2,3-dimethyl-5-<(2-methyl)-2-propenyl>hydroquinone | 53959-83-4

• 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: 2,3-dimethyl-5-<(2-methyl)-2-propenyl>hydroquinone
• 英文别名: 2,3-Dimethyl-5-(2-methyl-2-propenyl)-hydrochinon；2,3-Dimethyl-5-(2-methylprop-2-enyl)benzene-1,4-diol；2,3-dimethyl-5-(2-methylprop-2-enyl)benzene-1,4-diol
• CAS: 53959-83-4
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: YREQJQSJCSMVBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dimethyl-5-<(2-methyl)-2-propenyl>hydroquinone 在 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 以91%的产率得到2,3-dihydro-2,2,6,7-tetramethylbenzofuran-5-ol
  参考文献：
  名称：

  A rapid screening test to determine the antioxidant potencies of natural and synthetic antioxidants

  摘要：

  This paper presents a simple and convenient method for measuring antioxidant efficiencies in a model system consisting of micelles of sodium dodecyl sulfate (SDS) with added linoleic acid. The analytical method involves following the development of absorption at 234 nm due to the conjugated diene hydroperoxide of linoleic acid; 2,2'-azobis(2-amidinopropane) dihydrochloride (ABAP) is used as the initiator. The antioxidant efficiency of an antioxidant is defined as AE = k(inh)/k(p), where k(inh) is the rate constant for reaction of the peroxyl radical from linoleic acid with the antioxidant (eq 7 in the text) and k(p) is the propagation rate constant for autoxidation of linoleic acid (eq 5). The relative antioxidant efficiency (RAE) is defined as the AE of the test compound divided by that for alpha-tocopherol; thus, RAE values are equal to k(inh)/k(inh,alpha-tocopherol). Since the absolute value of the rate constant for reaction of alpha-tocopherol with peroxyl radicals is known in micellar systems, the absolute value of k(inh) for a given antioxidant can be calculated if required. To establish the reliability of the method we report the AE of 17 synthetic and naturally occurring antioxidants and compare values obtained by this method to others in the literature. For neutral antioxidants, the same AE values are obtained in both negatively-charged micelles of SDS and positively-charged micelles of hexadecyl trimethylammonium bromide (HDTBr). The relative antioxidant efficiencies are reported for more than 40 synthetic compounds that are potential antioxidants or anti-inflammatory compounds; most of these compounds are tocopherol, ascorbate, or 2-hydroxytetronic acid analogues. Although the charge type of the micelle has no effect on the RAE of neutral antioxidants, micelles of different charge types do have an effect on the RAE value of charged antioxidants such as ascorbic acid, other 2-hydroxytetronic acids, and Trolox C. In 0.10 M SDS micelles, ascorbic acid and alpha-tocopherol are shown to have an additive effect, not a synergistic effect, as antioxidants.

  DOI：

  10.1021/jo00065a013
• 作为产物：
  描述：

  2,3-二甲基-1,4-苯醌 在 potassium carbonate 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 88.0h， 生成 2,3-dimethyl-5-<(2-methyl)-2-propenyl>hydroquinone
  参考文献：
  名称：

  A rapid screening test to determine the antioxidant potencies of natural and synthetic antioxidants

  摘要：

  This paper presents a simple and convenient method for measuring antioxidant efficiencies in a model system consisting of micelles of sodium dodecyl sulfate (SDS) with added linoleic acid. The analytical method involves following the development of absorption at 234 nm due to the conjugated diene hydroperoxide of linoleic acid; 2,2'-azobis(2-amidinopropane) dihydrochloride (ABAP) is used as the initiator. The antioxidant efficiency of an antioxidant is defined as AE = k(inh)/k(p), where k(inh) is the rate constant for reaction of the peroxyl radical from linoleic acid with the antioxidant (eq 7 in the text) and k(p) is the propagation rate constant for autoxidation of linoleic acid (eq 5). The relative antioxidant efficiency (RAE) is defined as the AE of the test compound divided by that for alpha-tocopherol; thus, RAE values are equal to k(inh)/k(inh,alpha-tocopherol). Since the absolute value of the rate constant for reaction of alpha-tocopherol with peroxyl radicals is known in micellar systems, the absolute value of k(inh) for a given antioxidant can be calculated if required. To establish the reliability of the method we report the AE of 17 synthetic and naturally occurring antioxidants and compare values obtained by this method to others in the literature. For neutral antioxidants, the same AE values are obtained in both negatively-charged micelles of SDS and positively-charged micelles of hexadecyl trimethylammonium bromide (HDTBr). The relative antioxidant efficiencies are reported for more than 40 synthetic compounds that are potential antioxidants or anti-inflammatory compounds; most of these compounds are tocopherol, ascorbate, or 2-hydroxytetronic acid analogues. Although the charge type of the micelle has no effect on the RAE of neutral antioxidants, micelles of different charge types do have an effect on the RAE value of charged antioxidants such as ascorbic acid, other 2-hydroxytetronic acids, and Trolox C. In 0.10 M SDS micelles, ascorbic acid and alpha-tocopherol are shown to have an additive effect, not a synergistic effect, as antioxidants.

  DOI：

  10.1021/jo00065a013

文献信息

• A rapid screening test to determine the antioxidant potencies of natural and synthetic antioxidants
  作者：William A. Pryor、Joseph A. Cornicelli、Larry J. Devall、Bradley Tait、B. K. Trivedi、D. T. Witiak、Mingdan Wu

  DOI：10.1021/jo00065a013

  日期：1993.6

  This paper presents a simple and convenient method for measuring antioxidant efficiencies in a model system consisting of micelles of sodium dodecyl sulfate (SDS) with added linoleic acid. The analytical method involves following the development of absorption at 234 nm due to the conjugated diene hydroperoxide of linoleic acid; 2,2'-azobis(2-amidinopropane) dihydrochloride (ABAP) is used as the initiator. The antioxidant efficiency of an antioxidant is defined as AE = k(inh)/k(p), where k(inh) is the rate constant for reaction of the peroxyl radical from linoleic acid with the antioxidant (eq 7 in the text) and k(p) is the propagation rate constant for autoxidation of linoleic acid (eq 5). The relative antioxidant efficiency (RAE) is defined as the AE of the test compound divided by that for alpha-tocopherol; thus, RAE values are equal to k(inh)/k(inh,alpha-tocopherol). Since the absolute value of the rate constant for reaction of alpha-tocopherol with peroxyl radicals is known in micellar systems, the absolute value of k(inh) for a given antioxidant can be calculated if required. To establish the reliability of the method we report the AE of 17 synthetic and naturally occurring antioxidants and compare values obtained by this method to others in the literature. For neutral antioxidants, the same AE values are obtained in both negatively-charged micelles of SDS and positively-charged micelles of hexadecyl trimethylammonium bromide (HDTBr). The relative antioxidant efficiencies are reported for more than 40 synthetic compounds that are potential antioxidants or anti-inflammatory compounds; most of these compounds are tocopherol, ascorbate, or 2-hydroxytetronic acid analogues. Although the charge type of the micelle has no effect on the RAE of neutral antioxidants, micelles of different charge types do have an effect on the RAE value of charged antioxidants such as ascorbic acid, other 2-hydroxytetronic acids, and Trolox C. In 0.10 M SDS micelles, ascorbic acid and alpha-tocopherol are shown to have an additive effect, not a synergistic effect, as antioxidants.