4-acetoxy-9,10-cyclopropyl-3,15-dihydroxy-8-(3-methylbutyryloxy)-12-oxotrichothecene | 1128173-75-0

• 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: 4-acetoxy-9,10-cyclopropyl-3,15-dihydroxy-8-(3-methylbutyryloxy)-12-oxotrichothecene
• 英文别名: [(1S,2R,4S,5R,7S,8R,10R,11R,12S)-12-acetyloxy-2-(acetyloxymethyl)-11-hydroxy-1,5-dimethyl-13-oxo-9-oxatetracyclo[8.2.1.02,8.05,7]tridecan-4-yl] 3-methylbutanoate
• CAS: 1128173-75-0
• 化学式: C₂₄H₃₄O₉
• 分子量: 466.529
• InChiKey: MSAOPZXAYBZZAC-LEVDFBIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  T-2 toxin 在 a-无水葡萄糖酯 作用下， 反应 6.0h， 以9.8 mg的产率得到4,15-diacetoxy-10,12-cyclohexa-(10H)-3,9,12-trihydroxy-8-(3-methylbutyryloxy)trichothecene
  参考文献：
  名称：

  Structural Elucidation of T-2 Toxin Thermal Degradation Products and Investigations toward Their Occurrence in Retail Food

  摘要：

  The stability of T-2 toxin under the conditions of baking or cooking was investigated using heating experiments with the model substances alpha-D-glucose, alpha-D-methyl-glucopyranosid, N-alpha-acetyl-L-lysine methyl ester, and N-alpha-acetyl-cysteine methyl ester. The reaction residue was screened for degradation products using gas chromatography-mass spectrometry (GC-MS) and high-performance liquid chromatography with evaporative light-scattering detection (HPLC-ELSD). Although T-2 toxin was degraded under all conditions, only heating of T-2 toxin with a-D-glucose produced a mixture of three degradation products, which were isolated and identified by MS and nuclear magnetic resonance (NMR) experiments. The reaction mechanism for the formation of the T-2 degradation products was elucidated by quantum chemical calculations. The relevance of these degradation products was investigated by baking experiments as well as the analysis of retail food samples. In cell-culture studies using immortalized human kidney epithelial (IHKE) cells, the T-2 degradation products were less cytotoxic (formazan dye cytotoxicity assay) compared to T-2 toxin.

  DOI：

  10.1021/jf803516s