1-(3',4'-dihydroxy)phenyl-6,7-dihydroxy-isochroman | 1383561-20-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-(3',4'-dihydroxy)phenyl-6,7-dihydroxy-isochroman
• 英文别名: 1-(3',4'-dihydroxyphenyl)-6,7-dihydroxyisochroman；1-(3,4-dihydroxyphenyl)-6,7-dihydroxyisochroman；1-(3,4-dihydroxyphenyl)isochroman-6,7-diol；blapsin B；blaspin B；1-(3,4-dihydroxyphenyl)-3,4-dihydro-1H-isochromene-6,7-diol
• CAS: 1383561-20-3；861145-00-8
• 化学式: C₁₅H₁₄O₅
• 分子量: 274.273
• InChiKey: OLEHILHKGHOVLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  羟基酪醇 、 3,4-二羟基苯甲醛 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以84.3%的产率得到1-(3',4'-dihydroxy)phenyl-6,7-dihydroxy-isochroman
  参考文献：
  名称：

  Synthesis and antioxidant evaluation of isochroman-derivatives of hydroxytyrosol: Structure–activity relationship

  摘要：

  Isochroman-derivatives of the natural olive oil phenol hydroxytyrosol (HT) have been synthesised via Oxa-Pictet-Spengler reaction in high yields. Lipophilicity and antioxidant activity were determined to establish the structure-activity relationship of isochromans compared to HT, BHT and alpha-tocopherol. Antioxidant capacity was tested in two different media: bulk oils, using the Rancimat test, and brain homogenates, by measuring malondialdehyde (MDA) levels as a lipoperoxidation biomarker. In addition, other antioxidant assays (FRAP, ABTS and ORAC) were carried out. Rancimat and MDA results show that antioxidant activity was related with lipophilicity, directly in brain homogenates and inversely in the oils, in agreement with the polar paradox. Free o-diphenolic groups positively determined the activity in the oils, whereas reducing and radical-scavenging activities were related to the number of free hydroxyl moieties. BHT and a-tocopherol showed lower antioxidant activity than isochromans and HT. We conclude that HT-isochromans present significant potential as bioactive compounds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2014.10.036

文献信息

• Synthesis and antioxidant evaluation of isochroman-derivatives of hydroxytyrosol: Structure–activity relationship
  作者：Raquel Mateos、Andrés Madrona、Gema Pereira-Caro、Vanessa Domínguez、Rosa M.a Cert、Juan Parrado、Beatriz Sarriá、Laura Bravo、José Luis Espartero

  DOI：10.1016/j.foodchem.2014.10.036

  日期：2015.4

  Isochroman-derivatives of the natural olive oil phenol hydroxytyrosol (HT) have been synthesised via Oxa-Pictet-Spengler reaction in high yields. Lipophilicity and antioxidant activity were determined to establish the structure-activity relationship of isochromans compared to HT, BHT and alpha-tocopherol. Antioxidant capacity was tested in two different media: bulk oils, using the Rancimat test, and brain homogenates, by measuring malondialdehyde (MDA) levels as a lipoperoxidation biomarker. In addition, other antioxidant assays (FRAP, ABTS and ORAC) were carried out. Rancimat and MDA results show that antioxidant activity was related with lipophilicity, directly in brain homogenates and inversely in the oils, in agreement with the polar paradox. Free o-diphenolic groups positively determined the activity in the oils, whereas reducing and radical-scavenging activities were related to the number of free hydroxyl moieties. BHT and a-tocopherol showed lower antioxidant activity than isochromans and HT. We conclude that HT-isochromans present significant potential as bioactive compounds. (C) 2014 Elsevier Ltd. All rights reserved.