(3R,7R)-1,3,7-octanetriol | 217650-11-8

• 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: (3R,7R)-1,3,7-octanetriol
• 英文别名: (3R,7R)-octane-1,3,7-triol
• CAS: 217650-11-8
• 化学式: C₈H₁₈O₃
• 分子量: 162.229
• InChiKey: NGACGNKKNNNNHK-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  乙酸酐 、 (3R,7R)-1,3,7-octanetriol 在 吡啶 作用下， 以95%的产率得到Acetic acid (1R,5R)-5-acetoxy-1-(2-acetoxy-ethyl)-hexyl ester
  参考文献：
  名称：

  Isolation, Identification, and Enantioselective Synthesis of Octane-1,3,7-triol:  Determination of Its Absolute Configuration

  摘要：

  Extracts obtained by solid-phase extraction from apples were separated by multilayer countercurrent chromatography. In the most polar fractions, the novel octane-1,3,7-triol was identified by H-1 and C-13 NMR as well as LC-MS and by comparison with the synthesized racemic reference compound. Resolution of the enantiomers was achieved after acetylation of the triol followed by GC separation. The enantioselective synthesis of the stereoisomers of octane-1,3,7-triol was performed using the building blocks (R)- and (R,S)-butane-1,3-diol and (S)- and (R,S)-butane-1,2,4-triol, Comparison with the isolated products indicated that the natural compound consisted of a mixture of (3R,7S)- and (SR,7R)-octane-1,3,7-triol in a ratio of 2:3. Since the C3 chiral center is enantiomerically pure, the triol might be biogenetically related to the known antimicrobial (R)-(+)-octane-1,3 -diol, the major volatile compound of some apple cultivars.

  DOI：

  10.1021/np980094e
• 作为产物：
  描述：

  (3R,7R)-1,7-Bis-benzyloxy-octan-3-ol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以95%的产率得到(3R,7R)-1,3,7-octanetriol
  参考文献：
  名称：

  Isolation, Identification, and Enantioselective Synthesis of Octane-1,3,7-triol:  Determination of Its Absolute Configuration

  摘要：

  Extracts obtained by solid-phase extraction from apples were separated by multilayer countercurrent chromatography. In the most polar fractions, the novel octane-1,3,7-triol was identified by H-1 and C-13 NMR as well as LC-MS and by comparison with the synthesized racemic reference compound. Resolution of the enantiomers was achieved after acetylation of the triol followed by GC separation. The enantioselective synthesis of the stereoisomers of octane-1,3,7-triol was performed using the building blocks (R)- and (R,S)-butane-1,3-diol and (S)- and (R,S)-butane-1,2,4-triol, Comparison with the isolated products indicated that the natural compound consisted of a mixture of (3R,7S)- and (SR,7R)-octane-1,3,7-triol in a ratio of 2:3. Since the C3 chiral center is enantiomerically pure, the triol might be biogenetically related to the known antimicrobial (R)-(+)-octane-1,3 -diol, the major volatile compound of some apple cultivars.

  DOI：

  10.1021/np980094e

文献信息

• ALDEHYDE DEHYDROGENASE VARIANTS AND METHODS OF USE
  申请人：Genomatica, Inc.

  公开号：EP3601546A1

  公开（公告）日：2020-02-05
• PROCESS AND SYSTEMS FOR OBTAINING 1,3-BUTANEDIOL FROM FERMENTATION BROTHS
  申请人：Genomatica, Inc.

  公开号：EP3600587A1

  公开（公告）日：2020-02-05
• 3-HYDROXYBUTYRYL-COA DEHYDROGENASE VARIANTS AND METHODS OF USE
  申请人：Genomatica, Inc.

  公开号：EP3601547A1

  公开（公告）日：2020-02-05
• ALDEHYDE DEHYDROGENASE VARIANTS AND METHODS OF USING SAME
  申请人：Genomatica, Inc.

  公开号：EP3856896A1

  公开（公告）日：2021-08-04
• [EN] PROCESS AND SYSTEMS FOR OBTAINING 1,3-BUTANEDIOL FROM FERMENTATION BROTHS<br/>[FR] PROCÉDÉS ET SYSTÈMES POUR OBTENIR DU 1,3-BUTANEDIOL À PARTIR DE BOUILLONS DE FERMENTATION
  申请人：GENOMATICA INC

  公开号：WO2018183628A1

  公开（公告）日：2018-10-04

  Provided herein are bioderived 1,3-butanediol compositions and systems and processes for producing such bioderived 1,3-butanediol compositions.