7-异-葫芦酸甲酯 | 146143-03-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 7-异-葫芦酸甲酯
• 英文名称: 7-iso-cucurbic acid methyl ester
• 英文别名: methyl 7-epi-cucurbate；methyl 2-[(1R,2R,3S)-3-hydroxy-2-[(Z)-pent-2-enyl]cyclopentyl]acetate
• CAS: 146143-03-5
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: OOYCGMQJIWHWHA-UMOJZNBSSA-N

物化性质

• 沸点：
  309.9±15.0 °C(Predicted)
• 密度：
  1.010±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-异-葫芦酸甲酯 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到茉莉酸甲酯
  参考文献：
  名称：

  脂肪酶催化的茉莉酸甲酯两种对映体的制备

  摘要：

  两种对映体茉莉酮酸甲酯1的制备都是通过脂肪酶催化的（±）-甲基7-表哌草酸酯3的拆分而实现的。脂肪酶P（Amano）对（±）-3（E = 370）的酰化和相应的乙酸酯（E = 41）的水解均具有良好的选择性。（±）-甲基6,7-二甲基吡啶甲酸2的拆分结果较差。发现（6 R，7 S）-构型适合于选择性酶促反应，并且底物的C-（3）立体化学不影响酶促反应。

  DOI：

  10.1016/s0957-4166(01)00169-0
• 作为产物：
  描述：

  茉莉酸 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 7-异-葫芦酸甲酯
  参考文献：
  名称：

  葫芦酸及其6,7-立体异构体

  摘要：

  摘要 以(-)-茉莉酸(JA)为原料制备了7-异葫芦酸(7-iso-CA)和6-epi-7-异葫芦酸(6-epi-7-iso-CA)衍生物。通过从 (+)-7-异-茉莉酸 (7-iso-JA) 还原和葫芦酸 (CA) 和 6-epi - 葫芦酸 (6-epi -CA)。描述了这些衍生物的色谱特性（TLC、HPLC、GC）并通过物理数据确定了结构。对不同植物材料的提取物进行了 JA 和 CA 及其 6,7-立体异构体的天然存在分析。JA, 6-epi -CA 和 6-epi -7-iso -CA 在胡桃的雌花中被鉴定出来，JA, CA, 6-epi -CA 和 6-epi -7-iso -CA 在胡桃的孢子中被鉴定. JA, CA, 6-epi-CA 和 9, 10-dihydro-JA 在 Secalemerice 的未成熟果核中检测到。在黑麦 JA 中占主导地位的幼果，而CA水平超过了早熟果实中JA的量。在每个组织中，发现

  DOI：

  10.1016/0031-9422(91)85038-2

文献信息

• Synthesis and Bioactivity of Potassium β-<scp>D</scp>-Glucopyranosyl 12-Hydroxy Jasmonate and Related Compounds
  作者：Yoko NAKAMURA、Ryoji MIYATAKE、Sho INOMATA、Minoru UEDA

  DOI：10.1271/bbb.80338

  日期：2008.11.23

  Albizzia saman, a leguminous plant, is known to open its leaves in the daytime and sleep at night with the leaves folded. β-d-Glucopyranosyl 12-hydroxyjasmonate (1) was isolated as an endogenous chemical factor controlling this leafmovement. We developed a concise synthesis of optically pure (−)-1 in 9 steps from (+)-2 with a total yield of 58%. Similarly, such analogs of 1 as epi-LCF (13), enantiomer (14), and galactoside (19) were synthesized for a structure activity relationship (SAR) study. The results of this SAR study strongly suggest that the mechanism for the leaf-closing activity of 1 would be different from that of methyl jasmonate, and also suggest the involvement of a different kind of target protein which recognizes the trans-isomer of a jasmonate derivative.

