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methyl jasmonate | 1089329-22-5

中文名称
——
中文别名
——
英文名称
methyl jasmonate
英文别名
trans-Methyljasmonat;3-methoxycarbonylmethyl-2-(cis-2'-pentenyl)-cyclopentanone;(Z)-methyl 2-(3-oxo-2-(pent-2-enyl)cyclopentyl)acetate;Methyl 2-(3-oxo-2-(pent-2-en-1-yl)cyclopentyl)acetate;methyl 2-[3-oxo-2-[(E)-pent-2-enyl]cyclopentyl]acetate
methyl jasmonate化学式
CAS
1089329-22-5
化学式
C13H20O3
mdl
MFCD00036656
分子量
224.3
InChiKey
GEWDNTWNSAZUDX-SNAWJCMRSA-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:
    0.692
  • 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、芪合成酶、UDP-葡萄糖:花青素-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,因为当两种激发剂同时使用时,这些化合物的水平增加远大于单独使用时的水平。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。同样,外源应用甲基茉莉酸诱导了相关蛋白的积累。对外泌体蛋白质组进行分析,发现了与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,这表明甲基茉莉酸在介导辣椒防御相关基因产物表达中发挥作用。除了这些由甲基茉莉酸诱导的蛋白外,还在辣椒悬浮细胞培养的控制组和激发组中发现了其他相关蛋白。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构成性的,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
硼是植物生长所需的一种微量元素,但对于含有青蒿素(一种重要的抗疟疾药物)的植物如黄花蒿(Artemisia annua L.,又称A. annua)来说,如果土壤中的硼含量过高,则会对植物产生毒性。青蒿素是一种带有过氧化物桥的倍半萜内酯...目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的硼(B)带来的不良影响。根据获得的结果,硼毒害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,叶面喷施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可能用于缓解硼毒害,并提高黄花蒿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,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)

反应信息

  • 作为反应物:
    描述:
    methyl jasmonate频那醇硼烷 在 Moris520 (Tapas) 作用下, 以 氘代苯 为溶剂, 反应 0.25h, 以99%的产率得到methyl (E)-2-(2-(pent-2-en-1-yl)-3-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)cyclopentyl)acetate
    参考文献:
    名称:
    通过温和的和化学选择性的羰基硼氢化反应,由Th-O键催化再生Th-H键†
    摘要:
    在这里,我们介绍了对act系元素催化的醛和酮进行空前的化学选择性氢硼化。在室温下,该反应具有极低的催化剂负载量(0.1–0.004 mol%),并且在不到15分钟的时间内形成了定量的产物。热力学和动力学研究,包括使用氘代频哪醇硼烷的化学计量和标记研究,使我们能够为通过羰基硼氢化的Th–H键的显着催化再生提出合理的机理。
    DOI:
    10.1039/c8cc05030a
  • 作为产物:
    描述:
    3-cyanomethyl-2-(cis-2'-pentenyl)-cyclopentanone 在 盐酸 、 sodium chloride 作用下, 以 甲醇 为溶剂, 以84%的产率得到methyl jasmonate
    参考文献:
    名称:
    Process for producing 3-cyanomethyl cyclopentanone derivatives
    摘要:
    揭示了一种生产3-氰甲基环戊酮衍生物的方法,这些衍生物是茉莉花和类似物中香味成分的有用前体,如甲基茉莉酸酯、甲基二氢茉莉酸酯等。在这个过程中,茉莉酸酯是从β-二酮化合物和叠氮化合物经过多步反应制备的。
    公开号:
    US04100184A1
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文献信息

  • Organic Compounds
    申请人:Schilling Boris
    公开号:US20100113460A1
    公开(公告)日:2010-05-06
    Disclosed are compounds having the ability to inhibit cytochrome P450 2A6, 2A13, and/or 2B6 and tobacco products comprising them. Also disclosed are pharmaceutical compositions comprising them.
    揭示了一种具有抑制细胞色素P450 2A6、2A13和/或2B6能力的化合物,以及包含它们的烟草产品。还披露了包含这些化合物的药物组合物。
  • [EN] METHODS FOR PREPARATION OF JASMONATE COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS DE JASMONATE
    申请人:VIDAC PHARMA LTD
    公开号:WO2019135243A1
    公开(公告)日:2019-07-11
    This invention relates to methods for preparation of jasmonate compounds via a salt of jasmonic acid.
    这项发明涉及通过茉莉酸盐制备茉莉酸酯化合物的方法。
  • Process for the preparation of alkylidenecyclopentanone derivatives
    申请人:Chapuis Christian
    公开号:US20050187299A1
    公开(公告)日:2005-08-25
    The present invention relates to the field of organic synthesis and more particularly to a new process for the preparation of a compound of formula (I), in the form of any one of its isomers or a mixture thereof, wherein, more preferably, G represents a C═O group, R 1 represents a butyl group and R 2 represents a methyl group. The process of the invention involves an 2-(1-hydroxyalkyl)-cyclopent-2-en-1-one derivative, as starting material, which can be then converted into a compound of formula (I) by a process comprising a thermal rearrangement. The 2-alkylidene-3-oxo-cyclopentylacetate derivative and the 2-(1-hydroxyalkyl)-cyclopent-2-en-1-one derivative are also an object of the invention.
    本发明涉及有机合成领域,更特别地涉及一种制备式(I)化合物的新工艺,其形式为其任何一个异构体或其混合物,其中,更优选地,G代表C═O基团,R1代表丁基基团,R2代表甲基基团。本发明的工艺涉及以2-(1-羟基烷基)-环戊-2-烯-1-酮衍生物为起始材料,该起始材料可以通过包括热重排的过程转化为式(I)化合物。2-烷基亚甲基-3-氧代环戊基乙酸酯衍生物和2-(1-羟基烷基)-环戊-2-烯-1-酮衍生物也是本发明的对象。
  • Method to evaluate fragrance compositions
    申请人:The Procter & Gamble Company
    公开号:EP2799864A1
    公开(公告)日:2014-11-05
    The present invention relates to a method to evaluate and profile a fragrance composition according to the associated biometric response in humans to the composition. A group of at least 20 test participants is exposed to at least 3 fragrance compositions and at least 4 biometric Autonomatic Nervous System (ANS) parameters are measured. Partition and random/bootstrap forest statistical analysis methods are applied to create a profiling model.
    本发明涉及一种根据人类对香味组合物的相关生物特征反应来评估和描述香味组合物的方法。一组至少 20 名测试参与者接触至少 3 种香味组合物,并测量至少 4 种生物特征自主神经系统(ANS)参数。应用分区和随机/自举森林统计分析方法来创建分析模型。
  • Capsule composition
    申请人:GIVAUDAN SA
    公开号:US10398632B2
    公开(公告)日:2019-09-03
    An encapsulated perfume composition for use in personal care products adapted to be applied to, and left on, the skin or hair of a human or animal subject, said encapsulated perfume composition comprising one or more polyurea capsules having a volume average diameter of 20 to 90 microns, and a capsule shell weight, which is 5 to 40% based on the total weight of the capsules.
    一种用于个人护理产品的封装香水组合物,适用于人或动物的皮肤或毛发,并可留在皮肤或毛发上,所述封装香水组合物包括一个或多个聚脲胶囊,其体积平均直径为 20 至 90 微米,胶囊外壳重量占胶囊总重量的 5 至 40%。
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