2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-ylacetate | 143631-97-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-ylacetate
• 英文别名: 3-Acetoxy-5,7,3',4'-tetrahydroxyflavone；3-O-acetylquercetin；Luteolin acetate；[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl] acetate
• CAS: 143631-97-4
• 化学式: C₁₇H₁₂O₈
• 分子量: 344.277
• InChiKey: ZGBAJCTZRGNZPD-UHFFFAOYSA-N

物化性质

• 沸点：
  641.5±55.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  芦丁 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~80.0 ℃ 、50.0 kPa 条件下， 反应 13.0h， 生成 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-ylacetate
  参考文献：
  名称：

  Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK

  摘要：

  In order to understand the effect of structure-activity relationships on melanogenesis using B16 melanoma cells, 19 quercetin derivatives were synthesized. Among the synthesized compounds, 3-O-methylquercetin (11) and 3',4',7-O-trimethylquercetin (14) increased melanin content more potently than the positive control theophylline, while exhibiting low cytotoxicity. Compound 11 exhibited less melanogenesis-stimulating activity than compound 14. However, 11 increased the expression of tyrosinase and tyrosinase-related protein 1 (TRP-1) to a greater extent than 14, thereby suggesting that melanogenesis in melanoma cells does not depend solely on the expression of the enzymes catalyzing melanin biosynthesis. Furthermore, 14 also stimulated the expression of the microphthalmia-associated transcription factor (MITF) and p-p38 mitogen activated protein kinase (MAPK), while they were not increased by 11. These results suggest that 11 may enhance the expression of tyrosinase and TRP-1 by regulating the proteasomal degradation of melanogenic enzymes and/or by activating other transcriptional factors regulating enzyme expression. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.053

文献信息

• Flavonoid Compounds and Uses Thereof
  申请人：Jarrott Bevyn

  公开号：US20090130051A1

  公开（公告）日：2009-05-21

  Novel flavonoid compounds having anti-oxidant activity are described. The compounds and compositions have been shown to exhibit anti-oxidant properties and are particularly useful in the treatment of ischemia and reperfusion injuries. The invention also describes a method to chemically synthesize such flavonoid compounds and test their efficacy. Such compounds and corresponding pharmaceutically acceptable derivatives and/or salts have uses in the areas of pharmaceuticals, nutraceutical, and veterinary applications.

  本发明描述了具有抗氧化活性的新型黄酮类化合物。这些化合物和组合物已被证明具有抗氧化性质，特别适用于缺血和再灌注损伤的治疗。本发明还描述了一种化学合成这种黄酮类化合物并测试其功效的方法。这些化合物及其对应的药学上可接受的衍生物和/或盐在制药、保健品和兽医应用领域中有用。
• Stabilized retinol for cosmetic dermatological, and pharmaceutical compositions, and use thereof
  申请人：——

  公开号：US20030232091A1

  公开（公告）日：2003-12-18

  The present invention relates to a controlled release system useful to stabilize retinol, retinol derivatives, and extracts containing retinol in cosmetic, dermatological, and pharmaceutical compositions. More specifically, the present invention pertains to stabilized retinol in a solid hydrophobic particle that sustains the release of retinol during the product shelf life and enables a gradual and prolonged release of effective levels of retinol and other cosmetic, dermatological, and pharmaceutical active ingredients into biological surfaces. The present invention also refers to a process of stabilizing retinol, retinol derivatives, and extracts containing retinol in cosmetic, dermatological, and pharmaceutical compositions. The invention further relates to cosmetic, dermatological, and pharmaceutical products comprising stable retinol in a hydrophobic particle that can deliver effective levels of retinol and other cosmetic, dermatological, and pharmaceutical active ingredients to biological surfaces over an extended period of time.

  本发明涉及一种控释系统，用于稳定化妆品、皮肤病学和药物组合物中的视黄醇、视黄醇衍生物和含有视黄醇的提取物。更具体地说，本发明涉及在固体疏水性颗粒中稳定视黄醇，该颗粒可在产品保质期内维持视黄醇的释放，并使有效水平的视黄醇和其他化妆品、皮肤病学和药物活性成分逐渐并长时间地释放到生物表面。本发明还涉及一种稳定化妆品、皮肤病学和药物组合物中的视黄醇、视黄醇衍生物和含有视黄醇的提取物的工艺。本发明还涉及在疏水性颗粒中含有稳定视黄醇的化妆品、皮肤病学和药物产品，该疏水性颗粒可在较长时间内将有效水平的视黄醇和其他化妆品、皮肤病学和药物活性成分输送到生物表面。
• [EN] MEDICAL COMPOUNDS<br/>[FR] COMPOSÉS MÉDICAUX
  申请人：VERA SALUS RICERCA S R L

  公开号：WO2019008537A9

  公开（公告）日：2020-02-20
• Regioselective alcoholysis of flavonoid acetates with lipase in an organic solvent
  作者：Mariapina Natoli、Giovanni Nicolosi、Mario Piattelli

  DOI：10.1021/jo00047a040

  日期：1992.10
• MEDICAL COMPOUNDS
  申请人：Vera Salus Ricerca S.r.l.

  公开号：EP3648759A1

  公开（公告）日：2020-05-13