十四碳-7-烯酸 | 2430-95-7

• 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: 十四碳-7-烯酸
• 英文名称: (7Z)-tetradec-7-enic acid
• 英文别名: (Z)-tetradec-7-enoic acid；(Z)-7-Tetradecenoic acid；tetradec-7c-enoic acid；Tetradec-7c-ensaeure；Tetradecensaeure(cis-Δ⁷)；Tetradecen-(7c)-saeure-(1)；7Z-tetradecenoic acid
• CAS: 2430-95-7
• 化学式: C₁₄H₂₆O₂
• 分子量: 226.359
• InChiKey: ZVXDGKJSUPWREP-FPLPWBNLSA-N

物化性质

• 熔点：
  4.0-5.0 °C
• 沸点：
  344.7±21.0 °C(Predicted)
• 密度：
  0.913±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916190090

反应信息

• 作为反应物：
  描述：

  十四碳-7-烯酸 在 氯磺酰异氰酸酯 、 三氟化硼乙醚 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以91%的产率得到(Z )-tetradec-7-enenitrile
  参考文献：
  名称：

  长链烷基氰化物：假单胞菌和微单孢菌细菌释放的前所未有的挥发性化合物

  摘要：

  对细菌培养物中挥发物的分析表明，长链脂族腈是一种新型的天然产物。尽管结构不同，但此类革兰氏阳性菌既由革兰氏阳性单孢菌也由革兰氏阴性假单胞菌产生。脂肪酸生物合成中链伸长和脱水的可变序列会导致带有ω-7双键的直链饱和或不饱和腈，例如（Z）-11-十八烯腈或带有双键的甲基支链的不饱和腈在C-3处，例如（Z）-13-甲基十四烷基-3-烯腈。腈的生物合成从脂肪酸开始，然后将脂肪酸转化为酰胺，最后脱水。通过质谱，合成和氘标记前体的进料实验阐明了19种天然化合物的结构和生物合成。一些腈显示出抗微生物活性，例如，对多抗金黄色葡萄球菌菌株具有抗微生物活性。

  DOI：

  10.1002/anie.201611940
• 作为产物：
  描述：

  6-溴正己醇 在 甲醇 、 Jones reagent 、 正丁基锂 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 hexanes 、 二氯甲烷 、 乙酸乙酯 、 丙酮 为溶剂， 反应 29.58h， 生成 十四碳-7-烯酸
  参考文献：
  名称：

  Synthesis of highly enantioenriched hydroxy- and dihydroxy-fatty esters: substrate precursors for cytochrome P450BioI

  摘要：

  A series of highly enantioenriched hydroxy- and dihydroxy-fatty esters were required as part of our ongoing investigation into cytochrome P450(BioI). This mediates the biosynthesis of pimelic acid via C-C bond cleavage of long chain fatty acids within Bacillus subtilis. Herein we report the synthesis of various stereoisomers of methyl 7-hydroxytetradecanoate, methyl 8-hydroxytetradecanoate, and methyl 7,8-dihydroxytetradecanoate in highly enantioenriched form, using a combination of asymmetric synthesis and a preparative enantioselective HPLC is reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.027

文献信息

• Acyl-group specificity of AHL synthases involved in quorum-sensing in <i>Roseobacter</i> group bacteria
  作者：Lisa Ziesche、Jan Rinkel、Jeroen S Dickschat、Stefan Schulz

  DOI：10.3762/bjoc.14.112

  日期：——

  N-Acylhomoserine lactones (AHLs) are important bacterial messengers, mediating different bacterial traits by quorum sensing in a cell-density dependent manner. AHLs are also produced by many bacteria of the marine Roseobacter group, which constitutes a large group within the marine microbiome. Often, specific mixtures of AHLs differing in chain length and oxidation status are produced by bacteria, but how the biosynthetic enzymes, LuxI homologs, are selecting the correct acyl precursors is largely unknown. We have analyzed the AHL production in Dinoroseobacter shibae and three Phaeobacter inhibens strains, revealing strain-specific mixtures. Although large differences were present between the species, the fatty acid profiles, the pool for the acyl precursors for AHL biosynthesis, were very similar. To test the acyl-chain selectivity, the three enzymes LuxI₁ and LuxI₂ from D. shibae DFL-12 as well as PgaI₂ from P. inhibens DSM 17395 were heterologously expressed in E. coli and the enzymes isolated for in vitro incubation experiments. The enzymes readily accepted shortened acyl coenzyme A analogs, N-pantothenoylcysteamine thioesters of fatty acids (PCEs). Fifteen PCEs were synthesized, varying in chain length from C₄ to C₂₀, the degree of unsaturation and also including unusual acid esters, e.g., 2E,11Z-C18:2-PCE. The latter served as a precursor of the major AHL of D. shibae DFL-12 LuxI₁, 2E,11Z-C18:2-homoserine lactone (HSL). Incubation experiments revealed that PgaI₂ accepts all substrates except C₄ and C₂₀-PCE. Competition experiments demonstrated a preference of this enzyme for C₁₀ and C₁₂ PCEs. In contrast, the LuxI enzymes of D. shibae are more selective. While 2E,11Z-C18:2-PCE is preferentially accepted by LuxI₁, all other PCEs were not, except for the shorter, saturated C₁₀–C₁₄-PCEs. The AHL synthase LuxI₂ accepted only C₁₄ PCE and 3-hydroxydecanoyl-PCE. In summary, chain-length selectivity in AHLs can vary between different AHL enzymes. Both, a broad substrate acceptance and tuned specificity occur in the investigated enzymes.

