(1a,2a,3b,4b)-2,4-二(4-羟基苯基)-1,3-环丁烷二甲酸 | 490-18-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: (1a,2a,3b,4b)-2,4-二(4-羟基苯基)-1,3-环丁烷二甲酸
• 中文别名: 1,2,3,4-四氢-2-甲基-4-苯基异喹啉-8-胺马来酸酯
• 英文名称: 2α, 4β-bis(4-hydroxyphenyl)cyclobutane-1α,3β-dicarboxylic acid
• 英文别名: 4,4'-dihydroxy-α-truxyillic acid；4,4'-dihydroxy-α-truxillic acid；4,4'-dihydroxytruxillic acid；4,4'-Dihydroxy-α-truxillsaeure；4,4'-Dihydroxy-φ-truxillsaeure；Thezinsaeure
• CAS: 490-18-6
• 化学式: C₁₈H₁₆O₆
• 分子量: 328.321
• InChiKey: LKRJTULSSBSRAS-BIAGXBKMSA-N

物化性质

• 熔点：
  >300 °C(lit.)
• 沸点：
  200-250 °C
• 密度：
  1.487±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  115.06
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1a,2a,3b,4b)-2,4-二(4-羟基苯基)-1,3-环丁烷二甲酸 在 吡啶 、 sodium hydroxide 、 氯化亚砜 作用下， 以 乙醚 、 苯 为溶剂， 反应 5.0h， 生成 1,1'-((1R,2R,3S,4S)-2,4-bis(4-methoxyphenyl)cyclobutane-1,3-diyl)bis(2-diazoethan-1-one)
  参考文献：
  名称：

  Synthesis and antifertility activity of 3,9-dihydroxy-5,6,6a.alpha.,6b.beta.,11,12,12a.beta.,12b.alpha.-octahydrodibenzo[a,g]biphenylene, a structural relative of diethylstilbestrol

  摘要：

  The title diphenol, 1a, was synthesized from p,p'-dihydroxy-alpha-truxillic acid and shown to be active as an oral postcoital antifertility agent in rats: ED100 = 100 (micrograms/kg)/day. The oral uterotropic potency was estimated to be 16% of that of diethylstilbestrol (95% confidence limits of potency 8--35%). The structure of the diphenol, 1a, was confirmed by single-crystal X-ray analysis of the dimethyl ether.

  DOI：

  10.1021/jm00186a023
• 作为产物：
  描述：

  4-香豆酸 以 正己烷 为溶剂， 反应 24.0h， 以980 mg的产率得到(1a,2a,3b,4b)-2,4-二(4-羟基苯基)-1,3-环丁烷二甲酸
  参考文献：
  名称：

  Anti-inflammatory Activities of .ALPHA.-Truxillic Acid Derivatives and Their Monomer Components

  摘要：

  α-特鲁西酸 (1) 和 4,4'-二羟基-α-特鲁西酸 (2) 及其单体成分 (E)-肉桂酸 (3) 和 (E)-p- 的抗炎活性香豆酸 (4) 在福尔马林试验中进行评估。 α-Truxillic Acid (1) 及其衍生物 4,4'-二羟基-α-truxillic Acid (2) 表现出显着的抗炎性疼痛反应活性，而其单体成分 (E)-肉桂酸 (3) 和 (E)-对香豆酸 (4) 没有表现出任何对抗福尔马林诱导的小鼠神经源性或炎症性疼痛反应的活性。这些结果表明二聚体结构可能在抗炎活性的表达中发挥重要作用。此外，为了获得有关其效力的信息，将其抗炎活性与 Incarvillateine (5) 进行了比较，后者含有相同的二聚体结构，并且在福尔马林试验中显示出比吗啡更有效的抗伤害活性。 40mg/kg剂量的α-特鲁西酸(1)和4,4'-二羟基-α-特鲁西酸(2)对抗炎性疼痛反应的活性与20mg/kg剂量的因卡维拉汀相同。

  DOI：

  10.1248/bpb.28.1776

文献信息

• Remarkably high homoselectivity in [2 + 2] photodimerization of trans-cinnamic acids in multicomponent systems
  作者：Thanh Binh Nguyen、Ali Al-Mourabit

  DOI：10.1039/c6pp00201c

  日期：2016.9

  [2 + 2] homoadducts were exclusively obtained with total regio- and stereo-selectivities when a suspension of several solid photoactive trans-cinnamic acids in cyclohexane was stirred and irradiated.

