cis-humulinic acid | 24183-31-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基酸
• 英文名称: cis-humulinic acid
• CAS: 24183-31-1
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: PPIJHFDNRWNWJU-QMTHXVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  律草酮 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以78%的产率得到
  参考文献：
  名称：

  Oxidation of Isohumulones Induces the Formation of Carboxylic Acids by Hydrolytic Cleavage

  摘要：

  The degradation of isohumulones in mechanistic experiments was investigated. Incubation of trans-isohumulone in the presence of L-proline led to the formation of carboxylic acids and their corresponding proline amides. In the context of isohumulones unknown amides were verified first in model incubations and then in beer for the first time by comparison with authentic reference standards via LC-MS analyses. Carboxylic acids and amides were formed preferably under oxidative conditions and increasing pH. Stable isotope experiments excluded the incorporation of molecular oxygen into carboxylic acids, strongly indicating a hydrolytic mechanism via beta-dicarbonyl cleavage. The proposed mechanism includes oxidation and thereby incorporation of molecular oxygen to the isohumulone ring structure followed by hydrolytic cleavage leading to acids and amides.

  DOI：

  10.1021/jf501826h

文献信息

• COMPOSITIONS AND FOODS FOR IMPROVING LIPID METABOLISM
  申请人：KIRIN BEER KABUSHIKI KAISHA

  公开号：EP1481671B1

  公开（公告）日：2011-08-31
• Compositions and foods for improving lipid metabolism
  申请人：Yajima Hiroaki

  公开号：US20060233902A1

  公开（公告）日：2006-10-19

  It is intended to provide compositions and foods for use in the treatment, prophylaxis, or amelioration of diseases or symptoms which can be treated, prevented or ameliorated by activating PPAR, in particular, insulin resistant diabetes and hyperlipidemia. Namely, medicinal compositions usable in treating, preventing or improving diseases or symptoms which can be treated, prevented or ameliorated by activation PPAR which contain humulones, isohumulones or lupulones or pharmaceutically acceptable salts or solvates thereof.
• TASTE-MASKED DOSAGE FORMS
  申请人：MSB Holdings, Inc

  公开号：US20210346385A1

  公开（公告）日：2021-11-11

  Sublingual dosage forms comprising a bitter active ingredient (including sildenafil, tadalafil, tetrahydrocannabinol, and cannabidiol) and a bitterness reducing agent are described. Methods of treating sexual dysfunction by administering the sublingual dosage form to an individual in need thereof are also described.
• Oxidation of Isohumulones Induces the Formation of Carboxylic Acids by Hydrolytic Cleavage
  作者：Stefan Rakete、Robert Berger、Steffi Böhme、Marcus A. Glomb

  DOI：10.1021/jf501826h

  日期：2014.7.30

  The degradation of isohumulones in mechanistic experiments was investigated. Incubation of trans-isohumulone in the presence of L-proline led to the formation of carboxylic acids and their corresponding proline amides. In the context of isohumulones unknown amides were verified first in model incubations and then in beer for the first time by comparison with authentic reference standards via LC-MS analyses. Carboxylic acids and amides were formed preferably under oxidative conditions and increasing pH. Stable isotope experiments excluded the incorporation of molecular oxygen into carboxylic acids, strongly indicating a hydrolytic mechanism via beta-dicarbonyl cleavage. The proposed mechanism includes oxidation and thereby incorporation of molecular oxygen to the isohumulone ring structure followed by hydrolytic cleavage leading to acids and amides.