6-羟基-5,7-二甲氧基萘-2-羧酸 | 23204-42-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 6-羟基-5,7-二甲氧基萘-2-羧酸
• 英文名称: 6-hydroxy-5,7-dimethoxynaphthalene-2-carboxylic acid
• 英文别名: 6-hydroxy-5,7-dimethoxy-2-naphthoic acid；6-Hydroxy-5,7-dimethoxy-2-naphthoesaeure；2-Naphthalenecarboxylic acid, 6-hydroxy-5,7-dimethoxy-
• CAS: 23204-42-4
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: VVDSTIJVPBCANN-UHFFFAOYSA-N

物化性质

• 沸点：
  448.6±40.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-羟基-5,7-二甲氧基萘-2-羧酸 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 甲基5,6,7-三甲氧基-2-萘甲酸酯
  参考文献：
  名称：

  ELM木材的酚类成分：Ulmus thomasii的2-萘甲酸衍生物

  摘要：

  从榆树心材心材的水提取物中分离出两种新的2-萘甲酸衍生物。已经显示它们是6-羟基-5,7-二甲氧基-2-萘甲酸（I）和6-羟基-3-羟基甲基-5,7-二甲氧基-2-萘甲酸内酯（IV）。已经检查了几种相关的萘酚和萘甲酸及其衍生物的NMR光谱。萘酚衍生物的乙酰化在其NMR光谱中产生萘质子邻位至OH基团的特征性低场移位。

  DOI：

  10.1016/s0040-4020(01)82854-4
• 作为产物：
  描述：

  methyl 6-hydroxy-5,7-dimethoxy-2-naphthoate 在 sodium hydroxide 作用下， 反应 1.0h， 以96%的产率得到6-羟基-5,7-二甲氧基萘-2-羧酸
  参考文献：
  名称：

  Fuganti, Claudio; Serra, Stefano, Journal of Chemical Research, Miniprint, 1998, # 10, p. 2769 - 2782

  摘要：

  DOI：

文献信息

• Thomasidioic acid and 6-hydroxy-5,7-dimethoxy-2-naphthoic acid: Are they really natural products?
  作者：James L. Charlton、Kerri-Ann Lee

  DOI：10.1016/s0040-4039(97)01775-9

  日期：1997.10

  It has been shown that air oxidation of alkaline aqueous solutions of sinapic acid produces both thomasidioic acid (1), and 6-hydroxy-5,7-dimethoxy-2-naphthoic acid (2) in high yield, with the relative amounts dependent on the basicity of the solution. It has also been shown that naphthoic acid 2 is a secondary oxidation product of thomasidioic acid, a reaction that also produces 2,6-dimethoxy-p-benzoquione (3). The question of whether compounds 1, 2 and 3 are really natural products, as previously reported, is discussed. (C) 1997 Elsevier Science Ltd.
• Sinapate Dehydrodimers and Sinapate−Ferulate Heterodimers in Cereal Dietary Fiber
  作者：Mirko Bunzel、John Ralph、Hoon Kim、Fachuang Lu、Sally A. Ralph、Jane M. Marita、Ronald D. Hatfield、Hans Steinhart

  DOI：10.1021/jf020910v

  日期：2003.2.1

  Two 8-8-coupled sinapic acid dehydrodimers and at least three sinapate-ferulate heterodimers have been identified as saponification products from different insoluble and soluble cereal grain dietary fibers. The two 8-8-disinapates were authenticated by comparison of their GC retention times and mass spectra with authentic dehydrodimers synthesized from methyl or ethyl sinapate using two different single-electron metal oxidant systems. The highest amounts (481 mug/g) were found in wild rice insoluble dietary fiber. Model reactions showed that it is unlikely that the dehydrodisinapates detected are artifacts formed from free sinapic acid during the saponification procedure. The dehydrodisinapates presumably derive from radical coupling of sinapate-polymer esters in the cell wall; the radical coupling origin is further confirmed by finding 8-8 and 8-5 (and possibly 8-O-4) sinapate-ferulate cross-products. Sinapates therefore appear to have an analogous role to ferulates in cross-linking polysaccharides in cereal grains and presumably grass cell walls in general.
• Fuganti, Claudio; Serra, Stefano, Journal of Chemical Research, Miniprint, 1998, # 10, p. 2769 - 2782
  作者：Fuganti, Claudio、Serra, Stefano

  DOI：——

  日期：——
• Phenolic constituents of ELM wood
  作者：Chen-Loung Chen、F.D. Hostettler

  DOI：10.1016/s0040-4020(01)82854-4

  日期：1969.1

  Two new 2-naphthoic acid derivatives have been isolated from the aqueous extract of the heartwood of Ulmus thomasii Sarg. They have been shown to be 6-hydroxy-5,7-dimethoxy-2-naphthoic acid (I) and 6-hydroxy-3-hydroxymethyl-5,7-dimethoxy-2-naphthoic acid lactone (IV). The NMR spectra of several related naphthols and naphthoic acids and their derivatives have been examined. Acetylation of naphthol derivatives

  从榆树心材心材的水提取物中分离出两种新的2-萘甲酸衍生物。已经显示它们是6-羟基-5,7-二甲氧基-2-萘甲酸（I）和6-羟基-3-羟基甲基-5,7-二甲氧基-2-萘甲酸内酯（IV）。已经检查了几种相关的萘酚和萘甲酸及其衍生物的NMR光谱。萘酚衍生物的乙酰化在其NMR光谱中产生萘质子邻位至OH基团的特征性低场移位。