3,4,5-三羟基肉桂酸 | 6093-59-0

• 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
• 中文名称: 3,4,5-三羟基肉桂酸
• 英文名称: 3,4,5-trihydroxycinnamic acid
• 英文别名: (E)-3-(3,4,5-Trihydroxyphenyl)acrylic acid；(E)-3-(3,4,5-trihydroxyphenyl)prop-2-enoic acid
• CAS: 6093-59-0
• 化学式: C₉H₈O₅
• 分子量: 196.16
• InChiKey: ACEAELOMUCBPJP-OWOJBTEDSA-N

物化性质

• 熔点：
  207-208 °C (decomp)
• 沸点：
  501.5±50.0 °C(Predicted)
• 密度：
  1.630±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3,4,5-三羟基肉桂酸 在 咪唑 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  中和新生成的齐墩果烯衍生物的半合成和结构-活性关系

  摘要：

  从（3 S，4 R）-23,28-Dihydroxyolean-12-en-3-yl（2 E）-3-（3,4-dihydroxyphenyl）丙烯酸酯（1 a）中分离出具有显着神经形成活性的传统中草药（Desmodium sambuense）植物。为了确定结构并评估生物活性，我们从市售齐墩果酸中半合成了1 a。小说系列1a然后设计并合成衍生物，以进行结构-活性关系（SAR）研究。所有合成衍生物均通过光谱数据分析进行表征，并在PC12细胞测定中评估了它们的神经生成活性。SAR结果表明，苯环和三萜烯部分上羟基的数量和位置，以及将苯环与三萜烯连接的（饱和或不饱和）烷基链的长度严重影响了神经形成活性。在所有测试的化合物中，发现了1 e [（3 S，4 R）-23,28-dihydroxyolean-12-en-3-yl（2 E）-3-（3,4,5-三羟基苯基）丙烯酸酯]最有效，可在1μm处引起明显的神经突生长。

  DOI：

  10.1002/cmdc.201800352
• 作为产物：
  描述：

  4-香豆酸 在 sodium dihydrogenphosphate 作用下， 反应 0.5h， 生成 3,4,5-三羟基肉桂酸
  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

• Metal-free and base-free decarboxylation of substituted cinnamic acids in a deep eutectic solvent
  作者：Wen-Bing Sheng、Yasmin Sumera、Chen Chen、Ming Zhang、Yuxin Lei、Caiyun Peng、Bin Li、Yuqing Jian、Wei Wang

  DOI：10.1080/00397911.2019.1708945

  日期：2020.2.16

  Abstract A metal-free and base-free strategy was developed in DES to synthesize styrenes for the first time by decarboxylation of cinnamic acid derivatives, which provided a renewable and cost efficiently protocol to access various styrenes including those with functional groups such as 4-vinylphenol and 1-chloro-4-vinylbenzene. GRAPHICAL ABSTRACT

  摘要 在 DES 中开发了一种无金属和无碱的策略，通过肉桂酸衍生物的脱羧作用首次合成苯乙烯，这提供了一种可再生且具有成本效益的协议来获取各种苯乙烯，包括具有 4-乙烯基苯酚等官能团的苯乙烯。和1-氯-4-乙烯基苯。图形概要
• Novel Flavonol Glycosides from the Aerial Parts of Lentil (Lens culinaris)
  作者：Jerzy Żuchowski、Łukasz Pecio、Anna Stochmal

