(2E,6E)-3,7-dimethyl-8-hydroxyoctadien-1-yl-β-D-glucopyranoside | 86589-34-6

• 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: (2E,6E)-3,7-dimethyl-8-hydroxyoctadien-1-yl-β-D-glucopyranoside
• 英文别名: 8-Hydroxygeraniol-1-O-α-D-glucoside；8-hydroxygeraniol β-D-glucopyranoside；8-hydroxygeranyl-β-D-glucoside；(2R,3R,4S,5S,6R)-2-[(2E,6E)-8-hydroxy-3,7-dimethylocta-2,6-dienoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 86589-34-6
• 化学式: C₁₆H₂₈O₇
• 分子量: 332.394
• InChiKey: XZHWSTJFHFQEOY-WIBXJVRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2E,6E)-3,7-dimethyl-8-hydroxyoctadien-1-yl-β-D-glucopyranoside 在 吡啶 作用下， 以2 mg的产率得到Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-((2E,6E)-8-acetoxy-3,7-dimethyl-octa-2,6-dienyloxy)-6-acetoxymethyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Isolation of a Glucosidic β-Damascenone Precursor from Rose Petals

  摘要：

  The 9-O-beta-D-glucopyranoside of 3-hydroxy-7,8-didehydro-beta-ionol (1) has been isolated from a glycosidic XAD-2 extract obtained from rose petals. In addition to the beta-damascenone-generating compound 1, the following glycoconjugates have been isolated and characterized as peracetates: 3-hydroxy-7,8-dihydro-beta-ionol 9-O-beta-D-glucopyranoside (2), 3-hydroxy-7,8-dihydro-beta-ionol 3-O-beta-D-glucopyranoside (3), 2-phenylethyl-O-beta-D-glucopyranoside (4), 2-phenylethyl-O-beta-D-galactopyranoside (5), benzyl-O-beta-D-glucopyranoside (6), (2E)-2,6-dimethyl-6-hydroxyocta-2,7-dienyl-O-beta-D-glucopyranoside (7), (2Z)-2,6-dimethyl-6-hydroxyocta-2, 7-dienyl-O-beta-D-glucopyranoside (8), and (2E,6E)-2,6-dimethyl-1-hydroxyocta-2,6-dien-8-yl-O-beta-D-glucopyranoside (9).

  DOI：

  10.1021/jf970278j
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((2E,6E)-8-hydroxy-3,7-dimethyl-octa-2,6-dienyloxy)-tetrahydro-pyran-4-yl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以12 mg的产率得到(2E,6E)-3,7-dimethyl-8-hydroxyoctadien-1-yl-β-D-glucopyranoside
  参考文献：
  名称：

  Isolation of 8-hydroxygeraniol-8-O-β-d-glucoside, a probable intermediate in biosynthesis of iridoid monoterpenes, from defensive secretions ofPlagiodera versicolora andGastrophysa viridula (Coleoptera: Chrysomelidae)

  摘要：

  8-Hydroxygeraniol and its 8-O-beta-D-glucoside have been found as trace components in the defensive secretions of Plagiodera versicolora and Gastrophysa viridula larvae. This discovery supports the hypothesis that the evolution of the utilization of plant precursors by some chrysomelid species was favored by the plesiomorphic occurrence of a beta-glucosidase and an oxidase in the defensive secretion of iridoid-producing species.

  DOI：

  10.1007/bf02066245

文献信息

• Isolation of a Glucosidic β-Damascenone Precursor from Rose Petals
  作者：Markus Straubinger、Holger Knapp、Noriaki Oka、Naoharu Watanabe、Peter Winterhalter

  DOI：10.1021/jf970278j

  日期：1997.10.1

  The 9-O-beta-D-glucopyranoside of 3-hydroxy-7,8-didehydro-beta-ionol (1) has been isolated from a glycosidic XAD-2 extract obtained from rose petals. In addition to the beta-damascenone-generating compound 1, the following glycoconjugates have been isolated and characterized as peracetates: 3-hydroxy-7,8-dihydro-beta-ionol 9-O-beta-D-glucopyranoside (2), 3-hydroxy-7,8-dihydro-beta-ionol 3-O-beta-D-glucopyranoside (3), 2-phenylethyl-O-beta-D-glucopyranoside (4), 2-phenylethyl-O-beta-D-galactopyranoside (5), benzyl-O-beta-D-glucopyranoside (6), (2E)-2,6-dimethyl-6-hydroxyocta-2,7-dienyl-O-beta-D-glucopyranoside (7), (2Z)-2,6-dimethyl-6-hydroxyocta-2, 7-dienyl-O-beta-D-glucopyranoside (8), and (2E,6E)-2,6-dimethyl-1-hydroxyocta-2,6-dien-8-yl-O-beta-D-glucopyranoside (9).
• Isolation of 8-hydroxygeraniol-8-O-β-d-glucoside, a probable intermediate in biosynthesis of iridoid monoterpenes, from defensive secretions ofPlagiodera versicolora andGastrophysa viridula (Coleoptera: Chrysomelidae)
  作者：D. Daloze、J. M. Pasteels

  DOI：10.1007/bf02066245

  日期：1994.8

  8-Hydroxygeraniol and its 8-O-beta-D-glucoside have been found as trace components in the defensive secretions of Plagiodera versicolora and Gastrophysa viridula larvae. This discovery supports the hypothesis that the evolution of the utilization of plant precursors by some chrysomelid species was favored by the plesiomorphic occurrence of a beta-glucosidase and an oxidase in the defensive secretion of iridoid-producing species.