10-ODA | 79868-90-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 10-ODA
• 英文别名: 10-Oxodec-8-enoic acid
• CAS: 79868-90-9
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: YUAQBOMIASXPQW-UHFFFAOYSA-N

物化性质

• 沸点：
  348.5±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

• 作为产物：
  描述：

  10-氢过氧十八碳-8,12-二烯酸 在 PpoA from Aspergillus nidulans 作用下， 反应 0.67h， 生成 10-ODA 、 12,13-epoxy-10-hydroxyoctadec-8-enoic acid
  参考文献：
  名称：

  PpoC from Aspergillus nidulans is a fusion protein with only one active haem

  摘要：

  在裸曲霉（Aspergillus nidulans）中，Ppos[psi（早熟性诱导剂）产生氧合酶]是产生所谓的psi因子所必需的，这些因子是控制真菌有性和无性生命周期平衡的化合物。A. nidulans 的基因组中含有三种不同的 ppo 基因：ppoA、ppoB 和 ppoC。这三种酶都有两个不同的含血红素结构域：N 端区域的脂肪酸血红素过氧化物酶/二氧 化酶结构域和 C 端区域的 P450 血红素硫酸盐结构域。研究表明，PpoA 利用这两个血红素结构域进行双功能催化活性（亚油酸 8-二氧 化和 8-过氧化氢异构化），而我们发现 PpoC 显然只含有一个功能性血红素过氧化物酶/二氧 化酶结构域。因此，我们观察到 PpoC 主要催化亚油酸（18:2Δ9Z,12Z）的二氧化反应，生成 10-HPODE（10-氢过氧化十八碳二烯酸）。未检测到异构酶活性。此外，10-HPODE 还以较低的速率转化为 10-KODE（10-酮基十八碳二烯酸）和 10-HODE（10-羟基十八碳二烯酸）。与此同时，10-HPODE 会分解成 10-ODA（10-十八碳烯酸）和挥发性 C-8 醇，这些物质是蘑菇特有风味的主要成分。除了这些原理上的差异，我们还发现 PpoA 和 PpoC 可以将 8-HPODE 和 10-HPODE 转化为相应的环氧醇：12,13-环氧-8-HOME（其中 HOME 是羟基十八碳烯酸）和 12,13- 环氧-10-HOME。通过使用定点诱变，我们证明这两种酶在氧化 18:2Δ9Z,12Z 时具有相似的机制；它们都使用一个保守的酪氨酸残基进行催化，C-8 和 C-10 的定向氧合很可能是由二氧化酶结构域中保守的缬氨酸/亮氨酸残基控制的。

  DOI：

  10.1042/bj20091096

文献信息

• Substituted bicyclo (2,2,1)heptanes and bicyclo (2,2,1) hept-2-enes and their pharmaceutical compositions
  申请人：NATIONAL RESEARCH DEVELOPMENT CORPORATION

  公开号：EP0013607A1

  公开（公告）日：1980-07-23

  Novel bicyclo [2,2,1] heptanes and hept-2Z-enes are substituted at the 5-position by a 6-carboxyhex-2-enyl group or a modification thereof, and at the 6-position by an aldoxime or ketoxime group which is O-substituted by an aliphatic hydrocarbon residue, an aromatic residue, or an aliphatic hydrocarbon residue substituted directly orthrough an oxygen or sulphur atom by an aromatic residue. Such compounds may be prepared by the action of an oximating agent on an intermediate which is substituted at the 6-position by an aldehydic or ketonic carbonyl group. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.

  新型双环[2,2,1]庚烷和庚-2Z-烯在 5 位被 6-羧基己-2-烯基或其改性物取代，在 6 位被醛肟基或酮肟基取代，该醛肟基或酮肟基被脂肪烃残基、芳香族残基或直接通过氧原子或硫原子被芳香族残基取代的脂肪烃残基 O 取代。此类化合物可通过氧化剂对中间体的作用制备，中间体的 6 位被醛基或酮基羰基取代。这些化合物具有药物组合物的使用价值，特别是在抑制血栓素活性方面。
• Prostaglandins
  申请人：NATIONAL RESEARCH DEVELOPMENT CORPORATION

