9-beta-羟基异绒白乳菇醛 | 96910-71-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 9-beta-羟基异绒白乳菇醛
• 英文名称: 9-hydroxyisovelleral
• 英文别名: 9-beta-Hydroxyisovelleral；(1aS,3aR,6aR,6bR)-3a-hydroxy-5,5,6b-trimethyl-1,4,6,6a-tetrahydrocyclopropa[e]indene-1a,2-dicarbaldehyde
• CAS: 96910-71-3
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: XJHRNHWYRIVNAL-NGFQHRJXSA-N

物化性质

• 沸点：
  366.4±42.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异绒白乳菇醛 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以7%的产率得到3-hydroxy-9,9,12-trimethylbicyclo<5.3.0>deca-1,3,6-triene-4-carbaldehyde
  参考文献：
  名称：

  Structure--Activity Relationships for Unsaturated Dialdehydes. 10. The Generation of Bioactive Products by Autoxidation of Isovelleral and Merulidial.

  摘要：

  The autoxidation of the two mutagenic and antimicrobial sesquiterpenes merulidial (1a) and isovelleral (5) generates a number of bioactive products that are suggested to be partly responsible for the mutagenic and antimicrobial activities of the two compounds. The biological activities of the autoxidation products are, as far as has been possible to assay, of the same order as the parent compounds, and it is shown that they are formed in normal bioassay media. Merulidial (1a) is especially interesting, as its rate of autoxidation is considerably higher compared with non-mutagenic derivatives of 1a. In addition, natural isovelleral [(+)-5] was found to be twice as mutagenic as synthetic isovelleral [(+/-)-5], indicating that (-)-isovelleral is only weakly active or inactive, and supporting the suggestion that the interaction of isovelleral (5) and its derivatives with DNA depends on the absolute stereochemistry of the unsaturated dialdehyde moiety.

  DOI：

  10.3891/acta.chem.scand.49-0530

文献信息

• Structure--Activity Relationships for Unsaturated Dialdehydes. 10. The Generation of Bioactive Products by Autoxidation of Isovelleral and Merulidial.
  作者：Mikael Jonassohn、Heidrun Anke、Paloma Morales、Olov Sterner、Inger Søtofte、Frode Mo、Tamas Bartfai、Ülo Langel

  DOI：10.3891/acta.chem.scand.49-0530

  日期：——

  The autoxidation of the two mutagenic and antimicrobial sesquiterpenes merulidial (1a) and isovelleral (5) generates a number of bioactive products that are suggested to be partly responsible for the mutagenic and antimicrobial activities of the two compounds. The biological activities of the autoxidation products are, as far as has been possible to assay, of the same order as the parent compounds, and it is shown that they are formed in normal bioassay media. Merulidial (1a) is especially interesting, as its rate of autoxidation is considerably higher compared with non-mutagenic derivatives of 1a. In addition, natural isovelleral [(+)-5] was found to be twice as mutagenic as synthetic isovelleral [(+/-)-5], indicating that (-)-isovelleral is only weakly active or inactive, and supporting the suggestion that the interaction of isovelleral (5) and its derivatives with DNA depends on the absolute stereochemistry of the unsaturated dialdehyde moiety.