(-)-artemisia alcohol | 29887-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-artemisia alcohol
• 英文别名: Artemisia Alcohol；artemisin alcohol；(4S)-3,3,6-trimethylhepta-1,5-dien-4-ol
• CAS: 29887-38-5
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: WPPVSYVQAKQNJK-VIFPVBQESA-N

物化性质

• LogP：
  2.872 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-artemisia alcohol 在 His-tagged Artemisia annua monoterpene alcohol dehydrogenase 2 、 β-烟酰胺腺嘌呤二核苷酸 作用下， 反应 0.5h， 生成 蒿酮
  参考文献：
  名称：

  A glandular trichome-specific monoterpene alcohol dehydrogenase from Artemisia annua

  摘要：

  The major components of the isoprenoid-rich essential oil of Artemisia annua L. accumulate in the subcuticular sac of glandular secretory trichomes. As part of an effort to understand isoprenoid biosynthesis in A. annua, an expressed sequence tag (EST) collection was investigated for evidence of genes encoding trichome-specific enzymes. This analysis established that a gene denoted Adh2, encodes an alcohol dehydrogenase and shows a high expression level in glandular trichomes relative to other tissues. The gene product, ADH2, has up to 61% amino acid identity to members of the short chain alcohol dehydrogenase/reductase (SDR) superfamily, including Forsythia x inter-media secoisolariciresinol dehydrogenase (49.8% identity). Through in vitro biochemical analysis, ADH2 was found to show a strong preference for monoterpenoid secondary alcohols including carveol, borneol and artemisia alcohol. These results indicate a role for ADH2 in monoterpenoid ketone biosynthesis in A. annua glandular trichomes. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2010.04.026
• 作为产物：
  描述：

  蒿酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 (-)-β-artemisia alcohol 、 (-)-artemisia alcohol
  参考文献：
  名称：

  A glandular trichome-specific monoterpene alcohol dehydrogenase from Artemisia annua

  摘要：

  The major components of the isoprenoid-rich essential oil of Artemisia annua L. accumulate in the subcuticular sac of glandular secretory trichomes. As part of an effort to understand isoprenoid biosynthesis in A. annua, an expressed sequence tag (EST) collection was investigated for evidence of genes encoding trichome-specific enzymes. This analysis established that a gene denoted Adh2, encodes an alcohol dehydrogenase and shows a high expression level in glandular trichomes relative to other tissues. The gene product, ADH2, has up to 61% amino acid identity to members of the short chain alcohol dehydrogenase/reductase (SDR) superfamily, including Forsythia x inter-media secoisolariciresinol dehydrogenase (49.8% identity). Through in vitro biochemical analysis, ADH2 was found to show a strong preference for monoterpenoid secondary alcohols including carveol, borneol and artemisia alcohol. These results indicate a role for ADH2 in monoterpenoid ketone biosynthesis in A. annua glandular trichomes. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2010.04.026

文献信息

• 3,3-Dimethylallyldiisopinocampheylborane: A novel reagent for chiral isoprenylation of aldehydes. Synthesis of (+)- and (−)-artemisia alcohol in exceptionally high enantiomeric purity
  作者：Herbert C. Brown、Prabhakar K. Jadhav

  DOI：10.1016/s0040-4039(01)80116-7

  日期：1984.1

  3,3-Dimethylallyldiisopinocampheylborane, on condensation with aldehydes, furnishes 3,3-dimethyl-l-alken-4-ols in 89–96% ee, including artemisia alcohol (96% ee) in both natural enantiomeric forms.

  3,3-二甲基烯丙基二硫代樟脑硼烷与醛缩合后，得到89,96％ee的3,3-二甲基-1-烯基-4-醇，包括两种天然对映体形式的蒿醇（96％ee）。
• Chiral synthesis via organoboranes. 6. Asymmetric allylboration via chiral allyldialkylboranes. Synthesis of homoallylic alcohols with exceptionally high enantiomeric excess
  作者：Prabhakar K. Jadhav、Krishna S. Bhat、P. Thirumalai Perumal、Herbert C. Brown

  DOI：10.1021/jo00354a003

  日期：1986.2
• JADHAV, P. K.;BHAT, K. S.;PERUMAL, P. T.;BROWN, H. C., J. ORG. CHEM., 1986, 51, N 4, 432-439
  作者：JADHAV, P. K.、BHAT, K. S.、PERUMAL, P. T.、BROWN, H. C.

  DOI：——

  日期：——
• A glandular trichome-specific monoterpene alcohol dehydrogenase from Artemisia annua
  作者：Devin R. Polichuk、Yansheng Zhang、Darwin W. Reed、Janice F. Schmidt、Patrick S. Covello

  DOI：10.1016/j.phytochem.2010.04.026

  日期：2010.8

  The major components of the isoprenoid-rich essential oil of Artemisia annua L. accumulate in the subcuticular sac of glandular secretory trichomes. As part of an effort to understand isoprenoid biosynthesis in A. annua, an expressed sequence tag (EST) collection was investigated for evidence of genes encoding trichome-specific enzymes. This analysis established that a gene denoted Adh2, encodes an alcohol dehydrogenase and shows a high expression level in glandular trichomes relative to other tissues. The gene product, ADH2, has up to 61% amino acid identity to members of the short chain alcohol dehydrogenase/reductase (SDR) superfamily, including Forsythia x inter-media secoisolariciresinol dehydrogenase (49.8% identity). Through in vitro biochemical analysis, ADH2 was found to show a strong preference for monoterpenoid secondary alcohols including carveol, borneol and artemisia alcohol. These results indicate a role for ADH2 in monoterpenoid ketone biosynthesis in A. annua glandular trichomes. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.