Methyl epijasmonate | 39924-52-2

• 物质功能分类: 香精与香料 - 合成香料 - 羧酸及酯类香料
• 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 epijasmonate
• 英文别名: methyl 2-[(1S,2R)-3-oxo-2-[(E)-pent-2-enyl]cyclopentyl]acetate
• CAS: 39924-52-2；1211-29-6
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: GEWDNTWNSAZUDX-BXXZLRJFSA-N

物化性质

• 比旋光度：
  D -76.5° (c = 3.4 in CH3OH)
• 沸点：
  110 °C0.2 mm Hg(lit.)
• 密度：
  1.03 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 溶解度：
  Almost insoluble in water, soluble in alcohol and oils.
• LogP：
  2.12
• 物理描述：
  Colourless oily liquid; Powerful floral-herbaceous, sweet aroma
• 颜色/状态：
  Colorless liquid
• 气味：
  Sharp persistent odor
• 蒸汽压力：
  3.37X10-4 mm Hg at 25 °C (est)
• 旋光度：
  Specific optical rotation: -76.5 deg at 25 °C/D (concn = 3.4 in CH3OH)
• 分解：
  Hazardous decomposition products formed under fire conditions. - Carbon oxides
• 气味阈值：
  Aroma threshold values: Detection: 5.7 ppm
• 折光率：
  Index of refraction: 1.4730 at 21.8 °C/D
• 保留指数：
  1614

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

ADMET

毒理性

• 相互作用

调查人员研究了甲基茉莉酸与蔗糖结合对葡萄细胞悬浮液中防御相关基因表达、芪类化合物和花青素产生的影响。甲基茉莉酸/蔗糖处理有效地刺激了苯丙氨酸氨裂合酶、查耳酮合酶、芪类化合物合酶、UDP-葡萄糖：类黄酮-O-葡萄糖基转移酶、蛋白水解酶抑制剂和几丁质酶基因的表达，并触发了细胞中piceids（芪苷）和花青素的积累，以及胞外介质中反式白藜芦醇和piceids（芪苷）的积累...

/Investigators/ studied the effects of methyl jasmonate in combination with sucrose on defense-related gene expression, stilbene and anthocyanin production in grapevine cell suspensions. The methyl jasmonate/sucrose treatment was effective in stimulating phenylalanine ammonia lyase, chalcone synthase, stilbene synthase, UDP-glucose: flavonoid-O-glucosyltransferase, proteinase inhibitor and chitinase gene expression, and triggered accumulation of both piceids and anthocyanins in cells, and trans-resveratrol and piceids in the extracellular medium...

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

辣椒（Capsicum annuum）悬浮细胞培养物被用来评估环糊精和茉莉酸甲酯作为防御反应诱导剂的效果。诱导的防御反应包括倍半萜和植物甾醇的积累以及相关致病蛋白的激活，这些反应在诱导过程中加强了细胞壁结构并保护细胞免受生物胁迫。结果显示，添加环糊精和茉莉酸甲酯都能诱导两种倍半萜，香树烯和索拉韦通酮的生物合成。这种反应显然是协同的，因为这两种化合物水平的提高在有这两种诱导剂共同存在时比它们单独使用时要高得多。在联合处理中，植物甾醇的生物合成也被诱导，这是由于加性效应的结果。同样，茉莉酸甲酯的外部应用诱导了相关致病蛋白的积累。细胞外蛋白质组分析显示存在与PR1和4、NtPRp27样蛋白和I类几丁质酶、过氧化物酶以及水解酶LEXYL1和2、阿拉伯糖苷酶、果胶酶、花蜜蛋白IV和富含亮氨酸重复蛋白同源的氨基酸序列，这表明茉莉酸甲酯在介导辣椒中防御相关基因产物表达方面发挥作用。除了这些由茉莉酸甲酯诱导的蛋白外，其他PR蛋白在辣椒的对照和诱导细胞培养中都被发现。这些包括IV类几丁质酶、β-1,3-葡萄糖苷酶、thaumatin样蛋白和过氧化物酶，这表明它们的表达主要是组成型的，因为它们参与生长、发育和防御过程。

Capsicum annuum /(C. annuum)/ suspension cell cultures were used to evaluate the effect of cyclodextrins and methyl jasmonate as elicitors of defense responses. The induced defense responses included the accumulation of sesquiterpenes and phytosterols and the activation of pathogenesis-related proteins, leading to reinforcement and modification of the cell wall architecture during elicitation and protection cells against biotic stress. The results showed that the addition of both cyclodextrins and methyl jasmonate induced the biosynthesis of two sesquiterpenes, aromadendrene and solavetivone. This response was clearly synergistic since the increase in the levels of these compounds was much greater in the presence of both elicitors than when they were used separately. The biosynthesis of phytosterols was also induced in the combined treatment, as the result of an additive effect. Likewise, the exogenous application of methyl jasmonate induced the accumulation of pathogenesis-related proteins. The analysis of the extracellular proteome showed the presence of amino acid sequences homologous to PR1 and 4, NtPRp27-like proteins and class I chitinases, peroxidases and the hydrolytic enzymes LEXYL1 and 2, arabinosidases, pectinases, nectarin IV and leucin-rich repeat protein, which suggests that methyl jasmonate plays a role in mediating defense-related gene product expression in C. annuum. Apart from these methyl jamonate-induced proteins, other PR proteins were found in both the control and elicited cell cultures of C. annuum. These included class IV chitinases, beta-1,3-glucanases, thaumatin-like proteins and peroxidases, suggesting that their expression is mainly constitutive since they are involved in growth, development and defense processes.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

