6,10-二甲基-3,5,9-十一碳三烯-2-酮 | 38237-36-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6,10-二甲基-3,5,9-十一碳三烯-2-酮
• 英文名称: (E)-6,10-dimethylundeca-5,10-dien-2-one
• 英文别名: (5E)-6,10-dimethylundeca-5,10-dien-2-one
• CAS: 38237-36-4
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: ZDZHCIAFSISUHF-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914190090

反应信息

• 作为反应物：
  描述：

  氰甲基磷酸二乙酯 、 6,10-二甲基-3,5,9-十一碳三烯-2-酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 生成 (2Z,6E)-3,7,11-trimethyldodeca-2,6,11-trienenitrile 、 (2E,6E)-3,7,11-trimethyldodeca-2,6,11-trienenitrile
  参考文献：
  名称：

  通过自由基环化控制制备高度官能化萜烯环戊烷的区域选择性和非对映选择性

  摘要：

  适当官能化的无环 C10 环氧-聚戊二烯的二茂钛介导的环化以中等立体选择性导致具有三个连续立体中心的官能化萜烯环戊烷的高产率。这些高度官能化的环戊烷是合成几种天然化合物的有用中间体，这些天然化合物的结构中包含这种有趣的亚基。生成环戊烷的过程的区域选择性和环化的立体选择性都可以通过使用丙二酰衍生物或 α,β-不饱和腈作为自由基受体来控制。

  DOI：

  10.1002/ejoc.201100400
• 作为产物：
  描述：

  (5E)-9-chloro-6,10-dimethylundeca-5,10-dien-2-one 在 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以80%的产率得到6,10-二甲基-3,5,9-十一碳三烯-2-酮
  参考文献：
  名称：

  通过自由基环化控制制备高度官能化萜烯环戊烷的区域选择性和非对映选择性

  摘要：

  适当官能化的无环 C10 环氧-聚戊二烯的二茂钛介导的环化以中等立体选择性导致具有三个连续立体中心的官能化萜烯环戊烷的高产率。这些高度官能化的环戊烷是合成几种天然化合物的有用中间体，这些天然化合物的结构中包含这种有趣的亚基。生成环戊烷的过程的区域选择性和环化的立体选择性都可以通过使用丙二酰衍生物或 α,β-不饱和腈作为自由基受体来控制。

  DOI：

  10.1002/ejoc.201100400

文献信息

• Process for preparing compositions containing unsaturated lactones, products produced thereby and organoleptic uses of said products
  申请人：INTERNATIONAL FLAVORS & FRAGRANCES INC.

  公开号：EP0354000A2

  公开（公告）日：1990-02-07

  Described is a process for the preparation of compositions of matter containing unsaturated lactones defined according to the generic structure: wherein R represents C6 alkyl or alkenyl; and X represents C2, C4 or C6 alkylene or alkenylene; with the provisos that R is C6 alkyl when X is alkenylene and R is C6 alkenyl when X is alkylene by means of the sequential steps of (i) fermentation of castor oil or ricinoleic acid using a microorganism selected from the group consisting of: Candida petrophilum, ATCC 20226; Candida oleophila, ATCC 20177; Candida sp., ATCC 20504; and Candida sake, ATCC 28137 whereby gamma hydroxydecanoic acid and a mixture of other acids defined according to the generic structure: is formed wherein Y represents an oxo-saturated, oxo-unsaturated or di-unsaturated C9, C11 or C13 moiety according to the reaction: (ii) lactonization of the resulting gamma hydroxydecanoic acid by means of simultaneous acidification and heating according to the reaction: and (iii) lactonization (via distillation) of one or more of the resulting acids defined according to the structure: to form one or more lactones defined according to the generic structure: according to the reaction: wherein the sum of the number of carbon atoms in the X moiety and in the R moiety is equal to the number of carbon atoms in the Y moiety minus 1. Also described are the products produced according to such process as well as their organoleptic utilities for augmenting or enhancing the aroma or taste of consumable materials selected from the group consisting of perfume compositions, colognes, perfumed articles, perfumed polymers, foodstuffs, chewing gums, medicinal products, toothpastes, chewing tobaccos and smoking tobaccos.

  本发明描述了一种制备含有根据通用结构定义的不饱和内酯的物质组合物的工艺： 其中R代表C6烷基或烯基；X代表C2、C4或C6亚烷基或烯基；但条件是当X为烯基时，R为C6烷基；当X为亚烷基时，R为C6烯基，制备方法为(i)使用选自以下组成的组的微生物发酵蓖麻油或蓖麻油酸，(ii)使用选自以下组成的组的微生物发酵蓖麻油或蓖麻油酸，(iii)使用选自以下组成的组的微生物发酵蓖麻油或蓖麻油酸：Candida petrophilum，ATCC 20226；Candida oleophila，ATCC 20177；Candida sp.，ATCC 20504；和 Candida sake，ATCC 28137： 其中 Y 代表氧饱和、氧不饱和或二不饱和 C9、C11 或 C13 分子： (ii) 根据反应，通过同时酸化和加热，对生成的γ-羟基癸酸进行内酯化： 和 (iii) （通过蒸馏）对所得到的一种或多种根据结构定义的酸进行内酯化： 形成一种或多种按通用结构定义的内酯： 根据反应 其中 X 分子和 R 分子的碳原子数之和等于 Y 分子的碳原子数减去 1。 此外，还描述了根据这种工艺生产的产品及其感官效用，这些产品用于增加或提高从香水组合物、古龙水、香水制品、香味聚合物、食品、口香糖、医药产品、牙膏、咀嚼烟草和吸烟烟草组成的组中选出的消耗材料的香气或味道。
• Octalactone-containing composition, fermentation process for producing same and organoleptic uses thereof
  申请人：INTERNATIONAL FLAVORS & FRAGRANCES INC.

  公开号：EP0519481A2

  公开（公告）日：1992-12-23

  The present invention is directed to a microbiological process for the production of compositions containing a major proportion of gamma octalactone generically defined according to the structure: containing the stereoisomers having the structures:

  本发明涉及一种微生物工艺，用于生产含有按结构通称的γ-辛内酯主要比例的组合物： 含有具有以下结构的立体异构体：
• 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。