  公开号：EP0043292A2

  公开（公告）日：1982-01-06

  Novel compounds have a formula (I) wherein represents a bicyclo (2,2,1) hept-2Z-ene, bicyclo (2,2,1) heptane, 7-oxabicyclo (2,2,1) hept-2Z-ene, 7-oxabicyclo (2,2,1) heptane, bicyclo (2,2,2) oct-2Z-ene or bicyclo (2,2,2) octane substituted at the 5-position by the group R1 and at the 6-position by the group C(R2)=NR, a 6,6-dimethyl-bicyclo (3,1,1) heptane substituted at the 5- position by the group R' and at the 6-position by the group C(R2)=NR or at the 5-position by the group C(R2)=NR and at the 6-position by the group R1, a cyclohex-1-ene or cyclohexane substituted at the 4-position by the group R1 and at the 5-position by the group C(R2)=NR, or a 1-hydroxycyclopentane substituted at the 2-position by the group R1 and at the 2-position by the group C(R2)=NR, R1 is a 6-carboxyhex-2-enyl group or a modification thereof as defined herein, R2 is hydrogen, an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, and R is a group -OR3, -OR4, -A-R3 or -N=R5 in which A is -NH-, -NH.CO-, -NH.CO.CH2N(R6)-, -NH.SO2-, -NH.CO.NH or -NH.CS.NH- and wherein R3 is an aliphatic hydrocarbon group, an aromatic group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, R4 is an aliphatic hydrocarbon group which is substituted through an oxygen atom by an aliphatic hydrocarbon group which is itself substituted by an aromatic group, R5 is an aliphatic hydrocarbon group, an aromatic group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, and R6 is hydrogen, an aliphatic hydrocarbon group, an aromatic group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, with the proviso that when R is a group -OR3, -NH.COR3 or-NH.CO.NHR3 then excludes bicyclo (2,2,1) hept-2Z-enes and bicyclo (2,2,1) heptanes. The compounds are of value for use in phar. maceutical compositions particularly in the context of the inhibition of thromboxane activity.

  新型化合物具有式 (I) 其中 代表在 5 位被基团 R1 取代、在 6 位被基团 C(R2)=NR 取代的双环(2,2,1)庚-2Z-烯、双环(2,2,1)庚烷、7-氧杂双环(2,2,1)庚烷、双环(2,2,2)辛-2Z-烯或双环(2,2,2)辛烷、在 5 位被基团 R'取代、在 6 位被基团 C(R2)=NR 取代的 6,6-二甲基双环(3,1,1)庚烷，或在 5 位被基团 C(R2)=NR 取代、在 6 位被基团 R1 取代的 6,6-二甲基双环(3,1,1)庚烷、在 4 位被基团 R1 取代且在 5 位被基团 C(R2)=NR 取代的环己-1-烯或环己烷，或在 2 位被基团 R1 取代且在 2 位被基团 C(R2)=NR 取代的 1-羟基环戊烷、R1 是本文定义的 6-羧基己-2-烯基或其改性物，R2 是氢、脂肪族烃基或直接或通过氧原子或硫原子被芳香族基取代的脂肪族烃基，R 是基团-OR3、-OR4、-A-R3 或-N=R5，其中 A 是-NH-、-NH.CO-、-NH.CO.CH2N(R6)-、-NH.SO2-、-NH.CO.NH 或 -NH.CS.其中 R3 是直接或通过氧原子或硫原子被芳香基团取代的脂肪烃基团、芳香基团或脂肪烃基团，R4 是通过氧原子被本身被芳香基团取代的脂肪烃基团，R5 是脂肪烃基团、R6是氢、脂肪族烃基、芳香族基团或直接或通过氧原子或硫原子被芳香族基团取代的脂肪族烃基，但当R是-OR3、-NH.COR3或-NH.CO.NHR3，则 不包括双环(2,2,1)庚-2Z-烯和双环(2,2,1)庚烷。这些化合物在医药组合物中具有使用价值，特别是在抑制血栓素活性方面。
• Prostaglandin intermediates
  申请人：NATIONAL RESEARCH DEVELOPMENT CORPORATION

