carneic acid B methyl ester | 910046-28-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: carneic acid B methyl ester
• 英文别名: 5-[5R-hydroxy-2S-(3-hydroxy-1-methylpropenyl)-3,8-dimethyl-1R,2S,4aR,5,6,7,8R,8aR-octahydronaphthalen-1-yl]penta-2E,4E-dienoic acid methyl ester；methyl (2E,4E)-5-[(1R,2R,4aS,5R,8R,8aR)-5-hydroxy-2-[(E)-4-hydroxybut-2-en-2-yl]-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]penta-2,4-dienoate
• CAS: 910046-28-5
• 化学式: C₂₂H₃₂O₄
• 分子量: 360.494
• InChiKey: BIXRBOHCIZTJQQ-MIAGRYQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  carneic acid B methyl ester 、 4-硝基苯甲酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以15.6 mg的产率得到carneic acid B methyl ester dinitrobenzoate
  参考文献：
  名称：

  Carneic Acids A and B, Chemotaxonomically Significant Antimicrobial Agents from the Xylariaceous Ascomycete Hypoxylon carneum

  摘要：

  Carneic acids A and B ( 1, 2) are polyketide antibiotics structurally related to phomopsidin. They were isolated as major constituents of the stromata of Hypoxylon carneum, a species that had shown a highly specific secondary metabolite profile in a survey of xylariaceous ascomycetes based on HPLC profiling. Their chemical structures were elucidated by a combination of spectroscopic methods and by preparation of derivatives. An X-ray crystal structure of the dinitrobenzoate of carneic acid B methyl ester ( 8) was obtained, even allowing for determination of its absolute structure. The carneic acids showed weak antibacterial and moderate antifungal activities in the serial dilution assay against selected microbial organisms. They appear to be species-specific marker molecules in H. carneum from different geographic regions, but do not constitute major metabolites of more than 100 species of Xylariaceae. Their biological and chemotaxonomic significance is discussed.

  DOI：

  10.1021/np0602057
• 作为产物：
  描述：

  Carneic acid B 、 三甲基硅烷化重氮甲烷 以 甲醇 为溶剂， 反应 3.0h， 以13.3 mg的产率得到carneic acid B methyl ester
  参考文献：
  名称：

  Carneic Acids A and B, Chemotaxonomically Significant Antimicrobial Agents from the Xylariaceous Ascomycete Hypoxylon carneum

  摘要：

  Carneic acids A and B ( 1, 2) are polyketide antibiotics structurally related to phomopsidin. They were isolated as major constituents of the stromata of Hypoxylon carneum, a species that had shown a highly specific secondary metabolite profile in a survey of xylariaceous ascomycetes based on HPLC profiling. Their chemical structures were elucidated by a combination of spectroscopic methods and by preparation of derivatives. An X-ray crystal structure of the dinitrobenzoate of carneic acid B methyl ester ( 8) was obtained, even allowing for determination of its absolute structure. The carneic acids showed weak antibacterial and moderate antifungal activities in the serial dilution assay against selected microbial organisms. They appear to be species-specific marker molecules in H. carneum from different geographic regions, but do not constitute major metabolites of more than 100 species of Xylariaceae. Their biological and chemotaxonomic significance is discussed.

  DOI：

  10.1021/np0602057