4-[(E)-2-(3-羟基苯基)乙烯基]-1,2-苯二酚 | 70709-66-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 4-[(E)-2-(3-羟基苯基)乙烯基]-1,2-苯二酚
• 中文别名: 2,3,5,6,7,8-六氢-1H-环戊二烯并[b]喹啉-9-胺盐酸
• 英文名称: (E)-1-(3-hydroxyphenyl)-2-(3,4-dihydroxyphenyl)ethene
• 英文别名: 3,4,3'-trihydroxy-trans-stilbene；resveratrol；3,3',4-Trihydroxystilbene；4-[(E)-2-(3-hydroxyphenyl)ethenyl]benzene-1,2-diol
• CAS: 70709-66-9
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: QNVSXXGDAPORNA-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-1-<3-(benzyloxy)phenyl>-2-<3,4-bis(benzyloxy)phenyl>ethene 在 三氯化铝 、 N,N-二甲基苯胺 作用下， 以 二氯甲烷 为溶剂， 以61%的产率得到4-[(E)-2-(3-羟基苯基)乙烯基]-1,2-苯二酚
  参考文献：
  名称：

  Synthesis and protein-tyrosine kinase inhibitory activity of polyhydroxylated stilbene analogs of piceatannol

  摘要：

  A series of hydroxylated trans-stilbenes related to the antileukemic natural product trans-3,3',4,5'-tetrahydroxystilbene (piceatannol) (1) has been prepared and tested for inhibition of the lymphoid cell lineage-specific protein-tyrosine kinase p56lck, which plays an important role in lymphocyte proliferation and immune function. A number of the analogues displayed enhanced enzyme inhibitory activity relative to the natural product. Reduction of the double bond bridging the two aromatic rings and benzylation of the phenolic hydroxyl groups was found to decrease activity significantly. The most potent compounds in the series proved to be trans-3,3',5,5'-tetrahydroxystilbene, trans-3,3',5-trihydroxystilbene, and trans-3,4,4'-trihydroxystilbene.

  DOI：

  10.1021/jm00072a015

文献信息

• [EN] PHOSPHORYLATED POLYPHENOLS AS COLOUR-STABLE AGENTS<br/>[FR] POLYPHENOLS PHOSPHORYLES UTILISES COMME AGENTS DE COULEUR STABLE
  申请人：AJINOMOTO OMNICHEM S A

  公开号：WO2006029483A1

  公开（公告）日：2006-03-23

  The present invention relates to phosphorylated polyphenols, preferably tannins that, unlike their unphosphorylated counterparts, do not suffer from relatively low stability, resulting in an activity that is relatively short in time, and/or that do not result in yellowing of materials therewith such as textiles or polymers. The present invention further relates to a simple, cheap and environmentally friendly way of preparing these compounds. The phosphorylation process of the invention can be extended to simple phenolic compounds as well, as long as these have at least one accessible hydroxyl group. The phosphorylated compounds according to the invention can be used as antioxidants, as radical scavengers, as complexating agents for metals and proteins, as antibacterials or antiallergenic compounds, and as agents to flock textile.

  本发明涉及磷酸化多酚，优选为单宁，与其未磷酸化的对应物不同，它们不会因相对稳定性较低而导致活性时间相对较短和/或不会导致材料变黄，例如纺织品或聚合物。本发明还涉及一种简单、廉价和环保的制备这些化合物的方法。本发明的磷酸化过程也可以扩展到简单的酚类化合物，只要它们至少有一个可接近的羟基。根据本发明磷酸化的化合物可用作抗氧化剂、自由基清除剂、金属和蛋白质络合剂、抗菌或抗过敏化合物以及用于絮凝纺织品的剂。
• [EN] TOPICAL COMPOSITIONS CONTAINING PHOSPHORYLATED POLYPHENOLS<br/>[FR] COMPOSITIONS TOPIQUES CONTENANT DES POLYPHENOLS PHOSPHORYLES
  申请人：AJINOMOTO OMNICHEM S A

  公开号：WO2006029484A1

  公开（公告）日：2006-03-23

  The present invention provides topical compositions containing phosphorylated polyphenols in combination with a topically acceptable carrier. The compositions of the invention provide a means for delayed delivery of the polyphenol to keratinous tissues, such as skin, hair and nails, with enzymes of the keratinous tissue dephosphorylating the polyphenol, and returning it to its native active form. The compositions are particularly useful in the regulation of skin conditions.