  N-酰基脱氨核糖乳酸（AHLs）是重要的细菌信使，在细胞密度依赖的方式中介导不同的细菌特征。AHLs也被许多海洋玫瑰细菌组的细菌产生，这在海洋微生物组中占据着一个大的群体。通常，细菌会产生具有不同链长和氧化状态的AHLs的特定混合物，但是生物合成酶LuxI同源物如何选择正确的酰前体大部分是未知的。我们分析了Dinoroseobacter shibae和三株Phaeobacter inhibens菌株中的AHL产生，揭示了菌株特异性混合物。尽管这些物种之间存在很大差异，但脂肪酸谱，即AHL生物合成的酰前体池，非常相似。为了测试酰链选择性，从D. shibae DFL-12的三种酶LuxI1和LuxI2以及从P. inhibens DSM 17395的PgaI2在大肠杆菌中异源表达，并将酶分离用于体外孵育实验。这些酶容易接受缩短的酰辅酶A类似物，即脂肪酸的泛酸半胱氨基乙酰硫酯（PCEs）。合成了15种PCEs，链长从C4到C20不等，不饱和度不同，还包括不寻常的酸酯，例如2E,11Z-C18:2-PCE。后者作为D. shibae DFL-12 LuxI1的主要AHL的前体，2E,11Z-C18:2-脱氨核糖乳酸（HSL）。孵育实验表明，PgaI2接受除C4和C20-PCE之外的所有底物。竞争实验表明，这种酶对C10和C12 PCE有偏好。相比之下，D. shibae的LuxI酶更具选择性。虽然2E,11Z-C18:2-PCE优先被LuxI1接受，但除了较短的饱和C10-C14-PCE之外，所有其他PCE都不被接受。AHL合酶LuxI2仅接受C14 PCE和3-羟基癸酰-PCE。总之，AHL中的链长选择性在不同的AHL酶之间可能有所不同。在研究的酶中既有广泛的底物接受性，也有调节的特异性。
• Oxygenated <i>N</i>-Acyl Alanine Methyl Esters (NAMEs) from the Marine Bacterium <i>Roseovarius tolerans</i> EL-164
  作者：Hilke Bruns、Jennifer Herrmann、Rolf Müller、Hui Wang、Irene Wagner Döbler、Stefan Schulz

  DOI：10.1021/acs.jnatprod.7b00757

  日期：2018.1.26

  carrying a rare terminally oxidized acyl chain are reported here. The compounds (Z)-N-16-hydroxyhexadec-9-enoyl-l-alanine methyl ester (Z9-16-OH-C16:1-NAME, 3) and (Z)-N-15-carboxypentadec-9-enoyl-l-alanine methyl ester (16COOH-C16:1-NAME, 4) were isolated, and the structures were determined by NMR and MS experiments. Both compounds were synthesized to prove assignments and to test their biological activity

