5-(2-Hydroxy-heptadecyl)-benzene-1,3-diol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-(2-Hydroxy-heptadecyl)-benzene-1,3-diol
• 英文别名: 5-(2-Hydroxyheptadecyl)benzene-1,3-diol
• 化学式: C₂₃H₄₀O₃
• 分子量: 364.569
• InChiKey: SYXSPGMNIUYYGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  26
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(3,5-dimethoxyphenyl)-heptadecane-2-one 在 sodium tetrahydroborate 、 三溴化硼 作用下， 反应 72.0h， 生成 5-(2-Hydroxy-heptadecyl)-benzene-1,3-diol
  参考文献：
  名称：

  Cereal grain resorcinolic lipids: mono and dienoic homologues are present in rye grains

  摘要：

  Analyses (UV, IR, H-1-NMR, MS) of the main phenolic fractions isolated by sequential separation on normal-phase and by argentation chromatography on silica gel confirmed the presence of monoenoic and dienoic homologues of 1,3-dihydroxy-5-n-alkylbenzene in acetone extracts from rye grains. Conversion of mono and dienoic homologue dimethyl ethers to the cis-diols with osmium tetroxide, transformation of the diol to the acetonide with acetone and subsequent MS analysis of resulting derivatives showed that the breakdown pattern for the monoenoic homologues was consistent with a double bond in all the homologous chain length at the 8-position. For dienes, the results were not so conclusive, although the 8- and 11-positions appear to be the favoured ones. It has been also shown that rye 5-n-ketoalkylresorcinols contain a previously unobserved C17 homologue. All identifications were confirmed by comparison with synthetically obtained C19:0 and C21:0 5-n-alkylresorcinols and a 5-n-(2-keto-heptadecyl)resorcinol. Other minor phenolic components present in the acetone extract were identified as homologous 5-n-(2-hydroxyalkyl)resorcinols.

  DOI：

  10.1016/0009-3084(95)02480-7

文献信息

• Cereal grain resorcinolic lipids: mono and dienoic homologues are present in rye grains
  作者：Arkadiusz Kozubek、John H.P Tyman

  DOI：10.1016/0009-3084(95)02480-7

  日期：1995.10

  Analyses (UV, IR, H-1-NMR, MS) of the main phenolic fractions isolated by sequential separation on normal-phase and by argentation chromatography on silica gel confirmed the presence of monoenoic and dienoic homologues of 1,3-dihydroxy-5-n-alkylbenzene in acetone extracts from rye grains. Conversion of mono and dienoic homologue dimethyl ethers to the cis-diols with osmium tetroxide, transformation of the diol to the acetonide with acetone and subsequent MS analysis of resulting derivatives showed that the breakdown pattern for the monoenoic homologues was consistent with a double bond in all the homologous chain length at the 8-position. For dienes, the results were not so conclusive, although the 8- and 11-positions appear to be the favoured ones. It has been also shown that rye 5-n-ketoalkylresorcinols contain a previously unobserved C17 homologue. All identifications were confirmed by comparison with synthetically obtained C19:0 and C21:0 5-n-alkylresorcinols and a 5-n-(2-keto-heptadecyl)resorcinol. Other minor phenolic components present in the acetone extract were identified as homologous 5-n-(2-hydroxyalkyl)resorcinols.