  本发明提供了含有磷酸化多酚的局部组成物，与局部可接受的载体相结合。本发明的组成物提供了一种延迟将多酚传递到角质组织（如皮肤、头发和指甲）的手段，角质组织的酶去磷酸化多酚，并将其返回其原生活性形式。该组成物在调节皮肤状况方面特别有用。
• Solid formulations containing resveratrol and omega-3 polyunsaturated fatty acids (n-3 PUFA)
  申请人：SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP2952180A1

  公开（公告）日：2015-12-09

  The present application relates to invention a solid composition comprising omega-3 polyunsaturated fatty acids (n-3 PUFA), or their alkyl esters, and resveratrol, adsorbed on an inert substrate and wherein the recovery of omega-3 is at least 96% after 6 months at 25°C. The composition according to the present invention can be formulated as food supplement or medicament for preventing or treating cardiovascular diseases due to lipid metabolism disorders and increased platelets aggregation; damages due to free radicals selected from the group consisting of atherosclerosis, cancer, inflammatory joint disease, asthma, diabetes, senile dementia and degenerative eye disease; and/or viral diseases.

  本申请涉及一种固体组合物的发明，该组合物包括吸附在惰性基质上的ω-3 多不饱和脂肪酸（n-3 PUFA）或其烷基酯和白藜芦醇，其中ω-3 在 25°C 下 6 个月后的回收率至少为 96%。 根据本发明的组合物可以配制成食品补充剂或药物，用于预防或治疗由于脂质代谢紊乱和血小板聚集增加引起的心血管疾病；由于自由基引起的损害，这些自由基选自由动脉粥样硬化、癌症、炎症性关节病、哮喘、糖尿病、老年痴呆症和退行性眼病；和/或病毒性疾病。
• Formulation and process for modulating wound healing
  申请人：BioMendics, LLC

  公开号：US10426742B2

  公开（公告）日：2019-10-01

  Methods and compounds are disclosed for wound healing by modulating autophagy. A formulation for modulating autophagy comprises a first modulating compound (FAM) selected from compounds having the general structure (I): wherein: L represents a linker selected from —C≡C—, (a tolan), —CH═CH— (a stilbene, preferably trans); or —CRa═CRb— a stilbene derivative; where Ra and Rb are independently H or phenyl optionally substituted with —(R3)p or —(R4)q; R1 to R4 are independent substituents at any available position of the phenyl rings, preferably at 3, 3′, 4, 4′, and/or 5, 5′; and m, n, p, and q are independently 0, 1, 2, or 3 representing the number of substituents of the rings, respectively, but at least one of m or n must be ≥1. Each R1 to R2 is independently selected from substituents described herein, including but not limited to hydroxyl, alkoxy, halo, halomethyl and glycosides. The formulation may also include an auxiliary autophagy modulating compound (AAM) as described herein. The formulation may include a hydrogel formed by the compounds themselves or otherwise and may include salts and/or complexes.

  本发明公开了通过调节自噬促进伤口愈合的方法和化合物。用于调节自噬的制剂包括选自具有一般结构 (I) 的化合物的第一调节化合物 (FAM)： 其中L 代表选自-C≡C-（甲苯）、-CH═CH-（二苯乙烯，最好是反式）或-CRa═CRb-二苯乙烯衍生物的连接体；其中 Ra 和 Rb 独立地是 H 或任选被-(R3)p 或-(R4)q 取代的苯基； R1至R4是独立的取代基，位于苯基环的任何可用位置，优选位于3，3′、4，4′和/或5，5′；m、n、p和q分别独立地为0、1、2或3，代表环的取代基数目，但m或n中至少有一个必须≥1。每个 R1 至 R2 独立地选自本文所述的取代基，包括但不限于羟基、烷氧基、卤代、卤代甲基和苷。制剂还可包括本文所述的辅助自噬调节化合物（AAM）。制剂可包括由化合物本身或以其它方式形成的水凝胶，并可包括盐和/或复合物。
• PHOSPHORYLATED POLYPHENOLS AS COLOUR-STABLE AGENTS
  申请人：Ajinomoto Omnichem S.A.

  公开号：EP1805191A1

  公开（公告）日：2007-07-11