  当搅拌并照射几种固体光敏反式肉桂酸在环己烷中的悬浮液时，[2 + 2]同加合物仅具有总的区域选择性和立体选择性。
• Protein Kinase Inhibitors and Methods for Identiying Same
  申请人：Lawrence S. David

  公开号：US20070254312A1

  公开（公告）日：2007-11-01

  Inhibitors of protein kinase C (PKC)α, PKCδ and PKCζ are provided which are selective for those PKC isotypes. Combinatorial libraries for identifying protein kinases are also provided, as are methods of identifying protein kinases using those libraries. Additionally, methods of treating a mammal having a deleterious condition, where the condition is dependent on a protein kinase for induction or severity, are provided. Methods of inhibiting protein kinases are also provided.

  提供了特异性作用于蛋白激酶C（PKC）α、PKCδ和PKCζ的抑制剂，以及用于识别蛋白激酶的组合化学文库，以及利用这些文库识别蛋白激酶的方法。此外，还提供了用于治疗患有依赖蛋白激酶诱导或严重性的有害状况的哺乳动物的方法。同时还提供了抑制蛋白激酶的方法。
• 4,4′-Dihydroxytruxillic acid as a component of the cell walls of the bambooPhyllostachys edulis
  作者：Sanro Tachibana、Katsumi Ohkubo、G.H. Neil Towers

  DOI：10.1016/0031-9422(91)83010-i

  日期：1992.1

  Abstract 4,4′-Dihydroxytruxillic acid, a photodimer ofp-coumaric acid, as well asp-coumaric and ferulic acids, were identified from alkaline hydrolysates of the cell walls of stems, leaves and shoots of bamboo (Phyllostachys edulis). The truxillic acid content was highest in leaves but was only about 1/1000th that of wall boundp-coumarate. Truxillic acid levels increased on grinding in a Wiley mill

  摘要 从竹子 (Phyllostachys edulis) 茎、叶和枝条细胞壁的碱性水解产物中鉴定出 4,4'-二羟基木瓜酸，一种对香豆酸的光二聚体，以及 asp-香豆酸和阿魏酸。叶中的树胶酸含量最高，但仅为壁结合对香豆酸的 1/1000 左右。在 Wiley 磨机中研磨时增加了 Truxillic 酸水平，这表明它可以通过机械化学能在细胞壁中产生。
• Divaccinosides A–D, four rare iridoid glucosidic truxillate esters from the leaves of Vaccinium bracteatum
  作者：Yong-Mei Ren、Chang-Qiang Ke、Chunping Tang、Sheng Yao、Yang Ye

  DOI：10.1016/j.tetlet.2017.05.013

  日期：2017.6

  Divaccinosides A–D (1–4), four rare iridoid glucoside cyclodimers in the truxillate forms, were characterized from the leaves of Vaccinium bracteatum. They were presumably biosynthesized from two known iridoid glucoside monomers, vaccinoside (5) and 10-O-trans-p-coumaroyl-6α-hydroxyl-dihydromonotropein (6), via a [2+2] cycloaddition reaction. The structures of the new compounds were established by

  Divaccinosides A-d（1 - 4），在truxillate形成四个罕见环烯醚萜甙cyclodimers，从叶，其特征在于乌饭。他们推测，从两个已知环烯醚萜苷的单体，vaccinoside（生物合成5）和10- ø -反式- p -coumaroyl-6 α -羟基- dihydromonotropein（6），通过[2 + 2]环加成反应。通过综合光谱测量，化学转化和单晶X射线晶体学分析，确定了新化合物的结构。
• Three phenolic acid derivatives from stromata of Epichloe typhina on Phleum pratense
  作者：Hiroyuki Koshino、Shun-Ichi Terada、Teruhiko Yoshihara、Sadao Sakamura、Tadayuki Shimanuki、Tohru Sato、Akitoshi Tajimi

  DOI：10.1016/0031-9422(88)80188-2

  日期：1988.1

  Abstract Three new phenolic acid derivatives, 1,3- O -di- trans - p -coumaroylglycerol, 1,2- O -di- trans - p -coumaroylglycerol and chokorin were isolated from stromata of Epichloe typhina on timothy plants Phleum pratense . Their structures were established by spectroscopic and chemical means.

  摘要 从虎尾草属植物Phleum pratense的Epichloe typhina的基质中分离得到3种新的酚酸衍生物1,3-O-二反式-对香豆酰甘油、1,2-O-二反式-对香豆酰甘油和chokorin。它们的结构是通过光谱和化学方法建立的。