  DOI：10.3390/molecules191118152

  日期：——

  While the phytochemical composition of lentil (Lens culinaris) seeds is well described in scientific literature, there is very little available data about secondary metabolites from lentil leaves and stems. Our research reveals that the aerial parts of lentil are a rich source of flavonoids. Six kaempferol and twelve quercetin glycosides were isolated, their structures were elucidated using NMR spectroscopy and chemical methods. This group includes 16 compounds which have not been previously described in the scientific literature: quercetin 3-O-β-D-glucopyranosyl(1→2)-β-D-galactopyranoside-7-O-β-D-glucuropyranoside (1), kaempferol 3-O-β-D-glucopyranosyl(1→2)-β-D-galacto-pyranoside-7-O-β-D-glucuropyranoside (3), their derivatives 4–10,12–15,17,18 acylated with caffeic, p-coumaric, ferulic, or 3,4,5-trihydroxycinnamic acid and kaempferol 3-O-[(6-O-E-p-coumaroyl)-β-D-glucopyranosyl(1→2)]-α-L-rhamnopyranosyl(1→6)}-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside (11). Their DPPH scavenging activity was also evaluated. This is probably the first detailed description of flavonoids from the aerial parts of lentil.

  尽管科学文献中详细描述了小扁豆（Lens culinaris）种子的植物化学成分，但关于小扁豆叶和茎中次生代谢物的数据非常有限。我们的研究表明，小扁豆的地上部分是黄酮类化合物的丰富来源。我们分离得到了六种山柰酚和十二种槲皮素苷类，通过核磁共振波谱学和化学方法阐明了它们的结构。这一组包括16种化合物，这些化合物先前未在科学文献中被描述过：槲皮素3-O-β-D-吡喃葡萄糖基(1→2)-β-D-吡喃半乳糖苷-7-O-β-D-吡喃葡萄糖苷（1），山柰酚3-O-β-D-吡喃葡萄糖基(1→2)-β-D-吡喃半乳糖苷-7-O-β-D-吡喃葡萄糖苷（3），以及它们的衍生物4-10,12-15,17,18，这些衍生物被咖啡酸、对香豆酸、阿魏酸或3,4,5-三羟基肉桂酸酯化，以及山柰酚3-O-[(6-O-E-对香豆酰基)-β-D-吡喃葡萄糖基(1→2)]-α-L-吡喃鼠李糖基(1→6)}-β-D-吡喃半乳糖苷-7-O-α-L-吡喃鼠李糖苷（11）。我们还评估了它们的DPPH自由基清除活性。这可能是关于小扁豆地上部分黄酮类化合物的首次详细描述。
• Contribution of cinnamic acid analogues in rosmarinic acid to inhibition of snake venom induced hemorrhage
  作者：Hnin Thanda Aung、Tadashi Furukawa、Toshiaki Nikai、Masatake Niwa、Yoshiaki Takaya

  DOI：10.1016/j.bmc.2011.02.013

  日期：2011.4

  rosmarinic acid (1) of Argusia argentea could neutralize snake venom induced hemorrhagic action. Rosmarinic acid (1) consists of two phenylpropanoids: caffeic acid (2) and 3-(3,4-dihydroxyphenyl)lactic acid (3). In this study, we investigated the structural requirements necessary for inhibition of snake venom activity through the use of compounds, which are structurally related to rosmarinic acid (1). By

  在我们之前的文章中，我们报道了Argusia argentea的迷迭香酸（1）可以中和蛇毒引起的大出血作用。迷迭香酸（1）由两种苯基丙醇组成：咖啡酸（2）和3-（3,4-二羟基苯基）乳酸（3）。在这项研究中，我们研究了通过使用与迷迭香酸（1）在结构上相关的化合物来抑制蛇毒活性所必需的结构要求。通过检查对肉桂酸类似物的抗出血活性原矛头flavoviridis（土生）毒液，据透露，在存在ë -烯酸部分（-CHCH–COOH）至关重要。此外，在所测试的化合物中，得出的结论是迷迭香酸（1）（IC 50 0.15μM）是最有效的抗蛇毒抑制剂。
• [EN] NOVEL RESVERATROL ANALOGS<br/>[FR] NOUVEAUX ANALOGUES DE RESVERATROL
  申请人：GOKARAJU GANGA RAJU

