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甲基茉莉酸酯 | 1101843-02-0

中文名称
甲基茉莉酸酯
中文别名
甲基茉莉酸酯(异构体的混和物)
英文名称
methyl jasmonate
英文别名
(+)-methyl (R,Z)-cis-3-oxo-2-(2-pentenyl)-1-cyclopentaneacetate;(Z)-methyl 2-(3-oxo-2-(pent-2-en-1-yl)cyclopentyl)acetate;methyl {3-oxo-2-[(2Z)-2-pentenyl]cyclopentyl}acetate;(Z)-methyl jasmonate;methyljasmonate;3-methoxycarbonylmethyl-2-(cis-2'-pentenyl)-cyclopentanone;methyl {3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl}acetate;methyl 2-[3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetate
甲基茉莉酸酯化学式
CAS
1101843-02-0
化学式
C13H20O3
mdl
——
分子量
224.3
InChiKey
GEWDNTWNSAZUDX-PLNGDYQASA-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

物化性质

  • 沸点:
    96°C/2.7mmHg(lit.)
  • 密度:
    1.003±0.06 g/cm3(Predicted)
  • 闪点:
    156°C(lit.)
  • 物理描述:
    Colourless oily liquid; Powerful floral-herbaceous, sweet aroma
  • 颜色/状态:
    Colorless liquid
  • 气味:
    Sharp persistent odor
  • 溶解度:
    In water, 340 mg/L at 25 °C (est)
  • 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:
    1684.5

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,产生了叠加效应。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。细胞外蛋白组分析显示存在与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,其他PR蛋白在C. annuum的对照和激发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、胞间CO2浓度和总叶绿素含量。相比之下,叶面喷施MeJA提高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...在受胁迫的植物上施用MeJA减少了脂质过氧化物的产生,并刺激了抗氧化酶的合成,从而提高了青蒿素的含量和产量。因此,可以得出结论,MeJA可能被用于减轻硼毒害,并提高A. annua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)连续冲洗每只眼睛……。不要使用催吐剂。对于摄入,如果患者能吞咽、有强烈的呕吐反射且不流口水,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

  • 储存条件:
    室温且干燥

制备方法与用途

茉莉酮酸类[植物生长调节剂]

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 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:
    甲基茉莉酸酯盐酸potassium permanganate 作用下, 以 四氯化碳 为溶剂, 反应 2.0h, 生成 MJS81f13
    参考文献:
    名称:
    [EN] JASMONATE DERIVATIVE COMPOUNDS, PHARMACEUTICALS COMPOSITIONS AND METHODS OF USE THEREOF
    [FR] COMPOSES DERIVES DE JASMONATE, COMPOSITIONS PHARMACEUTIQUES ET METHODES D'UTILISATION ASSOCIEES
    摘要:
    公开号:
    WO2005054172A3
  • 作为产物:
    参考文献:
    名称:
    [EN] METHODS FOR PREPARATION OF JASMONATE COMPOUNDS
    [FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS DE JASMONATE
    摘要:
    这项发明涉及通过茉莉酸盐制备茉莉酸酯化合物的方法。
    公开号:
    WO2019135243A1
  • 作为试剂:
    描述:
    methyl cucurbic acid铬酸乙酸乙酯氯化钠 、 silica gel 、 甲基茉莉酸酯 作用下, 以 二氯甲烷 为溶剂, 18.0 ℃ 、47.99 kPa 条件下, 反应 12.0h, 以affording 3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanone (compound (4), R2 =CH3) in a yield of 88%, b.p. 92°-96° C./2.7 mm Hg的产率得到甲基茉莉酸酯
    参考文献:
    名称:
    Process for preparing 2-cyclopentenone derivative and perfume
    摘要:
    一种制备式为##STR1##的2-环戊酮衍生物的方法,其中A为##STR2##,R.sub.2为较低的直链或支链烷基,烯基或芳基烷基,并且含有该衍生物的香水组合物。
    公开号:
    US04237308A1
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文献信息

