CAS: 459-80-3; Geranic Acid

该化合物是一种自然产生的不饱和脂肪酸,其特点是其长碳链和结构中存在双重结合.它是柑橘异构体,因其花粉和柑橘类芳香而闻名,在香味和口味行业中具有显著意义.Geranic酸一般是无色的,可溶于有机溶剂,但因其疏水性质,其溶解性在水中有限.该化合物的分子式反映其碳本体酸功能组,有助于其酸性和再活性.它也因其潜在的生物活动,包括抗微生物特性而备受注意,并研究其在各种生物化学途径中的作用.它的应用范围超越了化妆品和食品调味,因为它也可能作为其他有机化合物合成的前体.

结构式图片

相似化合物

106-24-1 106-25-2 5392-40-5

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ECHA物质C&L通报REACH预注册

上下游产品

(E/Z)-3,7-dimethyl-2,6-°Ctadienal (+/-)-3-hydroxy-3,7-dimethyl°Ct-6-enoic acid acetic anhydride ethyl 3,7-dimethyl-2,6-°Ctadienoateracemic citronellic acid 2,6-dimethyl-hepta-1,5-diene 3,7-dimethyl°Ctanoic acid 2,6-dimethyl-°Cta-2,6-dienedioic acid

合成工艺路线路线简述

  • 合成目标产物 Geranic Acid 主要起始原料 Lycopene
  • (文献来源)合成步骤主要原料 Lycopene
柠檬醛置于aldehyde Dehydrogenase From Pseudomonas Putida Kt2440,水,Nicotinamide Adenine Dinucleotide Phosphate体系中,化学反应生成 香叶酸
参考文献:对映选择性重排与加水结合:由α,β-不饱和醛直接合成对映体纯的饱和羧酸
标题:对映选择性重排与加水结合:由α,β-不饱和醛直接合成对映体纯的饱和羧酸
摘要:描述了一种新型的有机合成方法,该方法可将α,β-不饱和醛直接单锅转化为饱和羧酸.作为唯一的试剂,需要将水完全整合到产品中.该串联过程在理想的原子经济下进行,由两个耦合的氧化还原生物转化组成,而无需外部辅助底物进行辅因子再生.nadph依赖的烯还原酶催化α,β-不饱和醛的cc双键的初始还原,导致形成饱和醛和nadp +.然后将醛中间体氧化为相应的羧酸,从而为下一个催化循环再生nadph.当使用前手性α,β-不饱和醛作为底物时,相应的羧酸可对映体选择性地形成,其对映体选择性的分离度最高可达> 99%ee,如证明的那样,可用于将柠檬酸转化为(S)-香茅酸.
DOI:10.1002/cctc.201300764

海关参考信息

专利信息


专利号:WO-2009003796-A1
优先权日:2007-06-29
标 题:Method for the synthesis of neral by the isomerization of isocitrals
发明人:SCHMIDT-LEITHOFF JOACHIM; JAEKEL CHRISTOPH; PACIELLO ROCCO; HEYDRICH GUNNAR; HEIDEMANN THOMAS
权利人:BASF SE; SCHMIDT-LEITHOFF JOACHIM; JAEKEL CHRISTOPH; PACIELLO ROCCO; HEYDRICH GUNNAR; HEIDEMANN THOMAS
摘要:The present invention relates to a method for the synthesis of neral and/or geranial by the isomerization of one or more isocitrals. In particular, the invention relates to a method for the synthesis of neral in pure or enriched form, starting out from a mixture of materials containing neral and geranial and one or more isocitrals.

专利号:US-4064150-A
优先权日:1976-05-26
标 题 :Synthesis of isoprenoid 1,5-dienes
发明人:KATZENELLENBOGEN JOHN A
权利人:UNIV ILLINOIS
摘要:Aliphatic acids containing an isoprenoid 1,5-diene moiety are prepared in high yields by the selective gamma alkylation of α,β-unsaturated acids with allylic electrophiles. The gamma-regioselectivity of the alkylation is controlled by the use of the dicopper(I) dienolates prepared from the α,β-unsaturated acids. The method offers a particularly facile means for synthesizing isoprenoid 1,5-diene natural products such as farnesoic acid by alkylation of senecioic acid with geranyl bromide; geranoic acid by alkylation of senecioic acid with 3,3-dimethallyl bromide; and dl-lanceol by alkylation of tiglic acid with an allylic bromide derived from dl-limonene. Such products find use in the synthesis of insect pheremones, insect juvenile hormones, and components of perfumes.

专利号:US-2018105838-A1
优先权日:2015-03-11
标 题:Process for de novo microbial synthesis of terpenes
发明人:SCHRADER JENS; BUCHHAUPT MARKUS; SONNTAG FRANK; KRONER CORA; BRÜSER HEIKE; Schröder Hartwig; PELZER RALF
权利人:BASF SE
摘要:The invention relates to microbial terpene production. Known methods for microbial production of terpenes are mostly based on the direct conversion of sugars. Therefore alternative substrates, in particular alternative carbon sources, for use in microbial terpene production were desirable. The invention relates to a methylotrophic bacterium containing recombinant DNA coding for at least one polypeptide with enzymatic activity for heterologous expression in said bacterium, wherein said at least one polypeptide with enzymatic activity is selected from the group consisting an enzyme of a heterologous mevalonate pathway, a heterologous terpene synthase and optionally a heterologous synthase of a prenyl diphosphate precursor. The invention further relates in particular to a method for de novo microbial synthesis of sesquiterpenes or diterpenes from methanol and/or ethanol.