硼是植物所需的一种微量元素，但如果在土壤中过量存在，对某些植物如含有青蒿素（一种重要的抗疟疾药物）的青蒿（Artemisia annua L.，又称A. annua）来说，它会对植物产生毒性。青蒿素是一种带有内过氧桥的倍半萜内酯...当前的研究旨在确定外源施用茉莉酸甲酯（MeJA）是否能对抗土壤中过量硼（B）带来的不利影响。根据获得的结果，硼毒性引起的氧化应激显著降低了植物的株高以及鲜重和干重。土壤中过量的硼也降低了叶片的净光合速率、气孔导度、内部CO2浓度和总叶绿素含量。相比之下，叶面施用MeJA增强了受胁迫和未受胁迫植物的生长和光合效率。过量的硼水平也增加了抗氧化酶如过氧化氢酶、过氧化物酶和超氧化物歧化酶的活性...将MeJA应用于受胁迫的植物减少了脂质过氧化的量并刺激了抗氧化酶的合成，同时提高了青蒿素的含量和产量。因此，可以得出结论，MeJA可能用于缓解硼毒性，并提高青蒿植物中青蒿素含量和产量。

Boron is an essential plant micronutrient, but it is phytotoxic if present in excessive amounts in soil for certain plants such as Artemisia annua L. /(A. annua)/ that contains artemisinin (an important antimalarial drug) in its areal parts. Artemisinin is a sesquiterpene lactone with an endoperoxide bridge... the present research was conducted to determine whether the exogenous application of methyl jasmonate (MeJA) could combat the ill effects of excessive /Boron stress/ (B) present in the soil. According to the results obtained, the B toxicity induced oxidative stress and reduced the stem height as well as fresh and dry masses of the plant remarkably. The excessive amounts of soil B also lowered the net photosynthetic rate, stomatal conductance, internal CO2 concentration and total chlorophyll content in the leaves. In contrast, the foliar application of MeJA enhanced the growth and photosynthetic efficiency both in the stressed and non-stressed plants. The excessive B levels also increased the activities of antioxidant enzymes, such as catalase, peroxidase and superoxide dismutase... the MeJA application to the stressed plants reduced the amount of lipid peroxidation and stimulated the synthesis of antioxidant enzymes, enhancing the content and yield of artemisinin as well. Thus, it was concluded that MeJA might be utilized in mitigating the B toxicity and improving the content and yield of artemisinin in A. annua plant.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中和。如果患者停止呼吸，请开始人工呼吸，最好使用需求阀复苏器、球囊阀面罩设备或口袋面罩，按训练操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果患者呕吐，让患者向前倾或将其置于左侧（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗帮助。 /毒物A和B/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。预防癫痫发作，如有必要，进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）持续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能够吞咽，有强烈的干呕反射，并且不流口水，冲洗口腔并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S61
• 危险类别码：
  R22,R36,R52/53
• WGK Germany：
  2,3

制备方法与用途

简介

茉莉酸甲酯（缩写 MeJA）是一种挥发性有机物，用于植物防卫和许多不同的发育途径，如种子发芽、根的生长、开花、果实成熟与植物老化。它源自茉莉酸，由S-腺苷-L-甲硫氨酸:茉莉酸羧基甲基转移酶催化产生。

作用机制

当植物遭遇生物或非生物胁迫时（特别是食草生物或创伤），会生成茉莉酸和茉莉酸甲酯，并堆积在受损部位。茉莉酸甲酯会向植物的防御系统发出信号，也可以通过物理接触或空气传播，在未受损的植物中产生防御反应。未受损的植物可以通过气孔或叶细胞的细胞质扩散吸收空气中的茉莉酸甲酯，从而在遭受胁迫时产生茉莉酸甲酯，既用于内部防御又是向其他植物的信号传导化合物。

食品添加剂最大允许使用量及残留标准

添加剂中文名称	允许使用该种添加剂的食品中文名称	添加剂功能	最大允许使用量（g/kg）	最大允许残留量（g/kg）
茉莉酮酸甲酯	食品	食品用香料	用于配制香精的各香料成分不得超过在GB 2760中的最大允许使用量和最大允许残留量

化学性质：无色油状液体，沸点94℃/6.7 Pa，相对密度1.021，折射率1.4730，溶于乙醇与油类。具有强烈的花香、青滋香，带有甜而持久的大花茉莉净油样的花香。

用途：广泛用于人工配制茉莉净油中，也用于茉莉香基中，但因价格较高，实际应用尚未普及。

文献信息

• US7250160B2
  申请人：——

  公开号：US7250160B2

  公开（公告）日：2007-07-31