2-(2'(S),3'(R),4'-trihydroxybutyl)quinoxaline | 32781-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(2'(S),3'(R),4'-trihydroxybutyl)quinoxaline
• 英文别名: 3-DH quinoxaline；(2s,3r)-4-(Quinoxalin-2-yl)butane-1,2,3-triol；(2S,3R)-4-quinoxalin-2-ylbutane-1,2,3-triol
• CAS: 32781-22-9
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: KFKHJQAEESRVHL-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.5
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-deoxy-2-hexosulose 、 邻苯二胺 以 水 为溶剂， 反应 1.0h， 以0.34 mmol的产率得到2-(2'(S),3'(R),4'-trihydroxybutyl)quinoxaline
  参考文献：
  名称：

  Formation of α-Dicarbonyl Compounds in Beer during Storage of Pilsner

  摘要：

  With the aim of determining the formation of alpha-dicarbonyl intermediates during beer aging on the shelf, alpha-dicarbonyls were identified and quantified after derivatization with 1,2-diaminobenze to generate quinoxalines. The sensory effects of alpha-dicarbonyls were evaluated by the quantification of key Strecker aldehydes and by GC-olfactometry (GCO)analysis of beer headspace using solid phase microextraction. Four alpha-dicarbonyls, reported here for the first time, were detected in fresh and aged beers, three were derived from the 2,3-enolization pathway of mono- and disaccharides, and the fourth was derived from the epimerization of 3-deoxy-2-hexosulose. Ten alpha-dicarbonyls were quantified during beer processing and during different periods of beer aging at 28 degrees C. The aging periods were from 15 to 105 days. During beer aging, 1-deoxydiuloses were produced and degraded, while 1,4-dideoxydiuloses were produced at the highest rates. The GCO analysis indicated that forced beer aging increased the amounts of furaneol, trans-2-nonenal, and phenylacetaldehyde. The blockage of alpha-dicarbonyls inhibited the accumulation of sensory-active aldehydes in the beer headspace.

  DOI：

  10.1021/jf703696p

文献信息

• TAKAGI, MASANOSUKE;TSUCHIYA, KAZUO;KURIYAMA, MASAO;MIYANO, KEIICHI;MORITA+, DEHMPUN KAGAKU, 34,(1987) N, S. 203-210
  作者：TAKAGI, MASANOSUKE、TSUCHIYA, KAZUO、KURIYAMA, MASAO、MIYANO, KEIICHI、MORITA+

  DOI：——

  日期：——
• Formation of α-Dicarbonyl Compounds in Beer during Storage of Pilsner
  作者：Adriana Bravo、Julio C. Herrera、Erika Scherer、Yon Ju-Nam、Heinrich Rübsam、Jorge Madrid、Carsten Zufall、Rafael Rangel-Aldao

  DOI：10.1021/jf703696p

  日期：2008.6.1

  With the aim of determining the formation of alpha-dicarbonyl intermediates during beer aging on the shelf, alpha-dicarbonyls were identified and quantified after derivatization with 1,2-diaminobenze to generate quinoxalines. The sensory effects of alpha-dicarbonyls were evaluated by the quantification of key Strecker aldehydes and by GC-olfactometry (GCO)analysis of beer headspace using solid phase microextraction. Four alpha-dicarbonyls, reported here for the first time, were detected in fresh and aged beers, three were derived from the 2,3-enolization pathway of mono- and disaccharides, and the fourth was derived from the epimerization of 3-deoxy-2-hexosulose. Ten alpha-dicarbonyls were quantified during beer processing and during different periods of beer aging at 28 degrees C. The aging periods were from 15 to 105 days. During beer aging, 1-deoxydiuloses were produced and degraded, while 1,4-dideoxydiuloses were produced at the highest rates. The GCO analysis indicated that forced beer aging increased the amounts of furaneol, trans-2-nonenal, and phenylacetaldehyde. The blockage of alpha-dicarbonyls inhibited the accumulation of sensory-active aldehydes in the beer headspace.