(E)-癸-2-烯二酸 | 37443-67-7

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: (E)-癸-2-烯二酸
• 中文别名: 反-2-癸烯二酸
• 英文名称: 2E-decene-1,10-dioic acid
• 英文别名: trans-2-decenedioic acid；(E)-2-decenadioic acid；(E)-2-decenedioic acid；(2E)-decenedioic acid；dec-2E-enedioic acid；dec-2t-enedioic acid；2E-Decenedioic acid；(E)-dec-2-enedioic acid
• CAS: 37443-67-7
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: XUNMWLWTZWWEIE-FNORWQNLSA-N

物化性质

• 沸点：
  409.4±38.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 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：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存于室温下，密封保存，并确保环境干燥。

反应信息

• 作为产物：
  描述：

  7-Formyl-4Z-heptenoic acid 在 palladium on activated charcoal 哌啶 、 氢气 作用下， 以 溶剂黄146 为溶剂， 20.0~115.0 ℃ 、2.03 MPa 条件下， 反应 47.0h， 生成 (E)-癸-2-烯二酸
  参考文献：
  名称：

  A new route for the synthesis of 10-hydroxydec-2E-enoic and dec-2E-enedioic acids

  摘要：

  DOI：

  10.1007/bf00575161

文献信息

• A NOVEL SYNTHESIS OF ROYAL JELLY ACIDS AND QUEEN SUBSTANCE BY THE FIVE CARBON HOMOLOGATION USING β-VINYL-β-PROPIOLACTONE
  作者：Tamotsu Fujisawa、Toshio Sato、Toshiyuki Itoh

  DOI：10.1246/cl.1982.219

  日期：1982.2.5

  10-Hydroxy-(E)-2-decenoic acid, (E)-2-decenedioic acid (Royal jelly acids), and 9-oxo-(E)-2-decenoic acid (queen substance) were synthesized via 10-hydroxy-3-decenoic acid and 9,9-ethylenedioxy-3-decenoic acid, respectively, prepared easily by the regioselective ring-opening reaction of β-vinyl-β-propiolactone with Grignard reagents in the presence of copper(I) catalyst.

  通过10-羟基合成了10-羟基-(E)-2-癸烯酸、(E)-2-癸烯二酸(蜂王浆酸)和9-氧代-(E)-2-癸烯酸(皇后物质) -3-癸烯酸和 9,9-亚乙基二氧基-3-癸烯酸，分别通过 β-乙烯基-β-丙内酯与格氏试剂在铜（I）催化剂存在下的区域选择性开环反应很容易制备。
• Synthesis of 2-decenedioic acid (royal jelly acid) by sequential carbonylation of butadiene catalyzed by a palladium—phosphine complex and dicobalt octacarbonyl
  作者：Jiro Tsuji、Hideyuki Yasuda

  DOI：10.1016/s0022-328x(00)91365-2

  日期：1977.5

  Carbonylation of butadiene in t-butyl alcohol catalyzed by a palladium complex gave t-butyl-3,8-nonadienoate (I). Further carbonylation of I in methanol with Co2(CO)8 afforded t-butylmethyl-3-decenedioate (II) as the main product. Hydrolysis and base-catalyzed isomerization of II produced E-2-decenedioic acid.

  钯配合物催化丁二烯在叔丁醇中的羰基化，得到3,8-壬二烯酸叔丁酯（I）。I在甲醇中用Co 2（CO）8进一步羰基化，得到-3-癸烯二酸叔丁酯（II）作为主要产物。II的水解和碱催化的异构化产生了E -2-癸二酸。
• [EN] METHOD FOR THE SYNTHESIS OF ALKANE-1-HYDROXY-1,1-DIPHOSPHONIC ACID<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE L'ACIDE ALCANE-1-HYDROXY-1,1-DIPHOSPHONIQUE
  申请人：STRAITMARK HOLDING AG

  公开号：WO2015059287A1

  公开（公告）日：2015-04-30

  The present invention is related to a new method for the synthesis of alkane-1-hydroxy-,1-diphosphonic acid or its salts which includes the steps of -reacting tetraphosphorus hexaoxide and a carboxylic acid under controlled reaction conditions; -hydrolyzing the formed alkane-1-hydroxy-1,1-diphosphonic acid condensates to form alkane-1-hydroxy-1,1-diphosphonic acid; -precipitating the alkane-1-hydroxy-1,1-diphosphonic acid through the use of a suitable solvent; -filtering the alkane-1-hydroxy-1,1-diphosphonic acid and recovering the mother liquor and the suitable solvent.1 The process according to the method of the present invention is highly controllable and is further characterized by a high selectivity.

