3,5-di-tert-butyl-4-hydroxycinnamic acid | 22014-01-3

• 物质功能分类: 香精与香料 - 合成香料 - 芳香肉桂酸、酯及衍生物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3,5-di-tert-butyl-4-hydroxycinnamic acid
• 英文别名: 3,5-Di-tert-butyl-4-hydroxycinnamic acid, (E)-；3-(3,5-ditert-butyl-4-hydroxyphenyl)prop-2-enoic acid
• CAS: 22014-01-3
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: CTYWXRDQWMRIIM-UHFFFAOYSA-N

物化性质

• 熔点：
  193-196°C
• 沸点：
  375℃
• 密度：
  1.076
• 闪点：
  195℃
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 稳定性/保质期：
  如果遵照规格使用和储存，则不会分解。避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 安全说明：
  S26,S37
• 危险类别码：
  R36/37/38
• 海关编码：
  2918290000
• 储存条件：
  保持贮藏器密封，并将其放入一个紧密封装的容器中。存储时，请确保放在阴凉、干燥的地方。

制备方法与用途

合成制备方法
用途

反应信息

• 作为反应物：
  描述：

  3,5-di-tert-butyl-4-hydroxycinnamic acid 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以100%的产率得到3-(3,5-二叔丁基-4-羟基苯基)丙酸
  参考文献：
  名称：

  Discovery of a Negative Allosteric Modulator of GABA_B Receptors

  摘要：

  Initialized from the scaffold of CGP7930, an allosteric agonist of GABA(B) receptors, a series of non-competitive antagonists were discovered. Among these compounds, compounds 3, 6, and 14 decreased agonist GABA-induced maximal effect of IP3 production in HEK293 cells overexpressing GABA(B) receptors and Gq(j9) proteins without changing the EC50. Compounds 3, 6, and 14 not only inhibited agonist baclofen-induced ERK1/2 phosphorylation but also blocked CGP7930-induced ERK1/2 phosphorylation in HEK293 cells overexpressing GABA(B) receptors. The results suggested that compounds 3, 6, and 14 are negative allosteric modulators of GABA(B) receptors. The representative compound 14 decreased GABA-induced IP3 production with IC50 of 37.9 mu M and had no effect on other GPCR Class C members such as mGluR1, mGluR2, and mGluRS. Finally, we showed that compound 14 did not bind to the orthosteric binding sites of GABA(B) receptors, demonstrating that compound 14 negatively modulated GABA(B) receptors activity as a negative allosteric modulator.

  DOI：

  10.1021/ml500162z
• 作为产物：
  描述：

  3-(1-Amino-3,5-di-tert-butyl-4-oxo-cyclohexa-2,5-dienyl)-propionic acid 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 生成 3,5-di-tert-butyl-4-hydroxycinnamic acid
  参考文献：
  名称：

  Reaction of 6,8-di-tert-butyl-1-oxaspiro[4.5]deca-5,8-diene-2,7-dione with amines

  摘要：

  DOI：

  10.1007/bf01142808

文献信息

• Inhibitory Activities of Novel Pyrimidine Derivatives on the Contact Hypersensitivity Reaction.
  作者：Yoshiaki Isobe、Masanori Tobe、Yoshifumi Inoue、Yuso Goto、Fumihiro Obara、Masakazu Isobe、Hideya Hayashi

  DOI：10.1248/cpb.51.309

  日期：——

  In order to obtain novel topically applied anti-inflammatory compounds containing an inexpensive anti-oxidative moiety without chirality, we synthesized compound 2c derivatives having a di-tert-butylphenol moiety, and evaluated by topical administration their anti-inflammatory potentials on picryl chloride-(PC) induced contact hypersensitivity reaction (CHR) in mice. In the course of our structure–activity relationship (SAR) studies on the pyrimidine or the anti-oxidative moiety and the linker between them, the most potent compounds (10, 11) were obtained by the insertion of a C2 unit in compound 2c. The potencies of these compounds were 2-fold greater than that of 1. Compounds 10 and 11 were considered to be useful lead compounds having inexpensive anti-oxidative moieties without chirality.