  公开号：WO2004000302A1

  公开（公告）日：2003-12-31

  This invention relates to novel resveratrol analogs of the formula given below; wherein R, R1, R2 and R3 are: 1. R=OH, R1=R2=R3=H; 2. R=0H, R1=Br, R2=R3=H; 3. R=R1=0H, R2=R3=H; 4. R=R1=R3=H, R2=3,4,5-trihydroxybenzoyl; 5. R=R1=H, R2=R3=3,4,5-trihydroxybenzoyl; 6. R=R1=R3=H, R2=3,4-dihydroxycinnamoyl; 7. R=R1=R3=H, R2=3,4,5-trihydroxycinnamoyl; 8. R=R1=R3=H, R2=-CH2CH2N(CH3)2; 9. R=R1=R3=H, R2=-COCH2NH2.HC1. These compounds exhibited high antioxidant properties and are useful in food industry and in cosmetics. The compounds may be used in pharmaceutical composition as an antioxidant or free radical scavenger.

  这项发明涉及以下给定公式的新型白藜芦醇类似物；其中R、R1、R2和R3分别为：1. R=OH，R1=R2=R3=H；2. R=OH，R1=Br，R2=R3=H；3. R=R1=OH，R2=R3=H；4. R=R1=R3=H，R2=3,4,5-三羟基苯甲酰基；5. R=R1=H，R2=R3=3,4,5-三羟基苯甲酰基；6. R=R1=R3=H，R2=3,4-二羟基肉桂酰基；7. R=R1=R3=H，R2=3,4,5-三羟基肉桂酰基；8. R=R1=R3=H，R2=-CH2CH2N(CH3)2；9. R=R1=R3=H，R2=-COCH2NH2.HC1。这些化合物表现出较高的抗氧化性能，在食品工业和化妆品中具有用途。这些化合物可以作为抗氧化剂或自由基清除剂在制药组合物中使用。
• Novel resveratrol analogs
  申请人：——

  公开号：US20040209951A1

  公开（公告）日：2004-10-21

  This invention relates to novel resveratrol analogs of the formula given below; wherein R, R 1 , R 2 and R 3 are: 1. R=OH, R 1 =R 2 =R 3 =H; 2. R=OH, R 1 =Br, R 2 =R 3 =H; 3. R=R 1 =OH, R 2 =R 3 =H; 4. R=R 1 =R 3 =H, R 2 =3,4,5-trihydroxybenzoyl; 5. R=R 1 =H, R 2 =R 3 =3,4,5-trihydroxybenzoyl; 6. R=R 1 =R 3 =H, R 2 =3,4-dihydroxycinnamoyl; 7. R=R 1 =R 3 =H, R 2 =3,4,5-trihydroxycinnamoyl; 8. R=R 1 =R 3 =H, R 2 =—CH 2 CH 2 N(CH 3 ) 2 ; 9. R=R 1 =R 3 =H, R 2 =—COCH 2 NH 2 .HCl. These compounds exhibited high antioxidant properties and are useful in food industry and in cosmetics. The compounds may be used in pharmaceutical composition as an antioxidant or free radical scavenger. 1

  这项发明涉及以下给定公式的新型白藜芦醇类似物；其中R、R1、R2和R3分别为：1. R=OH, R1=R2=R3=H；2. R=OH, R1=Br, R2=R3=H；3. R=R1=OH, R2=R3=H；4. R=R1=R3=H, R2=3,4,5-三羟基苯甲酰；5. R=R1=H, R2=R3=3,4,5-三羟基苯甲酰；6. R=R1=R3=H, R2=3,4-二羟基肉桂酰；7. R=R1=R3=H, R2=3,4,5-三羟基肉桂酰；8. R=R1=R3=H, R2=—CH2CH2N(CH3)2；9. R=R1=R3=H, R2=—COCH2NH2.HCl。这些化合物表现出高抗氧化性能，可在食品工业和化妆品中使用。这些化合物可作为抗氧化剂或自由基清除剂用于制药组合物中。