(2E,8E)-8-hydroxy-3,7-dimethyl-2,6-octadienal | 80054-37-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2E,8E)-8-hydroxy-3,7-dimethyl-2,6-octadienal
• 英文别名: 10-hydroxygeranial；(6E)-8-hydroxygeranial；(2E,6E)-8-hydroxy-3,7-dimethylocta-2,6-dienal
• CAS: 80054-37-1
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: WTWGQWLNUNSMGM-TXFIJWAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,8E)-8-hydroxy-3,7-dimethyl-2,6-octadienal 生成 (2E,6E)-1-deuterio-3,7-dimethylocta-2,6-diene-1,8-diol
  参考文献：
  名称：

  IKEDA, HIROMITSU;NAKAI, SHUNJI;HASHIMOTO, KEIJI;UESATO, SHINICHI;ESAKI, N+, PHYTOCHEMISTRY, 30,(1991) N, C. 2223-2225

  摘要：

  DOI：
• 作为产物：
  描述：

  8-hydroxygeranyl acetate 在 manganese(IV) oxide 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 56.0h， 生成 (2E,8E)-8-hydroxy-3,7-dimethyl-2,6-octadienal
  参考文献：
  名称：

  The aphid sex pheromone cyclopentanoids: Synthesis in the elucidation of structure and biosynthetic pathways

  摘要：

  Identification of a range of aphid sex pheromones as comprising the cyclopentanoids (4aS,7S,7aR)-nepetalactune, (1R,4aS,7S,7aR)-nepetalactol and the (1S)- and (1R,4aR,7S,7aS)-nepetalactols required samples authenticated by H-1 and C-13 NMR. These and related compounds were provided by small scale synthesis and extraction from plants in the genus Nepeta (Lamiaceae). The subsequent discovery that the synthetic sex pheromones could attract males, and also parasitic wasps that attack aphids, has created a need for large scale syntheses of the cyclopentanoids. This is afforded by cyclisation of the 8-oxo-1-enamine of citronellal as originally developed by Schreiber and co-workers (1986). Investigation into the biosynthesis of the cyclopentanoids by plants for exploiting aphid sex pheromones in crop protection by means of molecular biology required synthesis of putative biosynthetic intermediates, some with radioactive isotopic labelling, particularly 8-oxidised monoterpene alcohols and aldehydes. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00012-0

文献信息

• PROCESS FOR THE PRODUCTION OF 2,6-DIMETHYLHEPT-5-ENAL BY BAEYER-VILLIGER OXIDATION
  申请人：GIVAUDAN SA

  公开号：US20160318836A1

  公开（公告）日：2016-11-03

  Disclosed is a process for the production of 2,6-dimethylhept-5-enal by Baeyer-Villiger oxidation of 3,7-dimethylocta-2,6-dienal in the presence of aqueous H 2 O 2 and SeO 2 , followed by hydrolysis.

  揭示了一种通过在水合过氧化氢和二氧化硒存在下对3,7-二甲基辛二烯醛进行巴耶-维利格氧化，随后进行水解制备2,6-二甲基庚-5-烯醛的过程。
• [EN] PROCESS<br/>[FR] PROCÉDÉ
  申请人：GIVAUDAN SA

  公开号：WO2016054797A1

  公开（公告）日：2016-04-14

  Disclosed is a process for the production of 2, 6-dimethylhept-5-enal by Baeyer-Villiger oxidation of 3, 7-dimethylocta-2, 6-dienal in the presence of potassium peroxymonosulfate suspended in a solvent selected followed by hydrolysis.