  除结缔组织相关的N-酰基高丝氨酸内酯（AHLs）（在红细菌科中广泛存在的细菌信号化合物）外，海洋细菌耐受性玫瑰红细菌EL-164（红杆菌科）还可以产生独特的N-酰基丙氨酸甲酯（NAMEs）。这里报道了两个罕见的带有稀有的末端氧化酰基链的NAMEs的结构。化合物（Z）-N -16-羟基十六烷基-9-烯酰基-1-丙氨酸甲酯（Z9-16-OH-C16：1-NAME，3）和（Z）-N -15-羧基戊烯-9-烯酰基-升-丙氨酸甲酯（16COOH-C16：1-NAME，4分离），并通过NMR和MS实验确定结构。合成了这两种化合物以证明其归属并测试其生物学活性。最后，合成了非天然的，结构上相关的Z9-3-OH-C16：1-NAME（18），以研究结构上相关的NAME的质谱。化合物3对诸如芽孢杆菌，链球菌，微球菌或Mucor菌株等微生物表现出中等的抗菌活性。与AHL相比，未观察到群体感应或群体猝灭活动。
• Synthesis of Carboxymethyl GLA-60 Ether Derivatives Containing an Olefin in Their Chains and Their LPS-Antagonistic Activities
  作者：Tsuyoshi Nakamura、Yukiko Watanabe、Masao Shiozaki、Saori Kanai、Shin-ichi Kurakata

  DOI：10.1246/bcsj.76.1011

  日期：2003.5

  Anomeric carboxymethyl GLA-60 olefine derivatives having ether chains instead of ester chains in their side chains were synthesized and their biological activities toward both human U937 cells and mouse PEC-macrophage cells were measured. The species-specific behavior of these compounds in humans (LPS-antagonistic) and mice (very weak LPS-antagonistic, but almost inactive) found this time was different from that in humans (LPS-antagonistic) and mice (endotoxic) found in the biosynthetic precursor of lipid A, such as lipid IVa. However, this fact also shows, interestingly enough, that a difference exists in the molecular recognition between human and mouse LPS receptors.

  合成了具有醚链而非酯链的异构体羧甲基GLA-60烯烃衍生物，并测定了它们对人类U937细胞和小鼠PEC-巨噬细胞的生物活性。这些化合物在人体（LPS拮抗作用）和小鼠（LPS拮抗作用非常弱，但几乎没有活性）中的物种特异性行为与脂质A的生物合成前体脂质IVa中发现的人类（LPS拮抗作用）和小鼠（内毒性）的行为不同。然而，这一事实有趣地表明，人类和小鼠LPS受体之间存在分子识别的差异。
• Substrate specificity of acetyltransferase and reductase enzyme systems used in pheromone biosynthesis by Asian corn borer,Ostrinia furnacalis
  作者：Cheng-Hua Zhao、Fang Lu、Marie Bengtsson、Christer Löfstedt

  DOI：10.1007/bf02035148

  日期：1995.10

  tested fatty alcohols indicated that the acetyltransferase has a low substrate specificity. Most of the corresponding tetradecenoic acids could also be converted to the respective acetates. However, very different conversion rates among the tested fatty acids demonstrated that the reductase system has a higher substrate specificity than the acetyltransferase. The conversion rates of mostE isomers were

  通过局部应用信息素腺体的前体，在体内研究了乙酰转移酶和还原酶系统在信息素生物合成中使用的 Ostrinia furnacalis (Lepidoptera: Pyralidae) 的底物特异性。每个十四烯醇，双键位置（从 7 到 13）和双键的几何形状不同，都被乙酰转移酶转化为相应的乙酸盐。所有测试的脂肪醇转化率的相似性表明乙酰转移酶具有低底物特异性。大多数相应的十四碳烯酸也可以转化为相应的乙酸酯。然而，测试的脂肪酸之间非常不同的转化率表明还原酶系统比乙酰转移酶具有更高的底物特异性。大多数 E 异构体的转化率高于相应的 Z 异构体的转化率，但 (Delta)-11-十四碳烯酸除外，其中更多的 Z 异构体转化为产物。饱和十四烷酸以高速率转化为相应的乙酸盐；较短的同系物十三烷酸的转化率较低 (56%)，而较长的同系物十五烷酸和十六烷酸各自的乙酸酯的转化率是微不足道的 (<5%)。本研究的结果表
• Highly efficient traps for the capture of insects
  申请人：Montedison S.p.A.

  公开号：EP0160712A1

  公开（公告）日：1985-11-13

  There are described traps for the capture of insects, of the type comprising a capturing chamber with a funnel-shaped closure, the efficiency of which is increased by a polytetrafluoroethylene coating of the inner walls of the funnel. Said traps, which may be baited either by pherohormone dispensers or by a phagoattracting agent, may be used both for the assessment of the insect population density in a determined area, and for the capture of insects in bulk.

  有一种用于捕捉昆虫的诱捕器，它包括一个带有漏斗状封闭装置的捕捉室，漏斗内壁的聚四氟乙烯涂层提高了捕捉效率。 这种诱捕器可以使用嗜血激素分配器或噬菌体引诱剂作为诱饵，既可用于评估某一确定区域的昆虫种群密度，也可用于捕捉大量昆虫。