(3aS,5aS,8aS)-3,3a-dihydroxy-6,6-dimethyl-2-(3-methylbutyryl)-5a,6,7,8-tetrahydro-3aH,5H-cyclopenta[c]pentalene-1,4-dione | 1611526-17-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,5aS,8aS)-3,3a-dihydroxy-6,6-dimethyl-2-(3-methylbutyryl)-5a,6,7,8-tetrahydro-3aH,5H-cyclopenta[c]pentalene-1,4-dione
• 英文别名: deisopropyltricycloiso-n-humulone；deisopropyltricycloisohumulone
• CAS: 1611526-17-0
• 化学式: C₁₈H₂₄O₅
• 分子量: 320.386
• InChiKey: QAWIDIVTAIKLCM-UZCIPKQKSA-N

物化性质

• 沸点：
  512.5±50.0 °C(predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为产物：
  描述：

  (6S)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one 以 正己烷 为溶剂， 反应 144.0h， 生成 (3aS,5aS,7S,8aS)-3,3a-dihydroxy-7-(1-hydroxy-1-methylethyl)-6,6-dimethyl-2-(3-methylbutyryl)-5a,6,7,8-tetrahydro-3aH,5H-cyclopenta[c]pentalene-1,4-dione 、 (3aS,5aS,7R,8aS)-3,3a-dihydroxy-7-(1-hydroxy-1-methylethyl)-6,6-dimethyl-2-(3-methylbutyryl)-5a,6,7,8-tetrahydro-3aH,5H-cyclopenta[c]-pentalene-1,4-dione 、 (3aS,5aS,7S,8aS)-3,3a-dihydroxy-7-(1-hydroperoxy-1-methylethyl)-6,6-dimethyl-2-(3-methylbutyryl)-5a,6,7,8-tetrahydro-3aH,5H-cyclopenta[c]pentalene-1,4-dione 、 (3aS,5aS,8aS)-3,3a-dihydroxy-6,6-dimethyl-2-(3-methylbutyryl)-5a,6,7,8-tetrahydro-3aH,5H-cyclopenta[c]pentalene-1,4-dione 、 hemiacetal of 7,8-dihydroxy-4,4-dimethyl-9-(3-methylbutyryl)-3β-(1-hydroperoxy-1-methylethyl)-5α-H-tricyclo[5.3.1.01,5]undec-8-ene-10,11-dione
  参考文献：
  名称：

  Structural Elucidation of Humulone Autoxidation Products and Analysis of Their Occurrence in Stored Hops

  摘要：

  The transformation of α-acids [in hops (Humulus lupulus L.)] to iso-α-acids (in beer) during the brewing process is well known, but the occurrence and structure of the oxidized α-acids during hop storage are not well documented. Because an understanding of these oxidized compounds is essential to optimize the effects of oxidized hops on the quality of beer, we investigated the autoxidation products of humulone (a representative congener of α-acids) using a simplified autoxidation model. Among the oxidation products, tricyclooxyisohumulones A (1) and B (2), tricycloperoxyisohumulone A (3), deisopropyltricycloisohumulone (4), and the hemiacetal 5 of tricycloperoxyhumulone A (5') were isolated, and their structures were elucidated for the first time. The occurrence of compounds 1-4 in stored hops was verified using LC/MS/MS analysis. We also monitored the levels of compounds 1-4 during hop storage using LC/MS/MS analysis.

  DOI：

  10.1021/np4008427