损伤的哺乳动物。本发明还涉及一种组合物及其用途，该组合物包含一种或多种游离 L-氨基酸的混合物，其中游离 L-氨基酸的摩尔比与哺乳动物组织蛋白质中氨基酸成分的摩尔比一致；以及至少一种必需脂质。
• 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.
• KIT AND METHOD FOR QUANTITATIVE DETECTION OF STEROIDS
  申请人：Swansea University

  公开号：EP2893355B1

  公开（公告）日：2019-06-05