3-(3,4,5-三羟基苯基)丙酸 | 40284-59-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: 3-(3,4,5-三羟基苯基)丙酸
• 英文名称: 3-(2,3,4-trihydroxyphenyl)propanoic acid
• 英文别名: 3-(3,4,5-trihydroxyphenyl)propanoic acid；β-<3,4,5-Trimethoxy-phenyl>-propionsaeure；3.4.5-Trihydroxy-phenyl-propionsaeure
• CAS: 40284-59-1
• 化学式: C₉H₁₀O₅
• 分子量: 198.175
• InChiKey: FWFVXNQOVGSSHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3,4,5-三羟基苯基)丙酸 在 palladium on activated charcoal 、 氢气 、 二异丁基氢化铝 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.0h， 生成 2-[hexyl(dimethyl)azaniumyl]ethyl 3-(3,4,5-trihydroxyphenyl)propyl phosphate
  参考文献：
  名称：

  [EN] PHOTO-CLEAVABLE PRIMER COMPOSITIONS AND METHODS OF USE
  [FR] COMPOSITIONS D'AMORCES PHOTOCLIVABLES ET PROCÉDÉ D'UTILISATION

  摘要：

  在一种实施例中，本申请公开了一种具有化学式I和化学式II的光解离表面结合化合物：其中变量EG、EG1、SP1、SP2、SP3、Ar和BG的定义如本文所述。在另一种实施例中，该申请公开了一种利用该表面结合化合物在基板表面形成涂层的方法。

  公开号：

  WO2017132484A1
• 作为产物：
  描述：

  3,4-二羟基苯基丙酸 在 sodium dihydrogenphosphate 作用下， 反应 0.25h， 以85%的产率得到3-(3,4,5-三羟基苯基)丙酸
  参考文献：
  名称：

  p-Hydroxyphenylacetate 3-Hydroxylase as a Biocatalyst for the Synthesis of Trihydroxyphenolic Acids

  摘要：

  Trihydroxyphenolic acids such as 3,4,5-trihydroxycinnamic acid (3,4,5-THCA) 4c and 2-(3,4,5-trihydroxyphenyl)acetic acid (3,4,5-THPA) 2c are strong antioxidants that are potentially useful as medicinal agents. Our results show that p-hydroxyphenylacetate (HPA) 3-hydroxylase (HPAH) from Acinetobacter baumannii can catalyze the syntheses of 3,4,5-THPA 2c and 3,4,5-THCA 4c from 4-HPA 2a and p-coumaric acid 4a, respectively. The wild-type HPAH can convert 4-HPA 2a completely into 3,4,5-THPA 2c within 100 min (total turnover number (TTN) of 100). However, the wild-type enzyme cannot efficiently synthesize 3,4,5-THCA 4c. To improve the efficiency, the oxygenase component of HPAH (C-2) was rationally engineered in order to maximize the conversion of p-coumaric acid 4a to 3,4,5-THCA 4c. Results from site-directed mutagenesis studies showed that Y398S is significantly more effective than the wildtype enzyme for the synthesis of 3,4,5-THCA 4c; it can catalyze the complete bioconversion of p-coumaric acid 4a to 3,4,5-THCA 4c within 180 min (TTN similar to 23 at 180 min). The yield and stability of 3,4,5-THPA 2c and 3,4,5-THCA 4c were significantly improved in the presence of ascorbic acid. Thermostability studies showed that the wild-type C-2 was very stable and remained active after incubation at 30, 35, and 40 degrees C for 24 h. Y398S was moderately stable because its activity was retained for 24 h at 30 degrees C and for 15 h at 35 degrees C. Transient kinetic studies using stopped-flow spectrophotometry indicated that the key improvement in the reaction of Y398S with p-coumaric acid 4a lies within the protein-ligand interaction. Y398S binds to p-coumaric acid 4a with higher affinity than the wild-type enzyme, resulting in a shift in equilibrium toward favoring the productive coupling path instead of the path leading to wasteful flavin oxidation.

  DOI：

  10.1021/acscatal.5b00439

文献信息

• [EN] SURFACE PRIMER COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSITIONS DE COUCHE PRIMAIRE DE SURFACE ET PROCÉDÉ D'UTILISATION
  申请人：ACATECHOL INC

  公开号：WO2017132463A1

  公开（公告）日：2017-08-03

  In one embodiment, the present application discloses a surface binding compound of the Formula I or Formula II: wherein the variables EG, EG1, SP1, SP2, SP3, Ar and BG are as defined herein. In another embodiment, the application discloses a method for forming a coating on a surface of a substrate using the surface binding compound of the Formula I or Formula II.

  在一个实施例中，本申请公开了一种Formula I或Formula II的表面结合化合物，其中变量EG、EG1、SP1、SP2、SP3、Ar和BG的定义如本文所述。在另一个实施例中，该申请公开了一种利用Formula I或Formula II的表面结合化合物在基板表面形成涂层的方法。
• Antioxidants
  申请人：Rudolph Thomas

  公开号：US20080152603A1

  公开（公告）日：2008-06-26

  The present invention relates to the use of compounds of the formula (I), with radicals defined in the description, as antioxidants, to corresponding novel compounds and compositions, and to corresponding processes for the preparation of compounds and compositions.

  本发明涉及使用式(I)中定义的基团化合物作为抗氧化剂，涉及对应的新型化合物和组合物，以及制备这些化合物和组合物的对应过程。
• Uv Protection
  申请人：Rudolph Thomas

  公开号：US20080171004A1

  公开（公告）日：2008-07-17

  The present invention relates to the use of compounds which do not themselves exhibit significant UV absorption in the UV-A or UV-B region, but are reactive under use conditions, for the development of UV-A or UV-B protection during use, to corresponding novel compounds and compositions, and to corresponding processes for the preparation of compounds and compositions.

  本发明涉及使用那些本身在UV-A或UV-B区域不表现出显著UV吸收但在使用条件下具有反应性的化合物用于开发UV-A或UV-B保护，以及相应的新化合物和组合物，以及制备化合物和组合物的相应过程。
• Surface primer compositions and methods of use
  申请人：ACatechol, Inc.

  公开号：US10696698B2

  公开（公告）日：2020-06-30

  In one embodiment, the present application discloses a surface binding compound of the Formula I or Formula II: wherein the variables EG, EG1, SP1, SP2, SP3, Ar and BG are as defined herein. In another embodiment, the application discloses a method for forming a coating on a surface of a substrate using the surface binding compound of the Formula I or Formula II.

  在一个实施方案中，本申请公开了一种式 I 或式 II 的表面结合化合物： 其中变量 EG、EG1、SP1、SP2、SP3、Ar 和 BG 如本文所定义。在另一个实施方案中，本申请公开了一种使用式 I 或式 II 的表面结合化合物在基底表面形成涂层的方法。
• Photo-cleavable primer compositions and methods of use
  申请人：ACatechol, Inc.

  公开号：US10689407B2

  公开（公告）日：2020-06-23

  In one embodiment, the present application discloses a photo-cleavable surface binding compound of the Formula I and Formula II: wherein the variables EG, EG1, SP1, SP2, SP3, Ar and BG are as defined herein. In another embodiment, the application discloses a method for forming a coating on a surface of a substrate using the surface binding compound.

  在一个实施方案中，本申请公开了一种式 I 和式 II 的光可裂解表面结合化合物： 其中变量 EG、EG1、SP1、SP2、SP3、Ar 和 BG 如本文所定义。在另一个实施方案中，本申请公开了一种使用表面结合化合物在基底表面形成涂层的方法。