ethyl 14-carboxyretinoate | 113089-08-0

• 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: ethyl 14-carboxyretinoate
• 英文别名: (2E,4E,6E,8E)-2-ethoxycarbonyl-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
• CAS: 113089-08-0
• 化学式: C₂₃H₃₂O₄
• 分子量: 372.505
• InChiKey: RYTNEPWDZCZOFE-PPNLBOGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 14-carboxyretinoate 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以69%的产率得到14-carboxyretinoic acid
  参考文献：
  名称：

  Terminal bifunctional retinoids. Synthesis and evaluations related to cancer chemopreventive activity

  摘要：

  Retinoids that have two functional groups at the side-chain terminus have been synthesized. The two terminal functional groups are combinations of the carboxyl, carbethoxy, and N-(ethylamino)carbonyl groups. The synthesis route is based on the sodium amide catalyzed condensation of (E,E)-beta-ionylideneacetaldehyde with diethyl isopropylidenemalonate. Ethyl 14-carboxyretinoate (6), the initial bifunctional analogue, undergoes isomerization in unbuffered aqueous ethanol and reaches a state of equilibrium with ethyl 14-carboxy-13-cis-retinoate. Both of the possible amide-esters and amide-acids were obtained. The structures of the isomeric bifunctional analogues were established by studies of nuclear Overhauser effects. The bifunctional analogues induce differentiation of mouse embryonal carcinoma cells, and those analogues that have a free carboxyl group bind to cellular retinoic acid binding protein.

  DOI：

  10.1021/jm00401a011
• 作为产物：
  描述：

  亚异丙基丙二酸二乙酯 、 (7E,9E)-beta-离子亚基乙醛 在 sodium amide 作用下， 以 氨 为溶剂， 生成 ethyl 14-carboxyretinoate
  参考文献：
  名称：

  Terminal bifunctional retinoids. Synthesis and evaluations related to cancer chemopreventive activity

  摘要：

  Retinoids that have two functional groups at the side-chain terminus have been synthesized. The two terminal functional groups are combinations of the carboxyl, carbethoxy, and N-(ethylamino)carbonyl groups. The synthesis route is based on the sodium amide catalyzed condensation of (E,E)-beta-ionylideneacetaldehyde with diethyl isopropylidenemalonate. Ethyl 14-carboxyretinoate (6), the initial bifunctional analogue, undergoes isomerization in unbuffered aqueous ethanol and reaches a state of equilibrium with ethyl 14-carboxy-13-cis-retinoate. Both of the possible amide-esters and amide-acids were obtained. The structures of the isomeric bifunctional analogues were established by studies of nuclear Overhauser effects. The bifunctional analogues induce differentiation of mouse embryonal carcinoma cells, and those analogues that have a free carboxyl group bind to cellular retinoic acid binding protein.

  DOI：

  10.1021/jm00401a011

文献信息

• SHEALY, Y. FULMER;KRAUTH, CHARLES A.;RIORDAN, JAMES M.;SANI, BRAHMA P., J. MED. CHEM., 31,(1988) N 6, 1124-1130
  作者：SHEALY, Y. FULMER、KRAUTH, CHARLES A.、RIORDAN, JAMES M.、SANI, BRAHMA P.

  DOI：——

  日期：——
• Terminal bifunctional retinoids. Synthesis and evaluations related to cancer chemopreventive activity
  作者：Y. Fulmer Shealy、Charles A. Krauth、James M. Riordan、Brahma P. Sani

  DOI：10.1021/jm00401a011

  日期：1988.6

  Retinoids that have two functional groups at the side-chain terminus have been synthesized. The two terminal functional groups are combinations of the carboxyl, carbethoxy, and N-(ethylamino)carbonyl groups. The synthesis route is based on the sodium amide catalyzed condensation of (E,E)-beta-ionylideneacetaldehyde with diethyl isopropylidenemalonate. Ethyl 14-carboxyretinoate (6), the initial bifunctional analogue, undergoes isomerization in unbuffered aqueous ethanol and reaches a state of equilibrium with ethyl 14-carboxy-13-cis-retinoate. Both of the possible amide-esters and amide-acids were obtained. The structures of the isomeric bifunctional analogues were established by studies of nuclear Overhauser effects. The bifunctional analogues induce differentiation of mouse embryonal carcinoma cells, and those analogues that have a free carboxyl group bind to cellular retinoic acid binding protein.