  公开号：EP0111955A1

  公开（公告）日：1984-06-27

  Novel compounds have a formula (I) wherein represents a bicyclo [2,2,1] hept-2Z-ene, bicyclo [2,2,1] heptane, 7-oxabicyclo [2,2,1] hept-2Z-ene, 7-oxabicyclo [2,2,1] heptane, bicyclo [2,2,2] oct-2Z-ene or bicyclo [2,2,2] octane substituted at the 5-position by the group R' and at the 6-position by the group C(R2)=NR, a 6,6-dimethyl-bicyclo [3,1,1] heptane substituted at the 5-position by the group R' and at the 6-position by the group C(R2)=NR or at the 5-position by the group C(R2)=NR and at the 6-position by the group R', a cyclohex-1-ene or cyclohexane substituted at the 4-position by the group R1 and at the 5-position by the group C(R2)=NR, or a 1-hydroxycyclopentane substituted at the 2-position by the group R1 and at the 2-position by the group C(R2)=NR, R1 is a 6-carboxyhex-2-enyl group or a modification thereof as defined herein, R2 is hydrogen, an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, and R is a group -OR3, -OR4, -A-R3 or -N=R5 in which A is -NH-, -CH.CO-, -NH.CO.CH2N(R6)-, -NH.S02-, -NH.CO.NH or -NH.CS.NH-and wherein R3 is an aliphatic hydrocarbon group, an aromatic group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, R4 is an aliphatic hydrocarbon group which is substituted through an oxygen atom by an aliphatic hydrocarbon group which is itself substituted by an aromatic group, R5 is an aliphatic hydrocarbon group, an aromatic group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, and R6 is hydrogen, an aliphatic hydrocarbon group, an aromatic group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, with the proviso that when R is a group -OR3, - NH.COR3 or -NH.CO.NHR3 then excludes bicyclo [2,2,1] hept-2Z-enes and bicyclo [2,2,1] heptanes. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.

  新型化合物具有式 (I) 其中 代表在 5 位被基团 R'取代、在 6 位被基团 C(R2)=NR.取代的双环[2,2,1]庚-2Z-烯、双环[2,2,1]庚烷、7-氧杂双环[2,2,1]庚烷、双环[2,2,2]辛-2Z-烯或双环[2,2,2]辛烷、在 5 位被基团 R'取代、在 6 位被基团 C(R2)=NR 取代的 6,6-二甲基双环[3,1,1]庚烷，或在 5 位被基团 C(R2)=NR 取代、在 6 位被基团 R'取代的 6,6-二甲基双环[3,1,1]庚烷、在 4 位被基团 R1 取代、在 5 位被基团 C(R2)=NR 取代的环己-1-烯或环己烷，或在 2 位被基团 R1 取代、在 2 位被基团 C(R2)=NR 取代的 1-羟基环戊烷、R1 是本文定义的 6-羧基己-2-烯基或其改性物，R2 是氢、脂肪族烃基或直接或通过氧原子或硫原子被芳香族基取代的脂肪族烃基，R 是基团-OR3、-OR4、-A-R3 或-N=R5，其中 A 是-NH-、-CH.CO-、-NH.CO.CH2N(R6)-、-NH.S02-、-NH.CO.NH 或 -NH.CS.其中 R3 是脂肪族烃基、芳香族基团或直接或通过氧原子或硫原子被芳香族基团取代的脂肪族烃基；R4 是通过氧原子被脂肪族烃基取代的脂肪族烃基，该脂肪族烃基本身被芳香族基团取代；R5 是脂肪族烃基、R6是氢、脂肪族烃基、芳香族基团或直接或通过氧原子或硫原子被芳香族基团取代的脂肪族烃基，但当R是-OR3、-NH.COR3或-NH.CO.NHR3，则 不包括双环[2,2,1]庚-2Z-烯和双环[2,2,1]庚烷。这些化合物具有药物组合物的使用价值，特别是在抑制血栓素活性方面。
• 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。
• Method of producing fungal materials and objects made therefrom
  申请人：Mycoworks, Inc.

  公开号：US10687482B2

  公开（公告）日：2020-06-23

  A method of forming fungal materials and fungal objects from those fungal materials, the method comprising the steps of growing a first fungal tissue in contact with a nutritive vehicle; supplying a porous material in contact with said first fungal tissue; directing growth of said fungal tissue through said porous material such that a portion of said fungal tissue comprises a first fungal material having first fungal hyphae; optionally incorporating composite material; directing a change in the composition or growth pattern of at least some of said first fungal hyphae; separating at least a portion of the first fungal material from said nutritive vehicle; obtaining a second fungal material having second fungal hyphae; and forming a fungal object by encouraging fused growth between said first fungal material and said second fungal material and optionally incorporating composite material.

  一种用真菌材料和真菌物体形成真菌材料和真菌物体的方法，该方法包括以下步骤 生长与营养载体接触的第一真菌组织；提供与所述第一真菌组织接触的多孔材料；引导所述真菌组织通过所述多孔材料生长，使所述真菌组织的一部分包括具有第一真菌菌丝的第一真菌材料；选择性地加入复合材料；引导至少部分所述第一真菌菌丝的组成或生长模式发生变化；将至少部分第一真菌材料从所述营养载体中分离出来；获得具有第二真菌菌丝的第二真菌材料；以及通过促进所述第一真菌材料和所述第二真菌材料之间的融合生长并选择性地加入复合材料，形成真菌物体。