3,5-bis(benzyloxy)-4-methylbenzyl alcohol | 99053-60-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-bis(benzyloxy)-4-methylbenzyl alcohol
• 英文别名: [4-methyl-3,5-bis(phenylmethoxy)phenyl]methanol
• CAS: 99053-60-8
• 化学式: C₂₂H₂₂O₃
• 分子量: 334.415
• InChiKey: NKPVZMMZWUCIEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,5-bis(benzyloxy)-4-methylbenzyl alcohol 在 ammonium acetate 、 silica gel 、 铁粉 、 copper(II) nitrate 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 乙酸酐 、 溶剂黄146 、 甲苯 为溶剂， 反应 9.0h， 生成 5,7-bis(benzyloxy)-6-methylindole
  参考文献：
  名称：

  Mechanism and products of autoxidation of 5,7-dihydroxytryptamine

  摘要：

  DOI：

  10.1021/ja00311a065
• 作为产物：
  描述：

  3,5-二羟基-4-甲基苯甲酸 在 lithium aluminium tetrahydride 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 34.58h， 生成 3,5-bis(benzyloxy)-4-methylbenzyl alcohol
  参考文献：
  名称：

  Preparation of Tricyclic Analog as CDE Ring Model of Renieramycin Marine Natural Product by Novel Photo-Induced Transformation of 6-Methoxy-1,2,3,4-Tetrahydroisoquinoline-5,8-dione

  摘要：

  DOI：

  10.3987/com-18-s(f)100

文献信息

• Effect of Methyl Substitution on the Antioxidative Property and Genotoxicity of Resveratrol
  作者：Kiyoshi Fukuhara、Ikuo Nakanishi、Atsuko Matsuoka、Tomohiro Matsumura、Sachiko Honda、Mikiko Hayashi、Toshihiko Ozawa、Naoki Miyata、Shinichi Saito、Nobuo Ikota、Haruhiro Okuda

  DOI：10.1021/tx7003008

  日期：2008.2.1

  Resveratrol (trans- 3,4 ',5-trihydroxystilbene) is a natural phytoalexin with various biological activities including inhibition of lipid peroxidation and free radical scavenging properties. In addition to its beneficial effects, resveratrol also has significant genotoxicity that leads to a high frequency of chromosome aberration together with micronucleus and sister chromatid exchanges. To enhance the radical scavenging activities and to reduce the genotoxicity of resveratrol, we designed 4 '-methyl resveratrol analogues where a methyl group was introduced at the ortho position relative to the 4 '-hydroxy group, which is responsible for both antioxidative activities and genotoxicity of resveratrol. These synthesized methyl analogues of resveratrol showed increased antioxidative activities against galvinoxyl radical as an oxyl radical species. Furthermore, the methyl analogues also surprisingly showed reduced in vitro genotoxicities, suggesting that methyl substitution may improve resveratrol efficacy.