3'-acetyldaidzein | 1254107-60-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 3'-acetyldaidzein
• CAS: 1254107-60-2
• 化学式: C₁₇H₁₂O₅
• 分子量: 296.279
• InChiKey: LUHCYVZKEUBZRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  87.74
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  视黄醛 、 3'-acetyldaidzein 在 potassium tert-butylate 作用下， 生成 3'(14'-apo-β-carotene-14'-carbonyl)daidzein
  参考文献：
  名称：

  Retinylisoflavonoid as a Novel Membrane Antioxidant

  摘要：

  We report a novel molecular dyad as an antioxidant, retinylisoflavonoid, with a retinal analogue C-22-aldehyde and the isoflavonoid daidzein covalently linked. Its physicochemical properties, pK(a) (pK(a1) = 8.45, pK(a2) = 11.42), oxidation potential (1.03 V vs NHE), and Log(10) partition (Log P = 1.96), as well as the Trolox equivalent antioxidant capacity (TEAC = 0.4), have been characterized. Spectroscopic and quantum chemical investigations have revealed the following unique structural characters: (i) Either free in solution or included in liposomal membranes, the C-22-aldehyde moiety of retinylisoflavonoid is coplanar with the B-ring of daidzein owing to the strong intramolecular hydrogen bonding C-14'=O center dot center dot center dot HO-B4'. Accordingly, the C-22-aldehyde moiety extends its pi-conjugation significantly to the B-ring. (ii) The inherent amphiphilicity of retinylisoflavonoid allows the C-22-aldehyde moiety embedded in the lipid phase of the liposomes, whereas the daidzein counterpart stays at the membrane surface, in effect facilitating interior-to-surface radical communication. As the result, the antilipooxidation activity of retinylisoflavonoid is improved significantly in protecting membrane lipids compared to the parent compounds alone or in combination, and importantly, the performance is more prominent under higher-level oxidative stress. This work provides an advanced case study of new antioxidant development based on optimized electronic and molecular structures.

  DOI：

  10.1021/jp106734p
• 作为产物：
  描述：

  大豆苷元二乙酯 在 aluminum (III) chloride 作用下， 生成 3'-acetyldaidzein
  参考文献：
  名称：

  Retinylisoflavonoid as a Novel Membrane Antioxidant

  摘要：

  We report a novel molecular dyad as an antioxidant, retinylisoflavonoid, with a retinal analogue C-22-aldehyde and the isoflavonoid daidzein covalently linked. Its physicochemical properties, pK(a) (pK(a1) = 8.45, pK(a2) = 11.42), oxidation potential (1.03 V vs NHE), and Log(10) partition (Log P = 1.96), as well as the Trolox equivalent antioxidant capacity (TEAC = 0.4), have been characterized. Spectroscopic and quantum chemical investigations have revealed the following unique structural characters: (i) Either free in solution or included in liposomal membranes, the C-22-aldehyde moiety of retinylisoflavonoid is coplanar with the B-ring of daidzein owing to the strong intramolecular hydrogen bonding C-14'=O center dot center dot center dot HO-B4'. Accordingly, the C-22-aldehyde moiety extends its pi-conjugation significantly to the B-ring. (ii) The inherent amphiphilicity of retinylisoflavonoid allows the C-22-aldehyde moiety embedded in the lipid phase of the liposomes, whereas the daidzein counterpart stays at the membrane surface, in effect facilitating interior-to-surface radical communication. As the result, the antilipooxidation activity of retinylisoflavonoid is improved significantly in protecting membrane lipids compared to the parent compounds alone or in combination, and importantly, the performance is more prominent under higher-level oxidative stress. This work provides an advanced case study of new antioxidant development based on optimized electronic and molecular structures.

  DOI：

  10.1021/jp106734p