(9Z,12Z)-9,12-十八碳二烯酸-9,10,12,13-D4 | 79050-23-0

• 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: (9Z,12Z)-9,12-十八碳二烯酸-9,10,12,13-D4
• 英文名称: [9,10,12,13-2H]-(Z,Z)-9,12-octadecadienoic acid
• 英文别名: <9,10,12,13-2H4>linoleic acid；[9,10,12,13-2H4]linoleic acid；Linoleic Acid-d4；(9Z,12Z)-9,10,12,13-tetradeuteriooctadeca-9,12-dienoic acid
• CAS: 79050-23-0
• 化学式: C₁₈H₃₂O₂
• 分子量: 284.419
• InChiKey: OYHQOLUKZRVURQ-GPTDOFLBSA-N

物化性质

• 溶解度：
  0.15 M Tris-HCl pH 8.5：>1 mg/ml（来自油酸）； DMF：>100 mg/ml（来自油酸）； DMSO：>100 mg/ml（来自油酸）；乙醇：>100 mg/ml（来自油酸）； PBS pH 7.2：<100 μg/ml（来自油酸）

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 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：

  (9Z,12Z)-9,12-十八碳二烯酸-9,10,12,13-D4 在 氧气 作用下， 反应 0.75h， 生成 <9,10,12,13-2H4>-(9S)-9-hydroperoxyoctadeca-10(E),12(Z)-dienoic acid
  参考文献：
  名称：

  An isotopic study (2H and 18O) of the enzymic conversion of linoleic acid into colneleic acid with carbon chain fracture: the origin of shorter chain aldehydes

  摘要：

  Contrary to earlier reports, the divinyl 9-ether oxygen of coloneleic acid is shown by experiment with O-18(2) to originate from oxygen, not water. Using [9,10,12,13-H-2(4)]-9(S)-hydroperoxyoctadeca-10(E), 12(Z)-dienoic acid, made enzymically from synthetic [9,10,12,13-H-2(4)]linoleic acid, it is found that the distribution of deuterium as determined by NMR and mass spectrometry in the fractured carbon chain of colneleic acid formed by potato enzyme, is consistent with the intervention of an epoxycarbonium ion intermediate. Though divinyl acids such as colneleic and colnelenic acid give the expected shorter chain aldehydes on treatment with aqueous acid, it is likely that the latter are formed in most plants by trapping of a monovinyl oxonium ion rather than by rehydration of colneleic and colnelenic acid.

  DOI：

  10.1039/p19910000567
• 作为产物：
  描述：

  1-溴-2辛炔 在 氢氧化钾 、 硼氘化钠 、 2-甲基-2-丁烯 、 三氟化硼乙醚 、 乙基溴化镁 作用下， 以 乙醚 、 乙醇 、 二乙二醇二甲醚 、 水 为溶剂， 反应 29.0h， 生成 (9Z,12Z)-9,12-十八碳二烯酸-9,10,12,13-D4
  参考文献：
  名称：

  An isotopic study (2H and 18O) of the enzymic conversion of linoleic acid into colneleic acid with carbon chain fracture: the origin of shorter chain aldehydes

  摘要：

  Contrary to earlier reports, the divinyl 9-ether oxygen of coloneleic acid is shown by experiment with O-18(2) to originate from oxygen, not water. Using [9,10,12,13-H-2(4)]-9(S)-hydroperoxyoctadeca-10(E), 12(Z)-dienoic acid, made enzymically from synthetic [9,10,12,13-H-2(4)]linoleic acid, it is found that the distribution of deuterium as determined by NMR and mass spectrometry in the fractured carbon chain of colneleic acid formed by potato enzyme, is consistent with the intervention of an epoxycarbonium ion intermediate. Though divinyl acids such as colneleic and colnelenic acid give the expected shorter chain aldehydes on treatment with aqueous acid, it is likely that the latter are formed in most plants by trapping of a monovinyl oxonium ion rather than by rehydration of colneleic and colnelenic acid.

