3,4,5-trihydroxybenzoic acid-4-hydroxyphenethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4,5-trihydroxybenzoic acid-4-hydroxyphenethyl ester
• 英文别名: 2-(4-hydroxyphenyl)ethyl 3,4,5-trihydroxybenzoate；4-hydroxyphenethyl 3,4,5-trihydroxybenzoate
• 化学式: C₁₅H₁₄O₆
• 分子量: 290.273
• InChiKey: WSPSAXWXELZFQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(4-苯甲氧基苯基)乙醇 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 3,4,5-trihydroxybenzoic acid-4-hydroxyphenethyl ester
  参考文献：
  名称：

  Differential Inhibition of polymerase and Strand-Transfer Activities of HIV-1 Reverse Transcriptase

  摘要：

  A new class of inhibitors of HIV-1 reverse transcriptase obtained by the systematic structural simplification of epicatechin and epigallocatechin gallates are also shown here to inhibit DNA-strand-transfer, a process critical to the completion of the HIV-1-RT reproduction and to recombination-associated mutation of the virus. Up to 80-fold selectivity for DNA-strand-transfer inhibition over polymerase inhibition was observed for a defined subset of these agents. Such specific DNA-strand-transfer inhibitors may have important therapeutic potential. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00827-7

文献信息

• Synthesis and Biological Activities of Tyrosol Phenolic Acid Ester Derivatives
  作者：Hao Zang、Peng Shen、Qian Xu、Luyun Zhang、Guangqing Xia、Jiaming Sun、Junyi Zhu、Xiaohong Yang

  DOI：10.1007/s10600-019-02889-z

  日期：2019.11

  Sixteen tyrosol derivatives were synthesized and characterized by NMR and HR-MS. The antioxidant activity of those compounds was evaluated using four different assays. The results showed that some target compounds displayed better antioxidant activity than L-ascorbic acid and Trolox. Five target compounds exhibited more potent α-glucosidase inhibition activity (18.1–56.7 μM) than acarbose (60.9 μM). Eight target compounds showed some anticholinesterase activities.

  合成并表征了十六种酪醇衍生物，采用NMR和高分辨质谱（HR-MS）进行检测。这些化合物的抗氧化活性通过四种不同的测定方法进行评估。结果表明，一些靶向化合物的抗氧化活性优于L-抗坏血酸和Trolox。五种靶向化合物展现出比阿卡波糖更强的α-葡萄糖苷酶抑制活性（18.1–56.7 μM），而阿卡波糖的活性为60.9 μM。有八种靶向化合物显示出一定的抗胆碱酯酶活性。
• 酪醇酚酸酯类化合物的制备方法和应用
  申请人：通化师范学院

  公开号：CN109232255A

  公开（公告）日：2019-01-18

  本发明公开了酪醇酚酸酯类化合物的制备方法和应用，属于生物医药技术领域，对酪醇的化学结构进行了衍生化，在其结构中引入了酚酸，其结构与酪醇相比有较大差异，且具有较好的抗氧化作用。本发明还提供了酪醇酚酸酯的制备方法，即以酪醇、三苯基磷和酚酸为原料，氮气保护下加入四氢呋喃，冰浴下滴加偶氮二甲酸二异丙酯，反应后经柱层析即得酪醇酚酸酯类化合物。本制备方法操作简单，不需要对酚酸和酪醇的酚羟基进行保护与脱保护，一步反应得到目标化合物，收率较高，环境友好，本发明公开的酪醇酚酸酯用于抗氧化作用。
• Synthetic tyrosyl gallate derivatives as potent melanin formation inhibitors
  作者：Chan Woo Lee、Eun-Mi Son、Han Sung Kim、Pan Xu、Tuyagerel Batmunkh、Burm-Jong Lee、Kyung Ah Koo

  DOI：10.1016/j.bmcl.2007.07.032

  日期：2007.10

  Three tyrosyl gallate derivatives (1-3) with variable hydroxyl substituent at the aromatic ring of tyrosol were synthesized and evaluated as potent inhibitors on tyrosinase activity and melanin formation in melan-a cells. Among three tyrosyl gallate derivatives, 4-hydroxyphenethyl 3,4,5-trihydroxybenote (1) (IC50 = 4.93 mu M), 3-hydroxyphenethyl 3,4,5-trihydroxybenote (2) (IC50 = 15.21 mu M), and 2-hydroxyphenethyl 3,4,5-trihydroxybenote (3) (IC50 = 14.50 mu M) exhibited significant inhibitory effect on tyrosinase activity. Compound 1 was the most active compound, though it did not show the inhibitory effect on melanin formation in melan-a cells. However, compounds 2 (IC50 = 8.94 mu M) and 3 (IC50 = 13.67 mu M) significantly suppressed the cellular melanin formation without cytotoxicity. This study shows that the position of hydroxyl substituent at the aromatic ring of tyrosol plays an important role in the intracellular regulation of melanin formation in cell-based assay system. (C) 2007 Elsevier Ltd. All rights reserved.
• [EN] GALLIC ACID ESTERS AND COMPOSITIONS COMPRISING THEREOF<br/>[FR] ESTERS D'ACIDE GALLIQUE ET COMPOSITIONS COMPRENANT CEUX-CI
  申请人：GHISALBERTI CARLO

  公开号：WO2008065527A2

  公开（公告）日：2008-06-05

  [EN] Gallates formed by condensation of gallic acid with a hydroxyl-containing fragrance for the use in a composition suitable for disinfecting and seboregulating purposes.
  [FR] L'invention concerne des gallates formés par condensation d'acide gallique avec une fragrance contenant un groupe hydroxyle, destinés à être utilisés dans une composition désinfectante et séborégulatrice.
• Differential Inhibition of polymerase and Strand-Transfer Activities of HIV-1 Reverse Transcriptase
  作者：L.M.Viranga Tillekeratne、Angela Sherette、Jennifer A Fulmer、Lynn Hupe、Donald Hupe、Sam Gabbara、James A Peliska、Richard A Hudson

  DOI：10.1016/s0960-894x(01)00827-7

  日期：2002.2

  A new class of inhibitors of HIV-1 reverse transcriptase obtained by the systematic structural simplification of epicatechin and epigallocatechin gallates are also shown here to inhibit DNA-strand-transfer, a process critical to the completion of the HIV-1-RT reproduction and to recombination-associated mutation of the virus. Up to 80-fold selectivity for DNA-strand-transfer inhibition over polymerase inhibition was observed for a defined subset of these agents. Such specific DNA-strand-transfer inhibitors may have important therapeutic potential. (C) 2002 Elsevier Science Ltd. All rights reserved.