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methyl jasmonate | 755005-33-5

中文名称
——
中文别名
——
英文名称
methyl jasmonate
英文别名
Jasmonic acid methyl ester;methyl 2-[(1R,2R)-3-oxo-2-pent-2-enylcyclopentyl]acetate
methyl jasmonate化学式
CAS
755005-33-5
化学式
C13H20O3
mdl
——
分子量
224.3
InChiKey
GEWDNTWNSAZUDX-GHMZBOCLSA-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蔗糖结合对葡萄细胞悬浮液中防御相关基因表达、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裂合酶、查耳酮合酶、合成酶、UDP-葡萄糖花青素-O-葡萄糖基转移酶、蛋白解酶抑制剂几丁质酶基因的表达,并触发了细胞中piceids(苷)和花青素的积累,以及胞外介质中反式白藜芦醇和piceids(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相关蛋白的激活,这些蛋白在激发和保护细胞对抗生物胁迫期间强化和修改细胞壁结构。结果表明,添加环糊精和甲基茉莉酸都能诱导两种倍半萜香树烯和索拉维通酮的生物合成。这种反应显然是协同的,因为这两种化合物平的增加在有这两种激发剂存在时比它们单独使用时要大得多。在联合处理中也诱导了植物甾醇的生物合成,这是由于加性效应。同样,外源应用甲基茉莉酸诱导了相关蛋白的积累。对细胞外蛋白质组进行分析,发现存在与PR1和4、NtPRp27样蛋白和I类几丁质酶过氧化物酶以及解酶LEXYL1和2、阿拉伯糖苷酶、果胶酶、花蜜蛋白IV和富含亮酸重复蛋白同源的氨基酸序列,这表明甲基茉莉酸在调节C. annuum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,还在C. annuum的对照和激发细胞培养中发现了其他PR蛋白。这些包括IV类几丁质酶、beta-1,3-葡聚糖酶、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
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(B)带来的不利影响。根据获得的结果,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毒物清除。如果患者停止呼吸,开始人工呼吸,最好使用需求阀复苏器、袋阀面罩装置或口袋面罩,按训练操作。如有必要,执行心肺复苏。立即用缓慢流动的冲洗受污染的眼睛。不要催吐。如果发生呕吐,让患者前倾或置于左侧(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,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,立即用冲洗眼睛。在运输过程中,用0.9%的生理盐(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,则用温冲洗口腔,并给予5毫升/千克,最多200毫升的进行稀释……。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)

反应信息

  • 作为反应物:
    描述:
    methyl jasmonate 在 sodium tetrahydroborate 作用下, 以 甲醇 为溶剂, 反应 1.0h, 以28 mg的产率得到methyl 2-((1R,2R,3R)-3-hydroxy-2-(pent-2-en-1-yl)cyclopentyl)acetate
    参考文献:
    名称:
    Antimalarial Evaluation of the Chemical Constituents of Hairy Root Culture of Bixa orellana L.
    摘要:
    全世界每年报告的疟疾病例超过 2.16 亿例,其中约三分之一的病例(主要是五岁以下儿童)在感染后无法存活。尽管疟疾对世界健康产生了重大影响,但目前可用的治疗药物数量有限。如果出现多重耐药菌株,缺乏支架多样性就会构成威胁。在过去的一个世纪中,陆地天然产品为许多获得美国食品及药物管理局批准的药物提供了化学多样性的主要起始原料来源。Bixa orellana L. 是南美洲一种常用于治疗疟疾的植物。为了寻找新的潜在治疗药物,研究人员利用核磁共振和质谱分析方法对 Bixa orellana L. 毛根培养品系的化学成分进行了表征,然后对其进行了抗疟疾菌株 3D7 和 K1 的生物评估。粗提取物及其分离化合物的 EC50 值在微摩尔范围内。在此,我们报告了从毛根中提取的 Bixa orellana L. 的化学成分对所观察到的抗疟活性的影响。
    DOI:
    10.3390/molecules19010756
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文献信息

  • ANTIPERSPIRANT AND DEODORANT COMPOSITIONS COMPRISING MALODOR REDUCTION COMPOSITIONS
    申请人:The Procter & Gamble Company
    公开号:US20160089317A1
    公开(公告)日:2016-03-31
    The present invention relates to antiperspirant and deodorant compositions comprising malodor reduction compositions and methods of making and using such antiperspirant and deodorant compositions. Such antiperspirant and deodorant compositions comprising the malodor control technologies disclosed herein provide malodor control without leaving an undesirable scent and when perfume is used to scent such compositions, such scent is not unduely altered by the malodor control technology.
  • CLEANING AND/OR TREATMENT COMPOSITIONS COMPRISING MALODOR REDUCTION COMPOSITIONS
    申请人:The Procter & Gamble Company
    公开号:US20160090555A1
    公开(公告)日:2016-03-31
    The present invention relates to cleaning and/or treatment compositions comprising malodor reduction compositions and methods of making and using such cleaning and/or treatment compositions and malodor reduction compositions. As a result, such malodor reduction compositions do not unduely interfere with the scent of the perfumed or unperfumed cleaning and/or treatment compositions that comprise such compositions and the perfumed or unperfumed situs that is treated with such cleaning and/or treatment compositions.
  • PERSONAL CARE COMPOSITIONS COMPRISING MALODOR REDUCTION COMPOSITIONS
    申请人:The Procter & Gamble Company
    公开号:US20160089318A1
    公开(公告)日:2016-03-31
    The present invention relates to personal care compositions comprising malodor reduction compositions and methods of making and using such personal care compositions. Such personal care compositions comprising the malodor control technologies disclosed herein provide malodor control without leaving an undesirable scent and when perfume is used to scent such compositions, such scent is not unduly altered by the malodor control technology.
  • FRESHENING COMPOSITIONS AND DEVICES COMPRISING SAME
    申请人:The Procter & Gamble Company
    公开号:US20160089462A1
    公开(公告)日:2016-03-31
    The present invention relates to freshening compositions and devices comprising same that comprise a composition having a viscosity of from about 1 mPa·s to about 50,000 mPa·s comprising malodor reduction compositions and methods of making and using such compositions. The disclosed malodor reduction compositions do not unduely interfere with the scent of the freshening compositions and devices that comprise such technologies and the perfumed or unperfumed situs that is treated with such freshening compositions and devices.
  • DELIVERY SYSTEMS COMPRISING MALODOR REDUCTION COMPOSITIONS
    申请人:The Procter & Gamble Company
    公开号:US20160090558A1
    公开(公告)日:2016-03-31
    The present invention relates to delivery systems comprising malodor reduction compositions, methods of making such delivery systems and consumer products made with such delivery systems. Such delivery systems do not unduely interfere with the scent of the perfumed or unperfumed delivery system, perfumed or unperfumed products comprising such delivery systems and any perfumed or unperfumed situs that is treated with such products.
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