methyl (2Z,4E)-5-((1S,4S)-1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoic acid | 39701-87-6

• 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: methyl (2Z,4E)-5-((1S,4S)-1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoic acid
• 英文别名: (1'S,4'S)-methyl 1',4'-trans-dihydroxy-α-ionylideneacetate；methyl trans-1',4'-dihydroxy-α-ionylideneacetate；1',4'-trans-diol abscisic acid methyl ester；1',4'-trans-diol of ABA-Me；ω-<1'α.4'β-Dihydroxy-2'.6'.6'-trimethyl-cyclohexen-(2')-yl>-3-methyl-pentadien-(2.4)-saeuremethylester；ω-(1'α.4'β-Dihydroxy-2'.6'.6'-trimethyl-cyclohexen-(2')-yl)-3-methyl-pentadien-(2.4)-saeuremethylester；Methyl (2Z,4E)-5-[(1S,4S)-1,4-dihydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl]-3-methyl-2,4-pentadienoate；methyl (2Z,4E)-5-[(1S,4S)-1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate
• CAS: 39701-87-6
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: XOIABPLHYNPUNG-UPMDNICRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2Z,4E)-5-((1S,4S)-1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoic acid 在 氢氧化钾 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2Z,4E)-5-[(1S,4S)-1-hydroxy-4-methoxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid
  参考文献：
  名称：

  Synthesis and biological activity of 4′-methoxy derivatives of abscisic acid

  摘要：

  Replacing the 4'-carbonyl group of abscisic acid with a methoxy group does not affect the abscisic acid (ABA)-like activities of the product in barley aleurone protoplasts, although the reduction of ABA to 4'-hydroxyl derivatives significantly reduces the ABA-like activity of the products. This suggests that methoxy derivatives of abscisic acid might be used to produce probes for ABA binding proteins. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00302-4
• 作为产物：
  描述：

  (+)-脱落酸 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 2.0h， 生成 methyl (2Z,4E)-5-((1S,4S)-1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoic acid
  参考文献：
  名称：

  Isolation of 4′-dihydroabscisic acid from immature seeds of Vicia faba

  摘要：

  DOI：

  10.1016/s0031-9422(82)85068-1

文献信息

• ABSCISIC ACID DERIVATIVE
  申请人：NATIONAL UNIVERSITY CORPORATION SHIZUOKA UNIVERSITY

  公开号：US20170283375A1

  公开（公告）日：2017-10-05

  The compound represented by formula (IV) or a salt thereof has an inhibitory action on an abscisic acid receptor. The compound or the salt thereof can be used as a plant growth regulator. wherein X is an ethylene group, an ethenylene group or an ethynylene group, R 1 is a hydrogen atom, a phenyl group or a naphthyl group, and the phenyl group and naphthyl group each optionally have a substituent selected from the group consisting of a halogen atom, a hydroxyl group, a C1-6 alkyl group, a C1-6 alkyl group substituted with a halogen atom, a C1-6 alkoxy group, an acetyl group, an amino group, an acetylamino group, a phenyl group and a pentafluorosulfanyl group.

  公式（IV）所代表的化合物或其盐具有对脱落酸受体的抑制作用。该化合物或其盐可用作植物生长调节剂。其中X是乙烯基，乙烯基或乙炔基，R1是氢原子，苯基或萘基，苯基和萘基各自可选地具有从卤素原子，羟基，C1-6烷基，C1-6烷基取代的卤素原子，C1-6烷氧基，乙酰基，氨基，乙酰氨基，苯基和五氟硫基中选择的取代基。
• The stability of the 1′,4′-diols of abscisic acid
  作者：G.T. Vaughan、B.V. Milborrow

  DOI：10.1016/0031-9422(88)83093-0

  日期：1988.1

  Abstract The 1′,4′- cis and 1′,4′- trans -diols of abscisic acid (ABA) are unstable in acidic conditions: they interconvert and oxidize to ABA. When the diols were held in acidic (pH 4) [ 18 O]H 2 O the oxygen atoms of both the 1′- and 4′-hydroxyl groups exchanged with the medium with retention and inversion of configuration. Thus the (+)-[2- 14 C]- trans -diol was epimerized to the (+)-[2- 14 C]- cis -diol

  摘要 脱落酸 (ABA) 的 1',4'- 顺式和 1',4'- 反式二醇在酸性条件下不稳定：它们相互转化并氧化为 ABA。当二醇保持在酸性 (pH 4) [ 18 O]H 2 O 中时，1'- 和 4'- 羟基的氧原子与介质交换，同时保留和反转构型。因此，(+)-[2- 14 C]-反式-二醇差向异构化为(+)-[2- 14 C]-顺式-二醇和(-)-[2- 14 C]-顺式-二醇。类似地，[1'- 18 O ] 顺式和 [1'- 18 O] 反式二醇在差向异构化过程中损失了 18 O。反式二醇更稳定约 30%，也更不容易氧化成 ABA。顺式二醇的显着差向异构发生在 pH 6 以下，而反式二醇的等效反应发生在 pH 5 以下。
• Oritani, Takayuki; Yamashita, Kyohei, Agricultural and Biological Chemistry, 1987, vol. 51, # 1, p. 275 - 278
  作者：Oritani, Takayuki、Yamashita, Kyohei

  DOI：——

  日期：——
• Yamamoto, Hiroshi; Oritani, Takayuki, Bioscience, Biotechnology and Biochemistry, 1994, vol. 58, # 5, p. 992 - 994
  作者：Yamamoto, Hiroshi、Oritani, Takayuki

  DOI：——

  日期：——
• Oritani, Takayuki; Ichimura, Michio; Yamashita, Kyohei, Agricultural and Biological Chemistry, 1984, vol. 48, # 6, p. 1677 - 1678
  作者：Oritani, Takayuki、Ichimura, Michio、Yamashita, Kyohei

  DOI：——

  日期：——