(E)-9-甲酰基-2-烯酸 | 172759-80-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (E)-9-甲酰基-2-烯酸
• 英文名称: (E)-9-formylnon-2-enoic acid
• 英文别名: 10-Oxo-decenoic acid；(E)-10-oxodec-2-enoic acid
• CAS: 172759-80-7
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: GQNUOWMXNITYLS-SOFGYWHQSA-N

物化性质

• 沸点：
  346.3±35.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-9-甲酰基-2-烯酸 在 sodium hydroxide 、 sodium tetrahydroborate 、 盐酸 作用下， 以 水 、 甲醇 、 乙醚 为溶剂， 生成 10-羟基-2-癸烯酸
  参考文献：
  名称：

  Lithiated anions derived from (alkenyl)pentamethyl phosphoric triamides: Useful synthons for the stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of queen substance and royal jelly of honeybee Apis mellifera

  摘要：

  Lithiated anions derived from (alkenyl) pentamethyl phosphoric triamides as homoenolate equivalents are used in the reaction with halogenated acetal and ketal giving regioselectively the gamma-alkylation adducts. Chemoselective acidic hydrolysis of the enephosphoramide moiety in the presence of acetal or ketal groups leads to expected carbonyl products, key intermediates in the synthesis of natural compounds. The synthetic potential of the presented strategy is illustrated by stereoselective synthesis of two pheromones namely, 9-oxo-2(E)-decenoic acid 1 from queen substance and 10-hydroxy-2(E)-decenoic acid 2 from royal jelly of honeybee Apis mellifera. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.06.020
• 作为产物：
  描述：

  (E)-9-(1,3-dioxolan-2-yl)non-2-enoic acid 在 盐酸 、 水 作用下， 反应 4.0h， 生成 (E)-9-甲酰基-2-烯酸
  参考文献：
  名称：

  Lithiated anions derived from (alkenyl)pentamethyl phosphoric triamides: Useful synthons for the stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of queen substance and royal jelly of honeybee Apis mellifera

  摘要：

  Lithiated anions derived from (alkenyl) pentamethyl phosphoric triamides as homoenolate equivalents are used in the reaction with halogenated acetal and ketal giving regioselectively the gamma-alkylation adducts. Chemoselective acidic hydrolysis of the enephosphoramide moiety in the presence of acetal or ketal groups leads to expected carbonyl products, key intermediates in the synthesis of natural compounds. The synthetic potential of the presented strategy is illustrated by stereoselective synthesis of two pheromones namely, 9-oxo-2(E)-decenoic acid 1 from queen substance and 10-hydroxy-2(E)-decenoic acid 2 from royal jelly of honeybee Apis mellifera. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.06.020

文献信息

• Production of food flavor-acceptable jasmonic acid and methyl jasmonate by Diplodia gossypina
  申请人：INTERNATIONAL FLAVORS & FRAGRANCES INC.

  公开号：EP1118672A2

  公开（公告）日：2001-07-25

  Described is a bioprocess for the high-yield production of food flavor-acceptable jasmonic acid and methyl jasmonate, as well as a novel jasmonic acid isomer produced thereby and organoleptic uses thereof. The process yields at least 5% of the "cis" isomer defined according the structure: (wherein R is hydrogen or methyl) or at least 5% of the "cis" isomer defined according to the structure: (wherein R is hydrogen or methyl). Compositions containing at least 98% of the isomer having the structure: with an optical rotation (α20D) of +58° are novel. Compositions containing at least 98% of the isomer having the structure: with an optical rotation (α20D) of +58° are also novel. The process of our invention comprises the cultivation under aerobic condition of one or more specific strain of Diplodia gossypina in a nutrient medium followed either by (1) isolation of the jasmonic acid product or (2) esterification of the jasmonic acid to form methyl jasmonate followed by the isolation of the methyl jasmonate and novel products produced by such process.

  描述了一种高产生产可接受食品风味的茉莉酸和茉莉酸甲酯的生物工艺，以及由此生产的一种新型茉莉酸异构体及其感官用途。该工艺可获得至少 5%的按以下结构定义的 "顺式 "异构体： (其中 R 为氢或甲基）或至少 5%根据以下结构定义的 "顺式 "异构体： (其中 R 为氢或甲基）。含有至少 98%具有以下结构的异构体的组合物： 旋光度 (α20D) 为 +58° 的异构体的组合物是新颖的。含有至少 98%具有以下结构的异构体的化合物 光学旋转（α20D）为 +58° 的异构体的含量至少为 98% 的组合物也是新颖的。本发明的工艺包括在有氧条件下，在营养培养基中培养一株或多株Diplodia gossypina的特定菌株，然后(1)分离茉莉酸产物或(2)将茉莉酸酯化形成茉莉酸甲酯，然后分离茉莉酸甲酯和由该工艺产生的新型产物。
• Bioprocess for the high-yield production of food flavor-acceptable jasmonic acid and methyl jasmonate, novel jasmonic acid isomer produced thereby and uses thereof
  申请人：——

