2,4-(E,E)-tetradecadienoic acid | 24738-49-6

• 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: 2,4-(E,E)-tetradecadienoic acid
• 英文别名: (2E,4E)-tetradecadienoic acid；(2E,4E)-tetradeca-2,4-dienoic acid；trans,trans-2,4-tetradecadienoic acid；2E,4E-tetradecadienoic acid
• CAS: 24738-49-6
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: WNLVXSRACLAFOL-AQASXUMVSA-N

物化性质

• 熔点：
  54 - 56°C
• 沸点：
  354.8±11.0 °C(Predicted)
• 密度：
  0.929±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  2,4-(E,E)-tetradecadienoic acid 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 trans,trans-2,4-tetradecadienoic acid chloride
  参考文献：
  名称：

  A Synthetic Approach to Natural Dienamides of Insecticidal Interest

  摘要：

  An efficient synthesis of dienamides of insecticidal interest has been stereoselectively achieved featuring a Stille cross-coupling reaction as the key step.

  DOI：

  10.1080/00397919808005717
• 作为产物：
  描述：

  Methyl 2-tetradecynoate 在 三苯基膦 、 sodium hydroxide 、 苯酚 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 52.0h， 生成 2,4-(E,E)-tetradecadienoic acid
  参考文献：
  名称：

  Bungeanool、Isobungeanool、Dihydrobungeanool、Tetrahydrobungeanool、Hazaleamide、Lanyuamide III 和类似物的合成

  摘要：

  花椒是从花椒果皮中分离得到的一族醇酰胺类天然产物，在结构上与花椒有亲缘关系。虽然 sanshools，尤其是羟基-α-sanshool，已在各种背景下进行了研究，但关于 bungeanools 的研究却非常有限。为了促进他们的研究，我们通过使用也适用于合成类似物的灵活路线开发了该化合物家族所有四个成员的立体选择性合成。合成中的关键转化是立体选择性三苯基膦/苯酚催化的炔酸酯异构化为相应的共轭 E,E-二烯酸酯。

  DOI：

  10.1055/a-1653-4050

文献信息

• Structure-antitumor Activity Relationship of Semi-synthetic Spicamycin Derivatives.
  作者：TERUYUKI SAKAI、HIROYUKI KAWAI、MASARU KAMISHOHARA、ATSUO ODAGAWA、AKASHI SUZUKI、TAKESHI UCHIDA、TOMIKO KAWASAKI、TAKASHI TSURUO、NOBORU OTAKE

  DOI：10.7164/antibiotics.48.1467

  日期：——

  New derivatives of spicamycin modified at the fatty acid moieties of the molecule were synthesized and their structure-activity relationships were examined. The antitumor activity was greatly influenced by modification of the fatty acid moieties to tetradecadienoyl or dodecadienoyl analogues exhibiting better antitumor activity against COL-1 human colon cancer xenograft than SPM VIII.

  新合成了一系列在分子脂肪酸部分进行了修饰的斯匹卡霉素衍生物，并研究了它们的构效关系。通过对脂肪酸部分进行修饰，将其转化为十四碳二烯酸或十二碳二烯酸类似物，这些衍生物对COL-1人结肠癌异种移植模型的抗肿瘤活性显著优于SPM VIII。
• Amides of vegetable origin. Part XII. A new series of alka-2,4-dienoic tyramine-amides from Anacyclus pyrethrum D.C. (Compositae)
  作者：R. S. Burden、L. Crombie

  DOI：10.1039/j39690002477

  日期：——

  Anacyclus pyrethrum D.C. (Compositae) contains N-(2′-p-hydroxyphenylethyl) deca-, dodeca-, and tetradeca-trans-2, trans-4-dienamide, a new series of tyramine amides corresponding to isobutylamides which this plant produces. The tyramides, and the corresponding isobutylamides, are synthesised stereospecifically by phosphonatenaion synthesis. Anacyclus pyrethrum is found to contain the lignan (+)-sesamin and attention is drawn to the cooccurrence of lipid (and other) amides with lignans in a number of plants from three families (Compositae, Piperaceae, and Rutaceae).

  安卡菊（Anacyclus pyrethrum D.C.，菊科）含有新系列的酪胺酰胺，即N-(2′-对羟基苯乙基)癸基、十二基和十四基反式-2,反式-4-二烯酰胺，这些化合物对应于该植物产生的异丁基酰胺。酪胺酰胺及其相应的异丁基酰胺是通过磷酸钠特定的立体选择性合成得到的。研究发现，安卡菊中还含有木脂素（+）-芝麻素，并指出在来自三个科（菊科、胡椒科和芸香科）的多种植物中，脂质（及其他）酰胺与木脂素的共存现象值得关注。
• Synthesis of the fatty acid of pramanicin
  作者：Christopher Cow、David Valentini、Paul Harrison

  DOI：10.1139/v97-106

  日期：1997.6.1

  The natural product tetradec-2-enoic acid-4,5-epoxide (2), which is also a component of the antibiotic pramanicin (1), was prepared in racemic form by a glycoluril-template directed approach. Two sequential additions of acetate units to decanoic acid are effected by intramolecular condensations on the template, mimicking the proposed biosynthetic pathway to 1. Cleavage of the grown trans,trans-tetradeca-2,4-dienoyl chain from the template and epoxidation yields 2. The reaction sequence illustrates the applicability of this biomimetic approach to total synthesis of natural products. Keywords: pramanicin, biomimetic, glycoluril, template.

