3,6,9-trihydroxymegastigma-4,7-diene | 97039-05-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,6,9-trihydroxymegastigma-4,7-diene
• 英文别名: 1-[(E)-3-hydroxybut-1-enyl]-2,6,6-trimethylcyclohex-2-ene-1,4-diol
• CAS: 97039-05-9
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: OHRIHSCUPPIXTD-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,6,9-trihydroxymegastigma-4,7-diene 在 水 作用下， 反应 0.5h， 以36%的产率得到3,4,9-trihydroxymegastigma-5,7-diene
  参考文献：
  名称：

  Generation of (E)-1-(2,3,6-Trimethylphenyl)buta-1,3-diene from C₁₃-Norisoprenoid Precursors

  摘要：

  Three C-13-norisoprenoid compounds, 3,6,9-trihydroxymegastigma-4,7-diene (6), 3,4,9-trihydroxymegastigma-5,7-diene (4), and the actiniclols (8), have all been synthesized and subjected to acid hydrolysis. All three were shown to generate (E)-1-(2,3,6-trimethylphenyl)buta-1,3-diene (1) under wine conservation conditions. At 45 degrees C, approximately 4000-5000 ng/L of 1 was formed from 1.0 mg/L of precursor, after 173 days, while at 25 degrees C more wine-like amounts (200-600 ng/L) were observed. A glucoside, 4,5-dihydrovomifoliol-C-9-beta-D-glucopyranoside (9b), was isolated from grapevine leaves by multilayer coil countercurrent chromatography (MLCCC), and its stereochemistry was deduced as being (5R, 6S, 9R) by NMR and CD spectroscopy. Hydrolysis of this glucoside produced 1, but in quantities insufficient to account for the levels observed in wine.

  DOI：

  10.1021/jf051039w
• 作为产物：
  描述：

  (3E,1'R*,4'S*)-4-(1',4'-Dihydroxy-2',6',6'-trimethyl-2'-cyclohexenyl)-3-buten-2-on 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以17%的产率得到3,6,9-trihydroxymegastigma-4,7-diene
  参考文献：
  名称：

  Generation of (E)-1-(2,3,6-Trimethylphenyl)buta-1,3-diene from C₁₃-Norisoprenoid Precursors

  摘要：

  Three C-13-norisoprenoid compounds, 3,6,9-trihydroxymegastigma-4,7-diene (6), 3,4,9-trihydroxymegastigma-5,7-diene (4), and the actiniclols (8), have all been synthesized and subjected to acid hydrolysis. All three were shown to generate (E)-1-(2,3,6-trimethylphenyl)buta-1,3-diene (1) under wine conservation conditions. At 45 degrees C, approximately 4000-5000 ng/L of 1 was formed from 1.0 mg/L of precursor, after 173 days, while at 25 degrees C more wine-like amounts (200-600 ng/L) were observed. A glucoside, 4,5-dihydrovomifoliol-C-9-beta-D-glucopyranoside (9b), was isolated from grapevine leaves by multilayer coil countercurrent chromatography (MLCCC), and its stereochemistry was deduced as being (5R, 6S, 9R) by NMR and CD spectroscopy. Hydrolysis of this glucoside produced 1, but in quantities insufficient to account for the levels observed in wine.

  DOI：

  10.1021/jf051039w

文献信息

• Free and bound 6,9-dihydroxymegastigm-7-en-3-one in Vitis vinifera grapes and wine
  作者：Mark A. Sefton、Peter Winterhalter、Patrick J. Williams

  DOI：10.1016/0031-9422(92)83154-q

  日期：1992.5

  4-Hydroxy-4-(3-hydroxy-1-butenyl)-3,3,5-trimethylcyclohexanone (6,9-dihydroxymegastigm-7-en-3-one) was synthesized from vomifoliol and was identified for the first time as a common constituent of Vitis vinifera grapes in both free and conjugated forms, as well as a minor constituent of French and American oakwood extracts. The corresponding beta-D-glucopyranoside was isolated from a Riesling wine.
• The actinidols: nor-isoprenoid compounds in grapes, wines and spirits
  作者：Eugene Dimitriadis、Christopher R. Strauss、Bevan Wilson、Patrick J. Williams

  DOI：10.1016/s0031-9422(00)84890-6

  日期：1985.1