CAS: 4638-92-0; (+)-Trans-Chrysanthemic Acid

该化合物是一种单环碳酸,因其在合成除虫菊杀虫剂过程中作为关键中间体的作用而得到广泛承认,其立体(+)变性能确保化学变异的高度回动性和选择性,使其对生产生物活性化合物具有价值;该化合物具有极强的稳定性和纯度,有利于农业化学研究与开发的精确应用;其结构特性有利于高效衍生,能够产生高效和减少环境影响的强效杀虫剂. (+) 转基因菊酯酸在实验室和工业环境中普遍使用,其一贯质量和可靠性能支持先进的合成工作流程.

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2259-14-5 2935-23-1 97-41-6

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CAS号27335-32-6 methyl 2,2-dime... | CAS号5460-63-9 菊酸甲酯

合成工艺路线路线简述

    📜茉酮菊素ⅰ置于氢氧化钾体系中,用 乙醇 作为反应溶剂,化学反应生成 (+)-反式-菊酸
    参考文献:(S)-生物丙烯菊酯和相关化合物在人体中的代谢
    标题:(S)-生物丙烯菊酯和相关化合物在人体中的代谢
    摘要:菊花类杀虫剂,如 (S)-生物丙烯菊酯,天然除虫菊酯和相关拟除虫菊酯,在哺乳动物代谢过程中会发生广泛的水解和氧化变性,导致一系列复杂的代谢物部分结合并最终在尿液中消除.合成了菊酸的主要氧化产物顺式-(E)-和反式-(E)-菊花二羧酸(顺式-(E)和反式-(E)-Cdca),并通过核磁共振确定了它们的结构光谱法 (H1-NMR) 和质谱法 (Ms).非对映选择性分离通过高效液相色谱 (HPLC) 和毛细管气相色谱 (Gc) 进行.开发了一种从人尿中提取和鉴定 Cdca 的分析方法.通过气相色谱法和电子冲击质谱法 (Gc/ms) 进行定量.顺式-(E)-Cdca 的检测限为 20 微克/升,反式 (E)-Cdca 的检测限为 10 微克/升.为了测试所提出方法的适用性,研究了暴露于 (S)-生物丙烯菊酯的人类尿液样本.暴露后 24 小时内出现反式-(E)-Cdca 的尿液排泄峰值.
    DOI:10.1016/s0378-4274(99)00038-7

    海关参考信息

    专利信息


    专利号:US-10647655-B2
    优先权日:2016-09-02
    标题:Method for the synthesis of permethrin
    发明人:PULLAGURLA MANIK REDDY; NANDA KUMAR MECHERIL VALSAN; VELIGETLA MADHUSUDHANA RAO; RANGISETTY JAGADEESH BABU
    权利人:BIOPHORE INDIA PHARMACEUTICALS PVT LTD
    摘要:An improved method for the synthesis of substantially pure Permethrin having purity greater than 99.5% by Gas Chromatography provided. The embodiments also relates to a purification process of Permethrin by recrystallization from methanol-water mixture.

    专利号:US-7723539-B2
    优先权日:2004-06-16
    标题:Catalysts based on metal complexes for the synthesis of optically active chrysanthemic acid
    发明人:CARLONI SILVIA; BORZATTA VALERIO; MORONI LENI; TANZI GIADA; SARTORI GIOVANNI; MAGGI RAIMONDO
    权利人:ENDURA SPA
    摘要:Catalysts are described based on metal complexes derived from optically active s compounds, chosen from the classes consisting of bisoxazolines and salicylaldimines supported on an organic or inorganic matrix and employed in particular for the synthesis of optically active chrysanthemic acid.

    专利号:US-4749797-A
    优先权日:1983-04-08
    标题 :Tetra-alkyl-2,2,5,5-cyclohexanone-4-01-1 compounds and their sulphonyl derivatives, the process and the intermediates for preparing them and their use in the synthesis of cis-cyclopropane lactones
    发明人:D ANGELO JEAN; REVIAL GILBERT; AZERAD ROBERT; BUISSON DIDIER
    权利人:ROUSSEL UCLAF
    摘要:New tetra-alkyl-2,2,5,5-cyclohexanone-4-ol-1-compounds and their sulphonyl derivatives with the general formula: ##STR1## in which: each of R and R', identical or different, represents an alkyl radical (1-5 carbons) and R' represents a hydrogen atom or a radical SO 2 R'' in which R'' represents an alkyl radical (1-5 carbons) or an aryl radical (6-14 carbons), the process and the intermediates for their preparation, as well as their use in the synthesis of cyclopropane lactones of cis structure.

