6-O-[(+)-L-ascorbic acid]-6'-O-[(-)-D-isoascorbic acid] dodecanedioate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-O-[(+)-L-ascorbic acid]-6'-O-[(-)-D-isoascorbic acid] dodecanedioate
• 英文别名: 1-O-[(2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2H-furan-2-yl]-2-hydroxyethyl] 12-O-[(2R)-2-[(2R)-3,4-dihydroxy-5-oxo-2H-furan-2-yl]-2-hydroxyethyl] dodecanedioate
• 化学式: C₂₄H₃₄O₁₄
• 分子量: 546.526
• InChiKey: JWKHXZXIDRXHAT-IETVQMFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  38
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  227
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  6-O-[(+)-L-ascorbic acid]-vinyl dodecanedioate 、 D-异抗坏血酸 在 immobilized lipase from Candida Antarctica 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以47%的产率得到6-O-[(+)-L-ascorbic acid]-6'-O-[(-)-D-isoascorbic acid] dodecanedioate
  参考文献：
  名称：

  Symmetric and Asymmetric Bolaamphiphiles from Ascorbic Acid

  摘要：

  The properties of novel bolaamphiphiles that carry epimers of vitamin C (L-ascorbic acid and/or D-isoascorbic acid) as hydrophilic head groups, and an interconnecting aliphatic C-12 chain (DD, DL, and LL) were investigated by differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), small-angle X-ray scattering (SAXS), X-ray diffraction (XRD), and Fourier transform infrared spectroscopy (FTIR) in the solid state (anhydrous powders) and in aqueous dispersions as a function of the surfactant concentration. Upon heating, the aqueous dispersions undergo a phase transition from a hydrated semicrystalline "coagel" to a micellar phase. The results suggest that the headgroup chirality determines the formation of either inter- or intramolecular hydrogen bonds between the polar heads, which affect the phase behavior and structural properties of the nanoassemblies produced by these surfactants in water dispersions. The DSC data of aqueous dispersions were analyzed to obtain the size distribution of the pores in the coagel state.

  DOI：

  10.1021/jp204920y

文献信息

• Symmetric and Asymmetric Bolaamphiphiles from Ascorbic Acid
  作者：Christian Dolle、Pietro Magrone、Sergio Riva、Moira Ambrosi、Emiliano Fratini、Niccolò Peruzzi、Pierandrea Lo Nostro

  DOI：10.1021/jp204920y

  日期：2011.10.13

  The properties of novel bolaamphiphiles that carry epimers of vitamin C (L-ascorbic acid and/or D-isoascorbic acid) as hydrophilic head groups, and an interconnecting aliphatic C-12 chain (DD, DL, and LL) were investigated by differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), small-angle X-ray scattering (SAXS), X-ray diffraction (XRD), and Fourier transform infrared spectroscopy (FTIR) in the solid state (anhydrous powders) and in aqueous dispersions as a function of the surfactant concentration. Upon heating, the aqueous dispersions undergo a phase transition from a hydrated semicrystalline "coagel" to a micellar phase. The results suggest that the headgroup chirality determines the formation of either inter- or intramolecular hydrogen bonds between the polar heads, which affect the phase behavior and structural properties of the nanoassemblies produced by these surfactants in water dispersions. The DSC data of aqueous dispersions were analyzed to obtain the size distribution of the pores in the coagel state.