(+/-)-methyl 12-hydroxyjasmonate | 81761-06-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+/-)-methyl 12-hydroxyjasmonate
• 英文别名: methyl 2-[(1S,2S)-2-[(Z)-5-hydroxypent-2-enyl]-3-oxocyclopentyl]acetate
• CAS: 81761-06-0；92934-65-1
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: XCZTYYQNVNLGKI-NPRAVPSUSA-N

物化性质

• 沸点：
  363.8±17.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  (+/-)-methyl 12-hydroxyjasmonate 在 氢氧化钾 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 8.5h， 生成 {(1S,2S)-2-[(Z)-5-((2R,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-pent-2-enyl]-3-oxo-cyclopentyl}-acetic acid
  参考文献：
  名称：

  Enantio-differential approach to identify the target cell for glucosyl jasmonate-type leaf-closing factor, by using fluorescence-labeled probe compounds

  摘要：

  Potassium beta-D-glucopyranosyl 12-hydroxyjasmonate (1) is a leaf-closing factor of Albizzia plants that induces nyctinastic leaf closure. In this paper, we synthesized probe 3 and its congener 4 by using a pair of enantiomerically pure methyljasmonate that was prepared by using optical resolution, and carried out fluorescence studies using 3 and 4 to identify the target cell of 1. The probe 3 bound to the motor cells of two Albizzia plants, whereas it could not bind to the motor cells of plants belonging to other genus. On the other hand, probe 4 did not bind to the motor cell at all. These results suggested that a specific receptor for I is involved in the motor cell of Albizzia plants. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.092
• 作为产物：
  描述：

  methyl (1R,2S,2'Z)-3-oxo-2-[5'-(tetrahydropyran-2''-yl)oxy-2'-pentenyl]-cyclopentaneacetate 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以87%的产率得到(+/-)-methyl 12-hydroxyjasmonate
  参考文献：
  名称：

  Synthesis and Bioactivity of Potassium β-D-Glucopyranosyl 12-Hydroxy Jasmonate and Related Compounds

  摘要：

  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。

  DOI：

  10.1271/bbb.80338

文献信息

• <i>Michael</i>-Addition von Thiocarbonsäureestern Anwendung bei der Synthese von (±)-Jasminketolacton
  作者：Hans Gerlach、Peter Künzler

  DOI：10.1002/hlca.19780610721

  日期：1978.11.1

  Michael addition of carbothioates. Application to the synthesis of (±)-jasmine ketolactone

  迈克尔加硫代碳酸盐。在合成（±）-茉莉酮内酯中的应用
• Functional importance of the sugar moiety of jasmonic acid glucoside for bioactivity and target affinity
  作者：Minoru Ueda、Gangqiang Yang、Yuuki Nukadzuka、Yasuhiro Ishimaru、Satoru Tamura、Yoshiyuki Manabe

  DOI：10.1039/c4ob02106a

  日期：——

  Importance of the d-glycopyranoside structure for the bioactivity and target affinity of jasmonic acid glucoside.

  "

  d-葡萄糖苷结构对茉莉酸葡萄糖苷的生物活性和靶标亲和力的重要性。

  "
• Cardioactive steroid saponins and other constituents from the aerial parts of tribulus cistoides☆
  作者：Hans Achenbach、Harald Hübner、Wolfgang Brandt、Melchior Reiter

  DOI：10.1016/s0031-9422(00)86890-9

  日期：1994.4.19

  From the petrol extract of the aerial parts of Tribulus cistoides three steroid sapogenins and two N-acyltyramines were isolated, whereas the methanolic extract gave nine steroid saponins, among them the cardioactive cistocardin, saponin-3, saponin-4 and saponin-7. Furthermore, a furostanol diglycoside was isolated besides 5'-(hydroxysulphonyloxy) jasmonic acid, D-(+)-pinitol and sucrose. The structures

  从刺蒺藜地上部分的汽油提取物中分离出三种甾体皂苷元和两种 N-酰基酪胺，而甲醇提取物得到九种甾体皂苷，其中有心脏活性的cistocardin、saponin-3、saponin-4和saponin-7。此外，除5'-(羟基磺酰氧基)茉莉酸、D-(+)-松醇和蔗糖外，还分离了呋甾醇二糖苷。这些结构是通过对分离的化合物及其水解产物的光谱研究确定的。5'-(Hydroxysulphonyloxy)茉莉酸已通过部分合成制备。
• Synthesis of (±)-Methyl Tuberonate, a Potato Tuber-forming Substance, and Its Epimer
  作者：Hiromasa KIYOTA、Daisuke NAKASHIMA、Takayuki ORITANI

  DOI：10.1271/bbb.63.2110

  日期：1999.1

  Methyl esters of (±)-tuberonic acid and (±)-12-hydroxyjasmonic acid (trans-tuberonic acid), the aglycons of strong potato tuber-forming substances, were synthesized from norbornene via side-chain elongation and Baeyer-Villiger oxidation as key steps.

  以降冰片烯为原料，通过侧链伸长和贝耶-维利格氧化等关键步骤合成了(±)-琥珀酸和(±)-12-羟基茉莉酸（反式-琥珀酸）的甲酯，它们是马铃薯块茎形成物质的重要缩合物。
• Direct observation of the target cell for jasmonate-type leaf-closing factor: genus-specific binding of leaf-movement factors to the plant motor cell
  作者：Yoko Nakamura、Hiromasa Kiyota、Tsutomu Kumagai、Minoru Ueda

  DOI：10.1016/j.tetlet.2006.02.123

  日期：2006.4

  We report the synthesis of the novel fluorescence-labeled jasmonate glycoside 2 based on beta-D-glucopyranosyl 12-hydroxy-jasmonate 1, which is a leaf-closing substance of Albizzia Durazz. The fluorescence study using 2 revealed that the target cell for 1 is a motor cell. Probe 2 bound to the motor cells of two plants belonging to genus Albizzia. This result suggested that a receptor for 2, which is common among genus Albizzia would be involved in the nyctinastic leaf movement. (c) 2006 Elsevier Ltd. All rights reserved.