isocohumulone | 58501-77-2

• 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: isocohumulone
• 英文别名: trans-isocohumulone；(4R,5R)-3,4-dihydroxy-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)-2-(2-methylpropanoyl)cyclopent-2-en-1-one
• CAS: 58501-77-2
• 化学式: C₂₀H₂₈O₅
• 分子量: 348.439
• InChiKey: KKXFYHZSOIALRM-XOBRGWDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  cohumulone 在 acetate buffer 作用下， 以 乙醇 为溶剂， 生成 isocohumulone
  参考文献：
  名称：

  Isomerization and Degradation Kinetics of Hop (Humulus lupulus) Acids in a Model Wort-Boiling System

  摘要：

  The rate of isomerization of alpha acids to iso-alpha acids (the compounds contributing bitter taste to beer) was determined across a range of temperatures (90-130 degrees C) to characterize the rate at which iso-alpha acids are formed during kettle boiling. Multiple 12 mL stainless steel vessels were utilized to heat samples (alpha acids in a pH 5.2 buffered aqueous solution) at given temperatures, for varying lengths of time. Concentrations of alpha acids and iso-alpha acids were quantified by high-pressure liquid chromatography (HPLC). The isomerization reaction was found to be first order, with reaction rate varying as a function of temperature. Rate constants were experimentally determined to be k(1) = (7.9 x 10(11)) e((-1858/T)) for the isomerization reaction of alpha acids to iso-alpha acids, and k(2) = (4.1 x 10(12)) e((-12994/T)) for the subsequent loss of iso-alpha acids to uncharacterized degradation products. Activation energy was experimentally determined to be 98.6 kJ per mole for isomerization, and 108.0 U per mole for degradation. Losses of iso-alpha acids to degradation products were pronounced for cases in which boiling was continued beyond two half-lives of alpha-acid concentration.

  DOI：

  10.1021/jf0481296

文献信息

• METHOD FOR THE PURIFICATION OF SUBSTITUTED CYCLOPENT-2-EN-1-ONE CONGENERS AND SUBSTITUTED 1,3-CYCLOPENTADIONE CONGENERS FROM A COMPLEX MIXTURE USING COUNTERCURRENT SEPARATION
  申请人：Carroll Brian J.

  公开号：US20110257074A1

  公开（公告）日：2011-10-20

  Methods of purifying individual congeners of substituted cyclohexa-2,4-dienones, substituted cyclohexane-1,3,5-triones, substituted cyclopent-2-en-1-ones, and substituted 1,3-cyclopentadiones and compositions using the same are disclosed. The purification method includes the steps of: (a) selecting a congener to be isolated; (b) dissolving the mixture of congeners in a bi-phasic solvent system specific to the selected congener to be isolated, wherein said bi-phasic system has a partition coefficient from about 0.5 to 5.0; (c) subjecting the mixture dissolved in the bi-phasic solvent system to a counter current chromatography; and (d) isolating the selected congener in substantially pure form.
• Isomerization and Degradation Kinetics of Hop (<i>Humulus lupulus</i>) Acids in a Model Wort-Boiling System
  作者：Mark G. Malowicki、Thomas H. Shellhammer

  DOI：10.1021/jf0481296

  日期：2005.6.1

  The rate of isomerization of alpha acids to iso-alpha acids (the compounds contributing bitter taste to beer) was determined across a range of temperatures (90-130 degrees C) to characterize the rate at which iso-alpha acids are formed during kettle boiling. Multiple 12 mL stainless steel vessels were utilized to heat samples (alpha acids in a pH 5.2 buffered aqueous solution) at given temperatures, for varying lengths of time. Concentrations of alpha acids and iso-alpha acids were quantified by high-pressure liquid chromatography (HPLC). The isomerization reaction was found to be first order, with reaction rate varying as a function of temperature. Rate constants were experimentally determined to be k(1) = (7.9 x 10(11)) e((-1858/T)) for the isomerization reaction of alpha acids to iso-alpha acids, and k(2) = (4.1 x 10(12)) e((-12994/T)) for the subsequent loss of iso-alpha acids to uncharacterized degradation products. Activation energy was experimentally determined to be 98.6 kJ per mole for isomerization, and 108.0 U per mole for degradation. Losses of iso-alpha acids to degradation products were pronounced for cases in which boiling was continued beyond two half-lives of alpha-acid concentration.