(E)-6-Hydroxy-2,6-dimethyl-octa-2,7-dienoic acid (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester | 191548-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-6-Hydroxy-2,6-dimethyl-octa-2,7-dienoic acid (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester
• 英文别名: I(2)-D-Glucopyranose 1-[(2E)-6-hydroxy-2,6-dimethyl-2,7-octadienoate]；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2E)-6-hydroxy-2,6-dimethylocta-2,7-dienoate
• CAS: 191548-38-6
• 化学式: C₁₆H₂₆O₈
• 分子量: 346.378
• InChiKey: IVWJMPAYYVHQPT-HTOXQQIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (E)-6-Hydroxy-2,6-dimethyl-octa-2,7-dienoic acid (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester 在 吡啶 作用下， 生成 (E)-6-Hydroxy-2,6-dimethyl-octa-2,7-dienoic acid (2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester
  参考文献：
  名称：

  Isolation of Two Novel Terpenoid Glucose Esters from Riesling Wine

  摘要：

  A glycosidic isolate of Riesling wine was separated with multilayer coil countercurrent chromatography (MLCCC). After acetylation and subsequent purification by high-performance liquid chromatography (HPLC), the glucose esters of (E)-2,6-dimethyl-6-hydroxyocta-2,7-dienoic acid (1) and (2E,6E)-10,11-dihydroxy-3,7,11-trimethyl-2,6-dodecadienoic acid (2) were identified for the first time as nine constituents. The identification was achieved by mass spectrometry (DCI-MS) as well as nuclear magnetic resonance spectroscopy (H-1 NMR, C-13 NMR, COSY, HMBC). In biomimetic studies carried out with (E)-2,6-dimethyl-6-hydroxyocta-2,7-dienoic acid the potent nine aroma compound 3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (wine lactone) was formed, thus revealing an important aroma precursor function for glucoconjugate 1.

  DOI：

  10.1021/jf9706033