Cyanomethyl 1,4-dihydroxynaphthalene-2-carboxylate | 1119487-57-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Cyanomethyl 1,4-dihydroxynaphthalene-2-carboxylate
• CAS: 1119487-57-8
• 化学式: C₁₃H₉NO₄
• 分子量: 243.219
• InChiKey: JMJANWWLQGNPCD-UHFFFAOYSA-N

物化性质

• 沸点：
  559.3±40.0 °C(predicted)
• 密度：
  1.446±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Cyanomethyl 1,4-dihydroxynaphthalene-2-carboxylate 、 维生素A 在 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl 1,4-dihydroxy-2-naphthoate
  参考文献：
  名称：

  Synthesis and in vitro biological activity of retinyl polyhydroxybenzoates, novel hybrid retinoid derivatives

  摘要：

  A new hybrid derived from retinol was designed to improve the stability and anti-oxidant activity of retinol and also to add whitening properties besides its usual anti-aging properties. A variety of polyhydroxybenzoates of retinol were prepared either by base-catalysis or by direct esterification of retinol and screened for such desirable properties by analyzing the in vitro biological activity of the hybrids. Some of the retinol derivatives enhanced their thermal stability and decreased photosensitivity, and exhibited an activity in collagen synthesis similar to that of retinol. In addition, the retinyl gallate 6 showed higher activities in free radical scavenging and melanogenesis inhibition than retinol. Thus, owing to its excellent stabilities, retinyl gallate 6 may be conveniently used not only as an additive for cosmetics for prevention and improvement of skin aging and whitening but also as medicine for the treatment of skin troubles. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.028

文献信息

• Synthesis and in vitro biological activity of retinyl polyhydroxybenzoates, novel hybrid retinoid derivatives
  作者：Sungbum Kim、Youngmin Kim、Younggyu Kong、Hyojung Kim、Jahyo Kang

  DOI：10.1016/j.bmcl.2008.11.028

  日期：2009.1

  A new hybrid derived from retinol was designed to improve the stability and anti-oxidant activity of retinol and also to add whitening properties besides its usual anti-aging properties. A variety of polyhydroxybenzoates of retinol were prepared either by base-catalysis or by direct esterification of retinol and screened for such desirable properties by analyzing the in vitro biological activity of the hybrids. Some of the retinol derivatives enhanced their thermal stability and decreased photosensitivity, and exhibited an activity in collagen synthesis similar to that of retinol. In addition, the retinyl gallate 6 showed higher activities in free radical scavenging and melanogenesis inhibition than retinol. Thus, owing to its excellent stabilities, retinyl gallate 6 may be conveniently used not only as an additive for cosmetics for prevention and improvement of skin aging and whitening but also as medicine for the treatment of skin troubles. (C) 2008 Elsevier Ltd. All rights reserved.