2-hydroxy-4-methoxybenzoic acid 5-hydroxy-4-oxo-4H-pyran-2-ylmethyl ester | 1383106-21-5

• 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: 2-hydroxy-4-methoxybenzoic acid 5-hydroxy-4-oxo-4H-pyran-2-ylmethyl ester
• 英文别名: (5-Hydroxy-4-oxopyran-2-yl)methyl 2-hydroxy-4-methoxybenzoate
• CAS: 1383106-21-5
• 化学式: C₁₄H₁₂O₇
• 分子量: 292.245
• InChiKey: RTCZJUNBAGPFFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  曲酸 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-hydroxy-4-methoxybenzoic acid 5-hydroxy-4-oxo-4H-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Depigmenting activities of kojic acid derivatives without tyrosinase inhibitory activities

  摘要：

  We synthesized benzoate ester derivatives of kojic acid with and without adamantane moiety. Benzoate derivatives 2a-e that did not contain an adamantane moiety showed potent tyrosinase inhibitory activities. However, depigmenting activity was not noted in a cell-based assay. Contrasting results were obtained for benzoate derivatives (3a-e) containing an adamantane moiety. Compounds 3a-e showed potent depigmenting activities without tyrosinase inhibitory activities. To the best of our knowledge, this is the first study showing the depigmenting activities of kojic acid derivatives without tyrosinase inhibitory activities. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.04.046

文献信息

• SALICYLIC ACID DERIVATIVE, METHOD FOR PREPARING SAME, AND COSMETIC COMPOSITION FOR WHITENING COMPRISING SAME
  申请人：AMOREPACIFIC CORPORATION

  公开号：US20180370940A1

  公开（公告）日：2018-12-27

  The present invention relates to a novel salicylic acid derivative, a method for preparing the same, and a cosmetic composition for whitening having the same. The compound exhibits a skin whitening effect by acting on tyrosinase, which is a melanin producing enzyme, to inhibit the production of melanin, and exhibits an improved skin whitening effect compared with kojic acid, alkyl salicylic acid, or alkoxy salicylic acid, which is previously known as a skin whitening agent. Therefore, the compound can be variously applied to cosmetics, preparations for external use, and the like.

  本发明涉及一种新型水杨酸衍生物，一种制备该衍生物的方法，以及具有该衍生物的美白化妆品组合物。该化合物通过作用于黑色素生成酶酪氨酸酶，抑制黑色素的生成，展现了皮肤美白效果，并且与先前已知的皮肤美白剂曲酸、烷基水杨酸或烷氧基水杨酸相比，具有改善的皮肤美白效果。因此，该化合物可以广泛应用于化妆品、外用制剂等领域。
• Depigmenting activities of kojic acid derivatives without tyrosinase inhibitory activities
  作者：Jun-Cheol Cho、Ho Sik Rho、Yung Hyup Joo、Chang Seok Lee、Jaekyoung Lee、Soo Mi Ahn、Jung Eun Kim、Song Seok Shin、Young-Ho Park、Kyung-Do Suh、Soo Nam Park

  DOI：10.1016/j.bmcl.2012.04.046

  日期：2012.6

  We synthesized benzoate ester derivatives of kojic acid with and without adamantane moiety. Benzoate derivatives 2a-e that did not contain an adamantane moiety showed potent tyrosinase inhibitory activities. However, depigmenting activity was not noted in a cell-based assay. Contrasting results were obtained for benzoate derivatives (3a-e) containing an adamantane moiety. Compounds 3a-e showed potent depigmenting activities without tyrosinase inhibitory activities. To the best of our knowledge, this is the first study showing the depigmenting activities of kojic acid derivatives without tyrosinase inhibitory activities. (C) 2012 Published by Elsevier Ltd.