2-methoxylethyl gentisate | 54640-03-8

• 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-methoxylethyl gentisate
• 英文别名: 2-Methoxyethyl 2,5-dihydroxybenzoate
• CAS: 54640-03-8
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: VJIMRWXKHPXUAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙二醇甲醚 、 2,5-二羟基苯甲酸 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 336.0h， 生成 2-methoxylethyl gentisate
  参考文献：
  名称：

  Inhibitors of mammalian melanocyte tyrosinase: in vitro comparisons of alkyl esters of gentisic acid with other putative inhibitors

  摘要：

  To discover safe and effective topical skin-lightening agents, we have evaluated alkyl esters of the natural product gentisic acid (GA), which is related to our lead compound methyl gentisate (MG), and four putative tyrosinase inhibitors, utilizing mammalian melanocyte cell cultures and cell-free extracts. Desirable characteristics include the ability to inhibit melanogenesis in cells (IC50 < 100 mu g/mL) without cytotoxicity, preferably due to tyrosinase inhibition. Of the six esters synthesized, the smaller esters (e.g. methyl and ethyl) were more effective enzyme inhibitors (IC50 similar to 11 and 20 mu g/mL, respectively). For comparison, hydroquinone (HQ), a commercial skin "bleaching" agent, was a less effective enzyme inhibitor (IC50 similar to 72 mu g/mL), and was highly cytotoxic to melanocytes in vitro at concentrations substantially lower than the IC50 for enzymatic inhibition. Kojic acid was a potent inhibitor of the mammalian enzyme (IC50 similar to 6 mu g/mL), but did not reduce pigmentation in cells. Both arbutin and magnesium ascorbyl phosphate were ineffective in the cell-free and eel-based assays. MG at 100 mu g/mL exhibited a minimal inhibitory effect on DHICA oxidase (TRP-1) and no effect on DOPAchrome tautomerase (TRP 2), suggesting that MG inhibits melanogenesis primarily via tyrosinase inhibition. MG and GA were non-mutagenic at the hprt locus in V79 Chinese hamster cells, whereas Ha was highly mutagenic and cytotoxic. The properties of MG in vitro, including (1) pigmentation inhibition in melanocytes, (2) tyrosinase inhibition and selectivity, (3) reduced cytotoxicity relative to HQ, and (4) rack of mutagenic potential in mammalian cells, establish MG as a superior candidate skin-lightening agent. (C) 1999 Elsevier Science Inc.

  DOI：

  10.1016/s0006-2952(98)00340-2

文献信息

• [EN] METHOD OF DEPIGMENTING SKIN AND HAIRS<br/>[FR] PROCEDE DE DEPIGMENTATION DE LA PEAU ET DES CHEVEUX
  申请人：GHISALBERTI CARLO

  公开号：WO2003075882A2

  公开（公告）日：2003-09-18

  The present invention relates to a method of depigmenting human skin and hairs by the topical application of a composition comprising a gentisic acid lower esters with a penetration enhancer in a cosmetically acceptable vehicle.
• Inhibitors of mammalian melanocyte tyrosinase: in vitro comparisons of alkyl esters of gentisic acid with other putative inhibitors
  作者：Ernest V Curto、Cecil Kwong、Heino Hermersdörfer、Hansruedi Glatt、Chie Santis、Victoria Virador、Vincent J Hearing、Thomas P Dooley

  DOI：10.1016/s0006-2952(98)00340-2

  日期：1999.3

  To discover safe and effective topical skin-lightening agents, we have evaluated alkyl esters of the natural product gentisic acid (GA), which is related to our lead compound methyl gentisate (MG), and four putative tyrosinase inhibitors, utilizing mammalian melanocyte cell cultures and cell-free extracts. Desirable characteristics include the ability to inhibit melanogenesis in cells (IC50 < 100 mu g/mL) without cytotoxicity, preferably due to tyrosinase inhibition. Of the six esters synthesized, the smaller esters (e.g. methyl and ethyl) were more effective enzyme inhibitors (IC50 similar to 11 and 20 mu g/mL, respectively). For comparison, hydroquinone (HQ), a commercial skin "bleaching" agent, was a less effective enzyme inhibitor (IC50 similar to 72 mu g/mL), and was highly cytotoxic to melanocytes in vitro at concentrations substantially lower than the IC50 for enzymatic inhibition. Kojic acid was a potent inhibitor of the mammalian enzyme (IC50 similar to 6 mu g/mL), but did not reduce pigmentation in cells. Both arbutin and magnesium ascorbyl phosphate were ineffective in the cell-free and eel-based assays. MG at 100 mu g/mL exhibited a minimal inhibitory effect on DHICA oxidase (TRP-1) and no effect on DOPAchrome tautomerase (TRP 2), suggesting that MG inhibits melanogenesis primarily via tyrosinase inhibition. MG and GA were non-mutagenic at the hprt locus in V79 Chinese hamster cells, whereas Ha was highly mutagenic and cytotoxic. The properties of MG in vitro, including (1) pigmentation inhibition in melanocytes, (2) tyrosinase inhibition and selectivity, (3) reduced cytotoxicity relative to HQ, and (4) rack of mutagenic potential in mammalian cells, establish MG as a superior candidate skin-lightening agent. (C) 1999 Elsevier Science Inc.