  公开了一种通过在选择的溶剂中使用过氧单硫酸钾进行Baeyer-Villiger氧化3,7-二甲基辛二烯醛制备2,6-二甲基庚-5-烯醛的方法，随后进行水解。
• [EN] PROCESS FOR THE PRODUCTION OF 2,6-DIMETHYLHEPT-5-ENAL BY BAEYER-VILLIGER OXIDATION<br/>[FR] PROCÉDÉ DE PRODUCTION DE 2,6-DIMÉTHYLHEPT-5-ÉNAL PAR OXYDATION DE BAEYER-VILLIGER
  申请人：GIVAUDAN SA

  公开号：WO2015110505A1

  公开（公告）日：2015-07-30

  Disclosed is a process for the production of 2,6-dimethylhept-5-enal by Baeyer-Villiger oxidation of 3,7-dimethylocta-2,6-dienal in the presence of aqueous H2O2 and SeO2, followed by hydrolysis.

  本发明揭示了一种通过在水合H2O2和SeO2存在下，将3,7-二甲基辛-2,6-二烯醛进行巴耶-维利格氧化，然后进行水解，生产2,6-二甲基庚-5-烯醛的方法。
• Elucidation of iridodial formation mechanism - partial purification and characterization of the novel monoterpene cyclase from cell suspension cultures
  作者：Shinichi Uesato、Hiromitsu Ikeda、Tetsuro Fujita、Hiroyuki Inouye、Meinhart H. Zenk

  DOI：10.1016/s0040-4039(00)96530-4

  日期：1987.1

  From the incubation system of 10-hydroxygeraniol and crude enzyme extracts from cell suspension cultures, 10-oxogeraniol, 10-hydroxygeranial and 10-oxogeranial were isolated. A precursory role in the biosynthesis of iridodial has been demonstrated for these three compounds. This fact unequivocally substantiates our previous claim for the biosynthesis of iridodial. In addition, a novel monoterpene cyclase

  从10-羟基香叶醇和细胞悬浮培养物的粗酶提取物的培养系统中，分离出10-氧香叶醇，10-羟基香叶醛和10-氧香叶醛。对于这三种化合物，已证明在铱的生物合成中具有先驱作用。这一事实明确地证实了我们先前对虹膜二代生物合成的主张。另外，部分纯化并表征了催化虹彩形成的新型单萜环化酶。
• Coexpression Analysis Identifies Two Oxidoreductases Involved in the Biosynthesis of the Monoterpene Acid Moiety of Natural Pyrethrin Insecticides in <i>Tanacetum cinerariifolium</i>
  作者：Haiyang Xu、Gaurav D. Moghe、Krystle Wiegert-Rininger、Anthony L. Schilmiller、Cornelius S. Barry、Robert L. Last、Eran Pichersky

  DOI：10.1104/pp.17.01330

  日期：2018.1

  of either trans-chrysanthemic acid or its modified form, pyrethric acid, and one of three alcohols, jasmolone, pyrethrolone, and cinerolone, that appear to be derived from jasmonic acid. Chrysanthemyl diphosphate synthase (CDS), the first enzyme involved in the synthesis of trans-chrysanthemic acid, was characterized previously and its gene isolated. TcCDS produces free trans-chrysanthemol in addition

  食草艾草的花产生了一组统称为除虫菊酯的化合物，这是商业上重要的农药，对飞行的昆虫有强烈的毒性，但对大多数脊椎动物没有毒性。拟除虫菊酯分子是一种酯，它由反菊糖酸或其修饰形式，除虫菊酸和三种醇（茉莉酮，除虫菊酯和肉桂酮）中的一种组成，它们似乎是从茉莉酸衍生而来的。菊酯二磷酸合酶（CDS）是第一个参与反菊酸合成的酶，此前已进行了表征并分离了其基因。TcCDS除反式菊二磷酸酯外还产生游离的反式菊糖，但尚未报道负责将反式菊糖转化为相应的醛然后转化为酸的酶。我们使用基于RNA测序的方法和共表达相关性分析来鉴定编码推定的反式菊花和反式菊花脱氢酶的几种候选基因。我们使用体外生化分析和植物中的异源表达相结合的方法，对这些基因编码的蛋白质进行了功能鉴定，以证明TcADH2编码一种将反式菊花转化为反式菊花的酶，而TcALDH1编码的一种将氧化式菊花转化成的酶。反式菊苣酸。TcADH2和TcALDH1与TcCDS