专利号:WO-2023247609-A1
优先权日:2022-06-22
标题 :Process for the preparation of cyclohomogeranates
发明人:SCHELWIES MATHIAS; BRUNNER BERNHARD; PELZER RALF; LIST BENJAMIN; TURBERG MATHIAS; MITSCHKE BENJAMIN; DAS SAYANTANI; DE CHANDRA KANTA
权利人:BASF SE; STUDIENGESELLSCHAFT KOHLE GGMBH
摘要:The present invention relates to a process for the preparation of cyclohomogeranates. The invention relates to the synthesis of cyclohomogeranates from well available esters of homogeranic acid in only one step. The cyclohomogeranates prepared according to the process of the present invention can be used in the fragrance industry as intermediates or the compounds can be used as such as aroma compound.

专利号:US-2022356497-A1
优先权日:2019-06-26
标 题 :Compositions and methods for synthesis of terpenoids
发明人:DE KOK STEFAN; LAU WARREN; MCSORLEY FERN; MEYER HERMANN-JOSEF; SERBER ZACH; WAWRZYN GRAYSON
权利人:ZYMERGEN INC
摘要:The disclosure relates to the biosynthesis of terpenoids, such as, for example, geraniol and derivatives thereof, using genetic engineering. In particular, the disclosure relates to the biosynthesis of nepetalactol, nepetalactone, dihydronepetalactone, and derivatives thereof. The disclosure provides recombinant cells genetically engineered to produce high levels of nepetalactol, nepetalactone and/or dihydronepetalactone. The disclosure also provides methods of producing nepetalactol, nepetalactone and dihydronepetalactone using cell-based systems as well as cell-free systems.

专利号:WO-2024227949-A1
优先权日:2023-05-04
标 题:Screening and uses of glutamine synthetase modulators
发明人:MARTINS GARCIA BRUNA; FARAH PERNAS LENA
权利人:MAX PLANCK GESELLSCHAFT
摘要:The present invention relates to an in vitro bioassay to identify glutamine synthetase activators and inhibitors on the basis of one or more glutamine markers such as citrate, a metabolite derived from the mevalonate pathway, a glutamine responsive mRNA or proteins, such as HMGCR or SREBP2. Disclosed herein are also glutamine synthetase activators and inhibitors identified by the inventive method for use to stimulate or inhibit the synthesis of a metabolite derived from the mevalonate pathway, such as cholesterol, and to treat a disease associated with deregulated levels of said metabolite, such as cancer.
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主要参考文献


1: Tanner EEL, Curreri AM, Balkaran JPR, Selig-Wober NC, Yang AB, Kendig C, Fluhr MP, Kim N, Mitragotri S. Design Principles of Ionic Liquids for Transdermal Drug Delivery. Adv Mater. 2019 Jul;31(27):e1901103. doi: 10.1002/adma.201901103. Epub 2019 May 21. doi: 10.1021/acs.jafc.8b04395. Epub 2018 Nov 12. doi: 10.1016/j.fct.2018.08.022. Epub 2018 Aug 16. Review. doi: 10.1016/j.jconrel.2018.07.029. Epub 2018 Jul 17. doi: 10.1073/pnas.1722338115. Epub 2018 Jun 25.
6: Kries H, Kellner F, Kamileen MO, O'Connor SE. Inverted stereocontrol of iridoid synthase in snapdragon. J Biol Chem. 2017 Sep 1;292(35):14659-14667. doi: 10.1074/jbc.M117.800979. Epub 2017 Jul 12.
7: Haruehanroengra P, Vangaveti S, Ranganathan SV, Wang R, Chen A, Sheng J. Nature's Selection of Geranyl Group as a tRNA Modification: The Effects of Chain Length on Base-Pairing Specificity. ACS Chem Biol. 2017 Jun 16;12(6):1504-1513. doi: 10.1021/acschembio.7b00108. Epub 2017 Apr 18. doi: 10.1038/ncomms11035.

合成参考文献


摘要:Hollmann, F., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 3, 122.
摘要:Biochemical Journal., 34(1196), 1940
参考文献:10.1016/s0960-894x(02)00038-0
摘要:Kim S, Kim E, Shin DS, Kang H, Oh KB. Evaluation of morphogenic regulatory activity of farnesoic acid and its derivatives against Candida albicans dimorphism. Bioorg Med Chem Lett. 2002 Mar 25;12(6):895–8. doi: 10.1016/s0960-894x(02)00038-0.
参考文献:10.1007/s00253-020-10811-9
摘要:Weimer A, Kohlstedt M, Volke DC, Nikel PI, Wittmann C. Industrial biotechnology of Pseudomonas putida: advances and prospects. Applied Microbiology and Biotechnology. 2020 Aug 13;104(18):7745–66. doi: 10.1007/s00253-020-10811-9.
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