  公开号：US20020110881A1

  公开（公告）日：2002-08-15

  Described is a bioprocess for the high-yield production of food flavor-acceptable jasmonic acid and methyl jasmonate, as well as a novel jasmonic acid isomer produced thereby and organoleptic uses thereof. The process yields at least 5% of the “cis” isomer defined according the structure: 1 (wherein R is hydrogen or methyl) or at least 5% of the “cis” isomer defined according to the structure: 2 (wherein R is hydrogen or methyl). Compositions containing at least 98% of the isomer having the structure: 3 with an optical rotation (&agr; D 2 ) of +58° are novel. Compositions containing at least 98% of the isomer having the structure: 4 with an optical rotation (&agr; D 20 ) of +58° are also novel. The process of our invention comprises the cultivation under aerobic condition of one or more specific strain of Diplodia gossypina in a nutrient medium followed either by (1) isolation of the jasmonic acid product or (2) esterification of the jasmonic acid to form methyl jasmonate followed by the isolation of the methyl jasmonate and novel products produced by such process.

  描述了一种高产生产可接受食品风味的茉莉酸和茉莉酸甲酯的生物工艺，以及由此生产的一种新型茉莉酸异构体及其感官用途。该工艺可生产至少 5%的按结构定义的 "顺式 "异构体： 1 (其中 R 为氢或甲基）或至少 5%根据结构定义的 "顺式 "异构体： 2 (其中 R 为氢或甲基）。含有至少 98%具有以下结构的异构体的组合物： 3 具有旋光性（&agr； D 2 )为 58°的异构体是一种新型物质。含有至少 98% 的具有以下结构的异构体的组合物： 4 的异构体，其旋光性（&agr； D 20 ）为 58°的异构体也是新颖的。本发明的工艺包括在有氧条件下培养一株或多株特定的 Diplodia gossypina (1)分离出茉莉酸产品或(2)将茉莉酸酯化形成茉莉酸甲酯，然后分离出茉莉酸甲酯和由该工艺产生的新产品。
• Bioprocess for the high-yield production of food flavor-accaptable jasmonic acid and methyl jasmonate, novel jasmonic acid isomer produced thereby and uses thereof
  申请人：——

  公开号：US20030186399A1

  公开（公告）日：2003-10-02

  Described is a bioprocess for the high-yield production of food flavor-acceptable jasmonic acid and methyl jasmonate, as well as a novel jasmonic acid isomer produced thereby and organoleptic uses thereof. The process yields at least 5% of the “cis” isomer defined according the structure: 1 (wherein R is hydrogen or methyl) or at least 5% of the “cis” isomer defined according to the structure: 2 (wherein R is hydrogen or methyl). Compositions containing at least 98% of the isomer having the structure: 3 with an optical rotation (&agr; D 20 ) of +58° are novel. Compositions containing at least 98% of the isomer having the structure: 4 with an optical rotation (&agr; D 20 ) of +58° are also novel. The process of our invention comprises the cultivation under aerobic condition of one or more specific strain of Diplodia gossypina in a nutrient medium followed either by (1) isolation of the jasmonic acid product or (2) esterification of the jasmonic acid to form methyl jasmonate followed by the isolation of the methyl jasmonate and novel products produced by such process.

  描述了一种高产生产可接受食品风味的茉莉酸和茉莉酸甲酯的生物工艺，以及由此生产的一种新型茉莉酸异构体及其感官用途。该工艺可生产至少 5%的按结构定义的 "顺式 "异构体： 1 (其中 R 为氢或甲基）或至少 5%根据结构定义的 "顺式 "异构体： 2 (其中 R 为氢或甲基）。含有至少 98%具有以下结构的异构体的组合物： 3 具有旋光性（&agr； D 20 )为 58°的异构体是一种新型物质。含有至少 98% 的具有以下结构的异构体的组合物： 4 的异构体，其旋光性（&agr； D 20 ）为 58°的异构体也是新颖的。本发明的工艺包括在有氧条件下培养一株或多株特定的 Diplodia gossypina (1)分离出茉莉酸产品或(2)将茉莉酸酯化形成茉莉酸甲酯，然后分离出茉莉酸甲酯和由该工艺产生的新产品。
• Novel cytochrome P450 monooxygenase
  申请人：McGonigle Brian

  公开号：US20060156430A1

  公开（公告）日：2006-07-13

  This invention relates to an isolated polynucleotide encoding a cytochrome P450 monooxygenase that in the presence of linoleic acid results in production of 1-octen-3-ol. The invention also relates to the construction of a recombinant DNA construct comprising all or a portion of the polynucleotide encoding the cytochrome P450 monooxygenases of the invention, in sense or antisense orientation, wherein expression of the recombinant DNA construct results in production of altered levels 1-octen-3-ol in a transformed host cell.

  本发明涉及一种分离的多核苷酸，该多核苷酸编码一种细胞色素 P450 单加氧酶，该酶在亚油酸存在下可产生 1-辛烯-3-醇。本发明还涉及重组 DNA 构建物的构建，该 DNA 构建物包含编码本发明细胞色素 P450 单加氧酶的全部或部分多核苷酸，呈有义或反义取向，其中重组 DNA 构建物的表达导致在转化的宿主细胞中产生改变水平的 1-辛烯-3-醇。
• US4085127A
  申请人：——

  公开号：US4085127A

  公开（公告）日：1978-04-18