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Methyl jasmonate | 193333-55-0

中文名称
——
中文别名
——
英文名称
Methyl jasmonate
英文别名
methyl 2-[(1R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetate
Methyl jasmonate化学式
CAS
193333-55-0
化学式
C13H20O3
mdl
——
分子量
224.3
InChiKey
GEWDNTWNSAZUDX-JXWYNLIVSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

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甲基茉莉酸作为诱导防御反应的激发剂的效果。诱导的防御反应包括倍半萜和植物甾醇的积累以及与病原相关的蛋白的激活,这些反应在激发和保护细胞对抗生物胁迫期间加强了细胞壁结构的加固和修饰。结果表明,添加环糊精和甲基茉莉酸都能诱导两种倍半萜,即香树烯和索拉维通酮的生物合成。这种反应是明显的协同作用,因为当两种激发剂同时使用时,这些化合物的水平增加远大于它们单独使用时的水平。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,外源应用甲基茉莉酸诱导了与病原相关的蛋白的积累。对外泌蛋白质组进行分析显示,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和富含亮氨酸的重复蛋白同源的氨基酸序列,这表明甲基茉莉酸在介导辣椒中防御相关基因产物的表达中发挥作用。除了这些由甲基茉莉酸诱导的蛋白外,其他PR蛋白在辣椒的控制组和诱导组细胞培养中都有发现。这些包括IV类几丁质酶、beta-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,让患者身体前倾或将其置于左侧(如果可能,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。寻求医疗救助。 /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,协助通气。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……。预期癫痫发作,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、有强烈的干呕反射且不流口水,则用温水冲洗口腔,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)

上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    Methyl jasmonate1,2-乙二硫醇三氟化硼乙醚 作用下, 以 二氯甲烷 为溶剂, 以63%的产率得到1,3-Dithiolane methyl jasmonate
    参考文献:
    名称:
    Structural Requirements of Jasmonates and Mimics for Nicotine Induction inNicotiana sylvestris
    摘要:
    DOI:
    10.1023/a:1022515127437
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文献信息

  • 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,
  • Structural Requirements of Jasmonates and Mimics for Nicotine Induction inNicotiana sylvestris
    作者:Zong-Ping Zhang、Thomas Krumm、Ian T. Baldwin
    DOI:10.1023/a:1022515127437
    日期:1997.12
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