3-氧代-7-羟基胆-4-烯酸 | 14772-95-3

• 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-7-羟基胆-4-烯酸
• 英文名称: 7α-hydroxy-3-oxochol-4-en-24-oic acid
• 英文别名: 3-oxo-7α-hydroxy-4-cholenic acid；7alpha-Hydroxy-3-oxochol-4-en-24-oic acid；(4R)-4-[(7R,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
• CAS: 14772-95-3
• 化学式: C₂₄H₃₆O₄
• 分子量: 388.547
• InChiKey: CFLVYJJIZHNITM-NLXMLWGDSA-N

物化性质

• 熔点：
  231-233 °C
• 沸点：
  565.9±33.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

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

安全信息

• 储存条件：
  室温

制备方法与用途

3-氧代-7-羟基胆-4-烯酸是一种内源性代谢产物，可能作为肝胆疾病预后不良的重要指标。

反应信息

• 作为反应物：
  描述：

  3-氧代-7-羟基胆-4-烯酸 在 氨 、 lithium 作用下， 以 吡啶 为溶剂， 生成 methyl 3β-cathyloxy-7α-mesyloxy-5α-cholanate
  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：
• 作为产物：
  描述：

  3β,7α-dihydroxy-5-cholen-24-oic acid 在 phosphate buffer pH 7.0 、 cholesterol oxidase 作用下， 以 水 、 异丙醇 为溶剂， 反应 3.0h， 生成 3-氧代-7-羟基胆-4-烯酸
  参考文献：
  名称：

  Synthesis of potential C27-intermediates in bile acid biosynthesis and their deuterium-labeled analogs

  摘要：

  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.

  DOI：

  10.1016/0039-128x(93)90048-r

文献信息

• Methods for diagnosing motor neuron diseases
  申请人：SWANSEA UNIVERSITY

  公开号：US11536730B2

  公开（公告）日：2022-12-27

  The invention relates to methods for determining whether a subject is afflicted with a motor neuron disease, the method comprising conducting an analysis of cerebrospinal fluid and/or plasma, measuring the level of one or more sterol/oxysterol analytes, and comparing these to reference values. Further, the invention relates to methods of identifying agents suitable for the treatment of MND, and monitoring the progress of the disease.

  本发明涉及确定受试者是否患有运动神经元疾病的方法，该方法包括对脑脊液和/或血浆进行分析，测量一种或多种甾醇/氧甾醇分析物的水平，并将其与参考值进行比较。 此外，本发明还涉及鉴定适用于治疗运动神经元疾病的药物和监测疾病进展的方法。
• 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
• COMPOUND AND METHOD FOR THE TREATMENT OF NEURODEGENERATIVE CONDITIONS
  申请人：Swansea University

  公开号：EP2961400B1

  公开（公告）日：2017-11-01
• METHODS FOR DIAGNOSING MOTOR NEURON DISEASES
  申请人：SWANSEA UNIVERSITY

  公开号：US20190310267A1

  公开（公告）日：2019-10-10

  The invention relates to methods for determining whether a subject is afflicted with a motor neuron disease, the method comprising conducting an analysis of cerebrospinal fluid and/or plasma, measuring the level of one or more sterol/oxysterol analytes, and comparing these to reference values. Further, the invention relates to methods of identifying agents suitable for the treatment of MND, and monitoring the progress of the disease.