(8Z,11Z,14Z)-8,11,14-十七(碳)三烯醛 | 56797-44-5

• 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: (8Z,11Z,14Z)-8,11,14-十七(碳)三烯醛
• 英文名称: (8Z,11Z,14Z)-8,11,14-heptadecatrienal
• 英文别名: (8Z,11Z,14Z)-heptadecatrienal；heptadeca-8c,11c,14c-trienal；norlinolenaldehyde；norlinolenic aldehyde；(8Z,11Z,14Z)-heptadeca-8,11,14-trienal
• CAS: 56797-44-5
• 化学式: C₁₇H₂₈O
• 分子量: 248.409
• InChiKey: NIPNNUONNZABRE-PDBXOOCHSA-N

物化性质

• 沸点：
  352.7±21.0 °C(Predicted)
• 密度：
  0.864±0.06 g/cm3(Predicted)
• LogP：
  6.100 (est)
• 保留指数：
  1874;1852;1864
• 稳定性/保质期：

  存在于烟叶中。

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

制备方法与用途

合成制备方法

1. 烟草：18。

反应信息

• 作为反应物：
  描述：

  (8Z,11Z,14Z)-8,11,14-十七(碳)三烯醛 、 甲基锂 在 N-甲基吲哚酮 、 四丙基高钌酸铵 作用下， 生成 (9Z,12Z,15Z)-octadeca-9,12,15-trien-2-one
  参考文献：
  名称：

  Abnormal Catabolites of Unsaturated Fatty Acids by In Vitro Reaction of Crude Enzyme from Infected Higher Plants

  摘要：

  α-亚麻酸与从受感染南瓜中提取的粗酶（脂氧合酶）反应后，除 13S-hydroperoxy linolenic acid 外，还形成了 8Z、11Z、14Z-十七碳三烯醛（noraldehyde）及其酸（noracid）。由于从其他受感染植物的粗酶反应中也分离出了去甲醛及其酸，因此它们的形成似乎与高等植物的病原体感染有关。

  DOI：

  10.1246/cl.1994.761
• 作为产物：
  描述：

  Γ-十八碳三烯酸 在 2,4-dinitrophenylhydrazone 、 LCA(long chain aldehydes)-forming activity in Ulva pertusa fronds solubilized by Triton X-100 作用下， 反应 0.25h， 生成 (8Z,11Z,14Z)-8,11,14-十七(碳)三烯醛
  参考文献：
  名称：

  在绿藻 Ulva pertusa 中产生长链醛的酶系统的特异性

  摘要：

  摘要 在 4000 g 的匀浆沉淀物中发现了大部分酶活性产生长链醛 (LCA)，如 (8Z)-十七烯醛、(8Z,11Z)-十七碳烯醛、(8Z,11Z,14Z)-十七碳三烯醛。绿藻，Ulva pertusa。通过添加 0.2% Triton X-100，很容易从沉淀物中溶解 LCA 形成活性。溶解的 LCA 形成活性显示出最佳 pH 值范围为 8.5-9.5。α-亚麻酸是一种非常好的底物，但γ-亚麻酸是一种较差的活性底物。亚油酸是整个系列 (ω6Z,ω9Z)-二烯酸的最佳底物，其中链长从 C13 到 C20。

  DOI：

  10.1016/0031-9422(89)80021-4

文献信息

• Concise Synthesis of (8<i>Z</i>,11<i>Z</i>,14<i>Z</i>)-8,11,14-Heptadecatrienal, (7<i>Z</i>,10<i>Z</i>,13<i>Z</i>)-7,10,13-Hexadecatrienal, and (8<i>Z</i>,11<i>Z</i>)-8,11-Heptadecadienal, Components of the Essential Oil of Marine Green Alga<i>Ulva pertusa</i>
  作者：Yoshihiko AKAKABE、Kensuke WASHIZU、Kenji MATSUI、Tadahiko KAJIWARA

  DOI：10.1271/bbb.69.1348

  日期：2005.1

  The long-chain aldehydes, (8Z,11Z,14Z)-8,11,14-heptadecatrienal, (7Z,10Z,13Z)-7,10,13-hexadecatrienal, and (8Z,11Z)-8,11-heptadecadienal, were concisely synthesized by using Grignard coupling, catalytic hydrogenation with the Lindlar catalyst, and oxidation with Dess–Martin periodinane as the key steps. Particularly, (8Z,11Z,14Z)-8,11,14-heptadecatrienal and (7Z,10Z,13Z)-7,10,13-hexadecatrienal both possessed a seaweed-like odor.