  • Jasmonoid Synthesis from<i>sci</i>-4-Heptenoic Acid
    作者:Toshio Sato、Tatsuo Kawara、Kazumi Sakata、Tamotsu Fujisawa
    DOI:10.1246/bcsj.54.505
    日期:1981.2
    Jasmonoids with cis-2-pentenyl side chain such as cis-jasmone, methyl jasmonate, and jasmolone were easily synthesized from cis-4-heptenoic acid obtained by the ring opening reaction of β-propiolactone with di-cis-butenylcuprate.
    通过β-丙内酯与二-顺-丁烯基铜酸盐的开环反应获得的顺-4-庚烯酸可以很容易地合成具有顺-2-戊烯基侧链的茉莉酮类化合物,如顺-茉莉酮、茉莉酸甲酯和茉莉酮酮。
  • Highly Selective Hydrogenation of Carbon-Carbon Multiple Bonds Catalyzed by the Cation [(C<sub>6</sub>Me<sub>6</sub>)<sub>2</sub>Ru<sub>2</sub>(PPh<sub>2</sub>)H<sub>2</sub>]<sup>+</sup>: Molecular Structure of [(C<sub>6</sub>Me<sub>6</sub>)<sub>2</sub>Ru<sub>2</sub>(PPh<sub>2</sub>)(CHCHPh)H]<sup>+</sup>, a Possible Intermediate in the Case of Phenylacetylene Hydrogenation
    作者:Mathieu J.-L. Tschan、Georg Süss-Fink、Frédéric Chérioux、Bruno Therrien
    DOI:10.1002/chem.200600576
    日期:2007.1
    been studied as the catalyst for the hydrogenation of carbon-carbon double and triple bonds. In particular, [1][BF(4)] turned out to be a highly selective hydrogenation catalyst for olefin functions in molecules also containing reducible carbonyl functions, such as acrolein, carvone, and methyljasmonate. The hypothesis of molecular catalysis by dinuclear ruthenium complexes is supported by catalyst-poisoning
    研究了双核阳离子[(C(6)Me(6))(2)Ru(2)(PPh(2))H(2)](+)(1)作为碳-碳氢化的催化剂碳双键和三键。尤其是,[1] [BF(4)]被证明是一种对烯烃功能具有高选择性的加氢催化剂,该分子还含有可还原的羰基官能团,例如丙烯醛,香芹酮和茉莉酮酸甲酯。催化剂中毒实验,环己烯加氢动力学中没有诱导期,以及阳离子四氟硼酸盐的分离和单晶X射线结构分析支持了双核钌配合物进行分子催化的假说。 (C(6)Me(6))(2)Ru(2)(PPh(2))(CHCHPh)H](+)(2),在苯乙炔氢化的情况下,可以认为是中间体。根据这些发现,
  • 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。
  • Synthesis, structural characterization and biological activity of two diastereomeric JA-Ile macrolactones
    作者:Guillermo H. Jimenez-Aleman、Ricardo A. R. Machado、Helmar Görls、Ian T. Baldwin、Wilhelm Boland
    DOI:10.1039/c5ob00362h
    日期:——
    the potential biological activities of 12-modified JA-Ile derivatives, we synthesized two macrolactones (JA-Ile-lactones (4a) and (4b)) derived from 12-OH-JA-Ile (3). The biological activity of (4a) and (4b) was tested for their ability to elicit nicotine production, a well-known jasmonate dependent secondary metabolite. Both macrolactones showed strong biological activity, inducing nicotine accumulation
    茉莉酸盐是植物激素,涉及许多植物过程,包括生长,发育,衰老和防御。Jasmonoyl-大号-异亮氨酸(JA-ILE,2),氨基茉莉酸的共轭酸(JA,1),已被鉴定为生物活性内源性茉莉酮酸。然而,JA-Ile(2)类似物在植物中触发了不同的响应。戊烯基侧链的ω-羟基氧化导致失活的12-OH-JA-Ile(3)充当“终止”信号。另一方面,尽管没有已知的生物学功能,但是自然界中存在12-OH-JA(5)的内酯衍生物(茉莉酮内酯,JKL)。受到JKL化学结构的启发(6),并为了进一步探索12-修饰的JA-Ile衍生物的潜在生物活性,我们合成了两种大内酯(JA-Ile-内酯(4a)和(4b)),它们衍生自12-OH-JA-Ile(3)。 。对(4a)和(4b)的生物活性进行了测试,以激发它们产生烟碱的能力,烟碱是众所周知的依赖于茉莉酸酯的次生代谢产物。两个大环内酯显示出很强的生物活性,诱导烟碱积累作
  • Partial Syntheses of Methyl Dehydrojasmonate and Tuberolactone
    作者:Paul Dubs、Rita Stüssi
    DOI:10.1002/hlca.19780610308
    日期:1978.4.19
    The natural products methyl dehydrojasmonate (1) and tuberolactone (2) have been synthesized from methyl jasmonate (3) and jasmolactone (4) resp., via sulfenylation-sulfoxide pyrolysis.
    天然产物甲基dehydrojasmonate(1)和tuberolactone(2)从茉莉酮酸甲酯(已被合成3)和jasmolactone(4)RESP。,经由亚磺酰亚砜热解。
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