    专利号:WO-9216499-A1
    优先权日:1991-03-13
    标 题 :General synthesis method by photochemical process of cyclopropanic components present in natural pyrethrines and in synthetic pyrethroids and their 1-aza-1,4,6 trianic precursors
    发明人:ARMESTO VILAS DIEGO; GOMEZ GALLEGO MAR; HORSPOOL WILLIAM M; BERMEJO TORRES FERNANDO
    权利人:UNIV MADRID COMPLUTENSE
    摘要:The present invention relates to the synthesis of 2,2-dimethyl-3-(vinyl-2,2-bi-substituted) cyclopropanocarboxylic acids. Said acids are present in the majority of natural pyrethrines and in synthetic pyrethroids. These acids are obtained by the transposition reaction aza-di-Ï€-methane of a 1-aza-1,4,6-trianic system for which there are disclosed three different synthetic processes. Thereby, precursors are available to obtain pyrethrines and pyrethroids, obtained by a direct and simple process with a high yield.

    专利号:US-5443978-A
    优先权日:1993-03-11
    标 题 :Chrysanthemyl diphosphate synthase, corresponding genes and use in pyrethrin synthesis
    发明人:ELLENBERGER SUZANNE R; PEISER GALEN D; BELL RUSSELL N; HUSSEY JR CHARLES E; SHATTUCK-EIDENS DONNA M; SWEDLUND BRADLEY D
    权利人:AGRIDYNE TECH INC
    摘要:This invention provides a purified chrysanthemyl diphosphate synthase (CDS), a method for the purification of CDS from Chrysanthemum cinerariaefolium, and an amino acid sequence of the isolated CDS. Also provided is a cDNA encoding the CDS, a nucleotide sequence of the CDS gene, and a derived amino acid sequence of the encoded CDS protein. The CDS gene is useful in the enzymatic production of the natural stereospecific configuration of chrysanthemyl derivatives which are useful for the synthesis of pyrethrins, pyrethroids, derivatives thereof, as well as other classes of metabolites.

    专利号:US-3894916-A
    优先权日:1972-09-07
    标题 :Separation of 3,3-dimethylacrolein and -methyl-3-buten-1-ol by azeotropic distillation with water and glycerol
    发明人:FISCHER ROMAN; MAIER SIEGFRIED; KOERNIG WOLFGANG
    权利人:BASF AG
    摘要:A process for separating, by distillation, a mixture consisting essentially of 3,3-dimethylacrolein and 3-methyl-3-buten-1-ol, wherein the mixture to be separated is distilled in the presence of water and glycerol, the 3,3-dimethyl-acrolein first being distilled off azeotropically with water and the 3-methyl-3-buten1-ol then being separated, as an azeotropic mixture with water, from the higher-boiling glycerol. It is also possible to isolate the 3,3-dimethylacrolein by distillation if the 3-methyl-3-buten1-ol is partially replaced by 3-methyl-2-buten-1-ol. The 3,3dimethylacrolein, which can be isolated in pure form by the process of the invention, is a valuable intermediate for the synthesis of natural substances such as citral, vitamin A and chrysanthemic acid.

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    主要参考文献

    [参考文献]: A I Gurova, Et Al. [参考文献]: Gig Tr Prof Zabol. 1987 Jul:(7):53-4.
    [参考文献]: A I Gurova, Et Al. [参考文献]: Gig Sanit. 1986 Jan:(1):16-8.
    [参考文献]: Aldana M Ramirez, Et Al. Bidirectional Secretions From Glandular Trichomes Of Pyrethrum Enable Immunization Of Seedlings. Plant Cell. 2012 Oct;24(10):4252-65.
    [参考文献]: Alec C Gerry, Et Al. Low Pilot Exposure To Pyrethrin During Ultra-Low-Volume (Ulv) Aerial Insecticide Application For Control Of Adult Mosquitoes. J Am Mosq Control Assoc. 2005 Sep;21(3):291-5.
    [参考文献]: K Mitsukura, Et Al. Characteristics And Function Of Alcaligenes Sp. Nbrc 14130 Esterase Catalysing The Stereo-Selective Hydrolysis Of Ethyl Chrysanthemate. J Appl Microbiol. 2010 Apr;108(4):1263-70.

    合成参考文献


    摘要:S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759
    摘要:Journal of Agricultural and Food Chemistry., 22(212), 1974 []
    摘要:Pesticide Biochemistry and Physiology., 6(491), 1976
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