4-Isopropenyl-cyclohexanecarboxylic acid | 134955-99-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-Isopropenyl-cyclohexanecarboxylic acid
• CAS: 134955-99-0
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: XZOBEDLKVOHSSH-KYZUINATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-Isopropenyl-cyclohexanecarboxylic acid 在 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Structure determination of metabolites isolated from urine and bile after administration of AY4166, a novel d-phenylalanine-derivative hypoglycemic agent

  摘要：

  Molecular structures of 10 metabolites, which were isolated from urine (M1-M8) or bile (M9 and MIG) after administration of AY4166 (N-(trans-4-isopropylcyclohexanecarbonyl)-D-phenylalanine), a novel amino acid derivative with hypoglycemic activity, have been elucidated by mass spectrometry and nuclear magnetic resonance. Four of these (M1, M2, M3 and M8) were determined to be hydroxyl derivatives of AY4166, two (M9 and M10) were carboxylate derivatives via oxidization of M2 and M3, three (M4, M5 and M6) were glucronic acid conjugates and the other (M7) was a dehydro derivative. The estimated structures for M1, M2, M3, M7, Ms, M9 and MIO were confirmed by the coincidence of the retention time of HPLC, MS and H-1 NMR spectra between the isolated metabolites and authentic synthesized substances. For three glucronic acid conjugates, M4, M5 and M6, structural confirmation was performed by a selective enzymatic digestion with beta-glucronidase. M1 and M2/3 were about 5-6 and 3 times less potent than AY4166, respectively, and M7 was almost as potent as AY4166. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00187-3
• 作为产物：
  描述：

  Trans-1,4-Cyclohexanedicarboxylic Acid Monomethyl Ester 在 sodium hydroxide 、 copper(l) iodide 、 氯化亚砜 、 四氯化钛 、 锌 作用下， 以 甲醇 为溶剂， 反应 13.0h， 生成 4-Isopropenyl-cyclohexanecarboxylic acid
  参考文献：
  名称：

  Structure determination of metabolites isolated from urine and bile after administration of AY4166, a novel d-phenylalanine-derivative hypoglycemic agent

  摘要：

  Molecular structures of 10 metabolites, which were isolated from urine (M1-M8) or bile (M9 and MIG) after administration of AY4166 (N-(trans-4-isopropylcyclohexanecarbonyl)-D-phenylalanine), a novel amino acid derivative with hypoglycemic activity, have been elucidated by mass spectrometry and nuclear magnetic resonance. Four of these (M1, M2, M3 and M8) were determined to be hydroxyl derivatives of AY4166, two (M9 and M10) were carboxylate derivatives via oxidization of M2 and M3, three (M4, M5 and M6) were glucronic acid conjugates and the other (M7) was a dehydro derivative. The estimated structures for M1, M2, M3, M7, Ms, M9 and MIO were confirmed by the coincidence of the retention time of HPLC, MS and H-1 NMR spectra between the isolated metabolites and authentic synthesized substances. For three glucronic acid conjugates, M4, M5 and M6, structural confirmation was performed by a selective enzymatic digestion with beta-glucronidase. M1 and M2/3 were about 5-6 and 3 times less potent than AY4166, respectively, and M7 was almost as potent as AY4166. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00187-3

文献信息

• Structure determination of metabolites isolated from urine and bile after administration of AY4166, a novel d-phenylalanine-derivative hypoglycemic agent
  作者：Hiroko Takesada、Keizo Matsuda、Ryoko Ohtake、Ryuichi Mihara、Ichiro Ono、Kenzo Tanaka、Masaki Naito、Masanobu Yatagai、Ei-ichiro Suzuki

  DOI：10.1016/0968-0896(96)00187-3

  日期：1996.10

  Molecular structures of 10 metabolites, which were isolated from urine (M1-M8) or bile (M9 and MIG) after administration of AY4166 (N-(trans-4-isopropylcyclohexanecarbonyl)-D-phenylalanine), a novel amino acid derivative with hypoglycemic activity, have been elucidated by mass spectrometry and nuclear magnetic resonance. Four of these (M1, M2, M3 and M8) were determined to be hydroxyl derivatives of AY4166, two (M9 and M10) were carboxylate derivatives via oxidization of M2 and M3, three (M4, M5 and M6) were glucronic acid conjugates and the other (M7) was a dehydro derivative. The estimated structures for M1, M2, M3, M7, Ms, M9 and MIO were confirmed by the coincidence of the retention time of HPLC, MS and H-1 NMR spectra between the isolated metabolites and authentic synthesized substances. For three glucronic acid conjugates, M4, M5 and M6, structural confirmation was performed by a selective enzymatic digestion with beta-glucronidase. M1 and M2/3 were about 5-6 and 3 times less potent than AY4166, respectively, and M7 was almost as potent as AY4166. Copyright (C) 1996 Elsevier Science Ltd