  天然产物十四碳烯酸-4,5-环氧化物(2)，也是抗生素普拉曼霉素(1)的组分之一，通过一种以甘氨酰脲为模板的方向性方法制备了其外消旋形式。在模板上，通过分子内缩合反应模拟了到1的生物合成途径，将乙酸基单位顺序加入癸酸分子中。从模板上割离生长的反式、反式-四十二碳二烯酰链并环氧化，得到2。这个反应序列说明了这种仿生方法在天然产物的全合成中的适用性。关键词：普拉曼霉素、仿生、甘氨酰脲、模板。
• DISPERSION AND METHOD FOR FORMING HYDROGEL
  申请人：NISSAN CHEMICAL INDUSTRIES, LTD.

  公开号：US20160129119A1

  公开（公告）日：2016-05-12

  An object is to provide dispersion containing lipid peptide type compound useful as low molecular weight gelator, such as lipid dipeptide and lipid tripeptide, and dissolution accelerator capable of dissolving the lipid peptide type compound at lower temperature and more easily. It is also an object to provide dispersion that can form hydrogel by simpler method and under milder condition (low temperature) and from which gel can be obtained as gel having high thermal stability, and provide method for forming the gel. Dispersion including: a lipid peptide type compound in which peptide portion formed by repetition of at least two or more identical or different amino acids is bonded to lipid portion including C 10-24 aliphatic group; dissolution accelerator having, in molecules thereof, hydrophilic portion and hydrophobic portion, the hydrophilic portion having betaine structure; and water; and method for producing hydrogel by use of the dispersion.

  本发明旨在提供一种包含脂肽类化合物的分散体，该化合物可用作低分子量凝胶剂，例如脂肽二肽和脂肽三肽，并且提供一种溶解加速剂，该加速剂能够在较低温度和更容易地溶解脂肽类化合物。本发明还旨在提供一种能够通过更简单的方法在较温和的条件下（低温）形成水凝胶的分散体，并从中可以得到具有高热稳定性的凝胶，并提供形成凝胶的方法。包括以下成分的分散体：脂肽类化合物，其中由至少两个或更多相同或不同的氨基酸重复形成的肽部分与包括C10-24脂肪族基团的脂肪部分相结合；溶解加速剂，其分子中具有亲水部分和疏水部分，亲水部分具有甜菜碱结构；和水；以及利用该分散体制备水凝胶的方法。
• TRANSDERMALLY ABSORBABLE BASE MATERIAL CONTAINING LIPID PEPTIDE COMPOUND
  申请人：KYUSHU UNIVERSITY

  公开号：US20180021250A1

  公开（公告）日：2018-01-25

  A transdermally absorbable base material including: a lipid peptide compound including at least one of compound of Formula (1) below and the similar compounds or pharmaceutically usable salts thereof; a surfactant; a specific polyhydric alcohol; a fatty acid; and water, wherein R 1 is a C 9-23 aliphatic group; R 2 is a hydrogen atom or a C 1-4 alkyl group that optionally has a branched chain having a carbon atom number of 1 or 2; R 3 is a —(CH 2 ) n —X group; n is a number of 1 to 4; and X is amino group, guanidino group, —CONH 2 group, or a 5-membered cyclic group optionally having 1 to 3 nitrogen atoms, a 6-membered cyclic group optionally having 1 to 3 nitrogen atoms, or a condensed heterocyclic group constituted by a 5-membered cyclic group and a 6-membered cyclic group which optionally have 1 to 3 nitrogen atoms.

  一种可经皮吸收的基础材料，包括：脂肽化合物，其中包括下式（1）的化合物之一及其类似化合物或药用可用盐；表面活性剂；特定的多羟基醇；脂肪酸；和水。其中，R1是C9-23脂肪族基；R2是氢原子或C1-4烷基，可选地具有碳原子数为1或2的支链；R3是-（CH2）n-X基团；n为1至4的数字；X是氨基团，鸟氨酸基团，-CONH2基团，或者是一个可选地具有1至3个氮原子的5元环基团，可选地具有1至3个氮原子的6元环基团，或者是由一个5元环基团和一个6元环基团组成的缩合杂环基团，可选地具有1至3个氮原子。