  Albizzia SAman是一种豆科植物，它在白天气息张开的叶子，夜间则将叶子折叠休息。β-d-葡萄糖吡喃苷12-羟基茉莉酸酯（1）被鉴定为控制这种叶子运动的内源性化学因子。我们开发了一种简洁的合成方法，通过9个步骤从（+）-2合成光学上纯净的（−）-1，总产率为58%。同样，作为结构-活性关系（SAR）研究的类物质1的类似物，如epi-LCF（13）、对映体（14）和半乳糖苷（19）也被合成。SAR研究的结果强烈表明，1的闭叶活性的机制与甲基茉莉酸酯的机制不同，并且还表明涉及了一种不同类型的靶蛋白，该蛋白识别茉莉酸衍生物的反式异构体。
• Easy Preparation of Methyl 7-<i>epi</i>-Jasmonate and Four Stereoisomers of Methyl Cucurbate, and Assessment of the Stereogenic Effect of Jasmonate on Phytohormonal Activities
  作者：Hideharu SETO、Emi NOMURA、Shozo FUJIOKA、Hiroyuki KOSHINO、Toshiro SUENAGA、Shigeo YOSHIDA

  DOI：10.1271/bbb.63.361

  日期：1999.1

  stereogenic effect of jasmonate on phytohormonal activities, methyl 7-epi-jasmonate (1b) and four stereoisomers of methyl cucurbate were easily prepared in racemic form: epimerization at the C-7 position of a commercially available methyl jasmonate (2b) with a base and subsequent fractional distillation gave a 46:54 mixture of 1b and 2b, whose reduction gave a mixture of methyl cucurbates (3-6). This

  为了测试茉莉酸甲酯对植物激素活性的立体效应，很容易以消旋形式制备7-表茉莉酮酸甲酯（1b）和四种葫芦酸甲酯的立体异构体：在市场上可买到的茉莉酸甲酯（2b）的C-7位差向异构体碱和随后的分馏得到1b和2b的46∶54混合物，其还原得到小葫芦酸甲酯（3-6）的混合物。通过分子建模和对1b和2b的NMR研究，对这种合成化学方法进行了补充。对制得的茉莉酸酯对水稻第二片叶鞘的生长和水芹种子发芽的抑制活性的评估表明，茉莉酸酯的C-3和C-7侧链的顺式构型是影响茉莉酸酯的重要因素。高活动。在抑制水芹种子发芽的过程中，
• Effects of natural and novel synthetic jasmonates in experimental metastatic melanoma
  作者：D Reischer、A Heyfets、S Shimony、J Nordenberg、Y Kashman、E Flescher

  DOI：10.1038/sj.bjp.0707146

  日期：2007.3

  Background and purpose:No current treatment reliably affects the course of metastatic melanoma. Consequently, novel approaches to the control of metastasis are actively sought. The overall goal of the present study was to identify new anti‐metastatic agents active against melanoma cells.Experimental approach:Two directions were taken: 1. To determine whether the natural plant hormone methyl jasmonate, which kills cancer cells selectively, can suppress the characteristic metastatic behavior of B16‐F10 melanoma cells; 2. To synthesize and identify novel jasmonate derivatives with better cytotoxic and anti‐metastatic activities than methyl jasmonate.Key results:We found that methyl jasmonate suppressed B16‐F10 cell motility and inhibited the development of experimental lung metastases of these cells. Furthermore, methyl jasmonate suppressed the motility of a sub‐clone of these cells over‐expressing P‐glycoprotein and exhibiting multidrug resistance. The synthetic derivative Compound I (5,7,9,10‐tetrabromo derivative of methyl jasmonate, the most active derivative) had greater cytotoxic potency (IC50, 0.04mM) than methyl jasmonate (IC50, 2.6mM). Compound I prevented B16‐F10 cell adhesion efficiently and inhibited the development of lung metastases at a much lower dose than methyl jasmonate.Conclusions and Implications:Natural and synthetic jasmonates have anti‐metastatic actions. Further development of these agents for the suppression of metastasis in melanoma and other types of cancer is warranted.British Journal of Pharmacology (2007) 150, 738–749. doi:10.1038/sj.bjp.0707146