  为了获得含有经济实用的无手性抗氧化基团的新型局部抗炎化合物，我们合成了含二叔丁基苯酚基团的化合物2c衍生物，并通过局部给药在小鼠中评估了它们对接触性超敏反应（CHR）的抗炎潜力，该反应由二硝基氯苯（PC）诱发。在以嘧啶基团或抗氧化基团及其之间的连接链为研究对象的结构活性关系（SAR）研究过程中，通过在化合物2c中插入一个C2单元，得到了效力最强的化合物（10，11）。这些化合物的效力比1号化合物高出2倍。化合物10和11被认为是具有经济实用的无手性抗氧化基团的有用先导化合物。
• Derivatives of 2-(iminomethyl)amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them
  申请人：Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.)

  公开号：US06335445B1

  公开（公告）日：2002-01-01

  A compound selected from the group consisting of a compound of the formula wherein A is selected from the group consisting of and the other substituents are defined in the specification having an inhibitory activity of NO-synthase enzymes producing nitrogen mono-oxide and/or an activity which traps the reactive oxygen species.

  从以下化合物组中选择的一种化合物，其化学式为 其中A是从以下组中选择的 其他取代基在规范中定义，具有抑制NO合酶产生一氧化氮的活性和/或捕获活性氧化物种的活性。
• 2-(iminomethyl) amino-phenyl derivatives, preparation, application as medicines and pharmaceutical compositions containing same
  申请人：Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.)

  公开号：US06340700B1

  公开（公告）日：2002-01-22

  A compound of the formula wherein the substituents are defined as in the specification and their pharmaceutically acceptable salts having NOS and ROS activity.

  该化合物的分子式如下，其中取代基的定义如规范中所述，以及其具有NOS和ROS活性的药用可接受盐。
• Indicator properties of oligoethylene glycol hybrids with sterically hindered phenols
  作者：N. S. Domnina、O. Yu. Sergeeva、E. A. Komarova、M. E. Mikhailova、V. B. Vol’eva、I. S. Belostotskaya、N. L. Komissarova

  DOI：10.1134/s1070428014030129

  日期：2014.3

  (conjugates) formed by polyethylene glycols modified at the terminal hydroxy groups with sterically hindered phenol lose their phase stability at a certain temperature which depends on the molecular weight of polyethylene glycol, structure of sterically hindered phenol, conjugate concentration, and composition of the medium. This property may be used to estimate the effect of structural factors on the hydrophobic-hydrophilic

  由在末端羟基上用位阻酚改性的聚乙二醇形成的杂化化合物（共轭物）的水溶液在一定温度下会失去其相稳定性，这取决于聚乙二醇的分子量，位阻酚的结构，共轭物的浓度和介质的组成。该性质可用于估计结构因素对缀合物-水系统中的疏水-亲水平衡的影响。
• Coupling and fast decarboxylation of aryloxyl radicals of 4-hydroxycinnamic acids with formation of stable p-quinomethanes
  作者：Carmelo Daquino、Mario C. Foti

  DOI：10.1016/j.tet.2005.11.010

  日期：2006.2

  of carboxylic acid groups in the molecules. Kinetic evidence and molecular structures suggest that the formation of these p-quinomethanes is best explained through an 8–8 C–C coupling of the aryloxyl radicals derived from 1 and 2 and a subsequent fast mono- or di-decarboxylation of the initial dimer by an SE1-type mechanism. Further oxidation of the phenolic intermediates by dpph yields the final quinones

  3,5-二叔丁基和3,5-二甲氧基-4-羟基肉桂酸1和2在室温下与dpph的反应自由基在丙酮或其它非羟基极性溶剂收率有趣二聚体p -quinomethanes 10 - 16在可见光区域的特征在于宽的和强的吸收。尽管产量似乎是低到中等（10-40％），这种简单的合成，得到醌没有另外获得，其中含有不饱和γ内酯环（14 - 16）。通过解释ESI-MS，FT-IR和NMR光谱数据已经阐明了结构。特别是，KBr基质中的FT-IR光谱证明了这些化合物的醌性质，因为在1604–1640 cm -1处存在强吸收带并且允许排除分子中羧酸基团的存在。动力学证据和分子结构表明，这些对喹啉甲烷的形成可通过1和2衍生的芳氧基自由基的8-8 C-C偶联以及随后的初始二聚体快速单-或双-脱羧反应得到最好的解释。 S E 1型机制。dpph进一步氧化酚醛中间体 产生最终的醌。