  DOI：

  10.1039/p19910000567

文献信息

• Synthesis of linoleic acids combinatorially labeled at the vinylic positions as substrates for lipoxygenases
  作者：Matthew P. Meyer、Judith P. Klinman

  DOI：10.1016/j.tetlet.2008.04.023

  日期：2008.5

  inflammation-related human diseases. Soybean lipoxygenase-1 is the archetypical example of known lipoxygenases. Here we report the synthesis of linoleic acid and (11,11)-d2-linoleic acid which are combinatorially labeled at the vinylic positions (9, 10, 12, and 13). Combinatorial labeling schemes allow for the simultaneous determination of KIEs in enzymatic reactions using NMR. Substrates are, thus, available

  哺乳动物脂氧合酶与多种炎症相关的人类疾病有关。大豆脂氧合酶-1 是已知脂氧合酶的典型例子。在这里，我们报告了亚油酸和 (11,11)-d2-亚油酸的合成，它们在乙烯基位置（9、10、12 和 13）进行了组合标记。组合标记方案允许使用 NMR 同时测定酶促反应中的 KIE。因此，底物可用作脂氧合酶动力学同位素效应 (KIE) 研究中详细机制的探针。
• The conversion of linoleic acid (13S)-hydroperoxide into (13R)-hydroxy-12-oxo-octadec-(9Z)-enoic acid and 9-hydroxy-12-oxo-octadec-(10E)-enoic acid by a flax enzyme. Isotopic evidence for allene epoxide intermediates
  作者：Leslie Crombie、David O. Morgan

  DOI：10.1039/c39880000556

  日期：——

  Conversion of [9,10,12,13-2H4]linoleic acid, via its 13-hydroperoxide, into the γ-ketol (9) by a flax enzyme, with loss of C-13-[2H], can only satisfactorily be explained by the intervention of an allene epoxide intermediate; α-ketol (2) formation involves a similar mechanism.

  [9,10,12,13-的转换2 ħ 4 ]亚油酸，通过其13-氢过氧化物，进入γ-酮醇（9）由亚麻酶，具有C-13- [损耗2 H]，罐仅能通过烯丙基环氧中间体的干预来令人满意地解释；α-酮醇（2）的形成涉及类似的机理。
• Crombie, Leslie; Morgan, David O., Journal of the Chemical Society. Perkin transactions I, 1991, # 3, p. 577 - 580
  作者：Crombie, Leslie、Morgan, David O.

  DOI：——

  日期：——
• CROMBIE, LESLIE;MORGAN, DAVID O., J. CHEM. SOC. CHEM. COMMUN.,(1988) N 8, 556-557
  作者：CROMBIE, LESLIE、MORGAN, DAVID O.

  DOI：——

  日期：——
• An isotopic study (2H and 18O) of the enzymic conversion of linoleic acid into colneleic acid with carbon chain fracture: the origin of shorter chain aldehydes
  作者：Leslie Crombie、David O. Morgan、Elisabeth H. Smith

  DOI：10.1039/p19910000567

  日期：——

  Contrary to earlier reports, the divinyl 9-ether oxygen of coloneleic acid is shown by experiment with O-18(2) to originate from oxygen, not water. Using [9,10,12,13-H-2(4)]-9(S)-hydroperoxyoctadeca-10(E), 12(Z)-dienoic acid, made enzymically from synthetic [9,10,12,13-H-2(4)]linoleic acid, it is found that the distribution of deuterium as determined by NMR and mass spectrometry in the fractured carbon chain of colneleic acid formed by potato enzyme, is consistent with the intervention of an epoxycarbonium ion intermediate. Though divinyl acids such as colneleic and colnelenic acid give the expected shorter chain aldehydes on treatment with aqueous acid, it is likely that the latter are formed in most plants by trapping of a monovinyl oxonium ion rather than by rehydration of colneleic and colnelenic acid.