  通过使用格氏偶联、Lindlar催化剂催化氢化和Dess–Martin高碘酸钠氧化作为关键步骤，简明地合成了长链醛类化合物，包括(8Z,11Z,14Z)-8,11,14-十七碳三烯醛、(7Z,10Z,13Z)-7,10,13-十六碳三烯醛和(8Z,11Z)-8,11-十七碳二烯醛。特别是，(8Z,11Z,14Z)-8,11,14-十七碳三烯醛和(7Z,10Z,13Z)-7,10,13-十六碳三烯醛都具有海藻般的气味。
• Enzymatic formation of unsaturated long chain fatty aldehydes in Ulva pertusa
  作者：Tadahiko Kajiwara、Hiroshi Yoshikawa、Takahiro Saruwatari、Akikazu Hatanaka、Tetsuo Kawai、Masakazu Ishihara、Tomoyuki Tsuneya

  DOI：10.1016/0031-9422(88)80419-9

  日期：1988.1

  Abstract (Z)-8-Heptadecenal, (Z,Z)-8, 11-heptadecadienal and 8,11,14-heptadecatrienal, were produced enzymatically from oleic, linoleic and linoleni

  摘要 (Z)-8-十七烯醛、(Z,Z)-8、11-十七碳二烯醛和 8,11,14-十七碳三烯醛是由油酸、亚油酸和亚麻油经酶促产生的
• α-Oxidation of Fatty Acids in Higher Plants
  作者：Mats Hamberg、Ana Sanz、Carmen Castresana

  DOI：10.1074/jbc.274.35.24503

  日期：1999.8

  A pathogen-inducible oxygenase in tobacco leaves and a homologous enzyme from Arabidopsis were recently characterized (Sanz, A., Moreno, J. I., and Castresana, C. (1998) Plant Cell 10, 1523-1537), Linolenic acid incubated at 23 degrees C with preparations containing the recombinant enzymes underwent alpha-oxidation with the formation of a chain-shortened aldehyde, i.e., 8(Z),11(Z),14(Z)-heptadecatrienal (83%), an alpha-hydroxy acid, 2(R)-hydroxy-9(Z),12(Z),15(Z)-octadecatrienoic acid (15%), and a chain-shortened fatty acid, 8(Z),11(Z),14(Z)-heptadecatrienoic acid (2%). When incubations were performed at 0 degrees C, 2(R)-hydroperoxy-9(Z),12(Z),15(Z)-octadecatrienoic acid was obtained as the main product. An intermediary role of 2(R)-hydroperoxy-9(Z),12(2),15(2)octadecatrienoic acid in alpha-oxidation was demonstrated by re-incubation experiments, in which the hydroperoxide was converted into the same alpha-oxidation products as those formed from linolenic acid. 2(R)-Hydroperoxy-9(Z),12(Z),15(Z)-octadecatrienoic acid was chemically unstable and had a half-life time in buffer of about 30 min at 23 degrees C, Extracts of cells expressing the recombinant oxygenases accelerated breakdown of the hydroperoxide (half-life time, about 3 min at 23 degrees C), however, this was not attributable to the recombinant enzymes since the same rate of hydroperoxide degradation was observed in the presence of control cells not expressing the enzymes. No significant discrimination between enantiomers was observed in the degradation of 2(R,S)-hydroperoxy-9(Z)-octadecenoic acid in the presence of recombinant oxygenases, A previously studied system for alpha-oxidation in cucumber was re-examined using the newly developed techniques and was found to catalyze the same conversions as those observed with the recombinant enzymes, i.e. enzymatic alpha-dioxygenation of fatty acids into 2(R)-hydroperoxides and a first order, non-stereoselective degradation of hydroperoxides into alpha-oxidation products. It was concluded that the recombinant enzymes from tobacco and Arabidopsis were both alpha-dioxygenases, and that members of this new class of enzymes catalyze the first step of alpha-oxidation in plant tissue.
• Fatty acid α-dioxygenases
  作者：Mats Hamberg、Inés Ponce de León、Ana Sanz、Carmen Castresana

  DOI：10.1016/s0090-6980(02)00040-0

  日期：2002.8

  This paper will briefly review the biochemistry, molecular biology and functionality of alpha-dioxygenases from tobacco, Arabidopsis, cucumber, pea, rice and algae. alpha-Dioxygenase treated in this review has emerged as a third group of fatty acid dioxygenases along with lipoxygenases and endoperoxide synthases. (C) 2002 Elsevier Science Inc. All rights reserved.