  本发明涉及一种合成烷基-1-羟基-1,1-二膦酸或其盐的新方法，包括以下步骤：-在控制的反应条件下，将四磷六氧化物和羧酸反应；-水解形成的烷基-1-羟基-1,1-二膦酸缩聚物以形成烷基-1-羟基-1,1-二膦酸；-通过使用适当的溶剂沉淀烷基-1-羟基-1,1-二膦酸；-过滤烷基-1-羟基-1,1-二膦酸并回收母液和适当的溶剂。根据本发明的方法，该过程具有高度可控性，并且具有高选择性。
• PpoC from <i>Aspergillus nidulans</i> is a fusion protein with only one active haem
  作者：Florian Brodhun、Stefan Schneider、Cornelia Göbel、Ellen Hornung、Ivo Feussner

  DOI：10.1042/bj20091096

  日期：2010.2.1

  In Aspergillus nidulans Ppos [psi (precocious sexual inducer)-producing oxygenases] are required for the production of so-called psi factors, compounds that control the balance between the sexual and asexual life cycle of the fungus. The genome of A. nidulans harbours three different ppo genes: ppoA, ppoB and ppoC. For all three enzymes two different haem-containing domains are predicted: a fatty acid haem peroxidase/dioxygenase domain in the N-terminal region and a P450 haem-thiolate domain in the C-terminal region. Whereas PpoA was shown to use both haem domains for its bifunctional catalytic activity (linoleic acid 8-dioxygenation and 8-hydroperoxide isomerization), we found that PpoC apparently only harbours a functional haem peroxidase/dioxygenase domain. Consequently, we observed that PpoC catalyses mainly the dioxygenation of linoleic acid (18:2Δ9Z,12Z), yielding 10-HPODE (10-hydroperoxyoctadecadienoic acid). No isomerase activity was detected. Additionally, 10-HPODE was converted at lower rates into 10-KODE (10-keto-octadecadienoic acid) and 10-HODE (10-hydroxyoctadecadienoic acid). In parallel, decomposition of 10-HPODE into 10-ODA (10-octadecynoic acid) and volatile C-8 alcohols that are, among other things, responsible for the characteristic mushroom flavour. Besides these principle differences we also found that PpoA and PpoC can convert 8-HPODE and 10-HPODE into the respective epoxy alcohols: 12,13-epoxy-8-HOME (where HOME is hydroxyoctadecenoic acid) and 12,13-epoxy-10-HOME. By using site-directed mutagenesis we demonstrated that both enzymes share a similar mechanism for the oxidation of 18:2Δ9Z,12Z; they both use a conserved tyrosine residue for catalysis and the directed oxygenation at the C-8 and C-10 is most likely controlled by conserved valine/leucine residues in the dioxygenase domain.

  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。
• SOME CARBOXYLIC ACIDS PRESENT IN ROYAL JELLY
  作者：William H. Brown、Robert J. Freure

  DOI：10.1139/v59-296

  日期：1959.12.1

  10-hydroxy-2-decenoic acid, has previously been isolated from royal jelly. Small amounts of two additional acids, sebacic and 2-decendioic acid, have now been found in the ether-soluble portion of this special bee foodstuff. Evidence is presented in favor of the trans-configuration for naturally occurring 10-hydroxy-2-decenoic acid. Chromic acid oxidation of the hydroxy acid yields 2-decendioic acid.

  先前仅从蜂王浆中分离出一种羧酸，即 10-羟基-2-癸烯酸。现在已经在这种特殊的蜜蜂食品的醚可溶部分中发现了少量的另外两种酸，癸二酸和 2-癸二酸。有证据支持天然存在的 10-羟基-2-癸烯酸的反式构型。羟基酸的铬酸氧化产生2-癸二酸。