6-O-[(+)-L-ascorbic acid]-6'-O-[(+)-L-ascorbic 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-[(+)-L-ascorbic acid] dodecanedioate
• 英文别名: 1,12-diascorbyl dodecanedioate；1,12-di-L-ascorbyl dodecanedioate；bis[(2S)-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-HCIHMXRSSA-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：

  十二烷二酸 、 维生素 C 在 硫酸 作用下， 反应 18.0h， 以46.4%的产率得到6-O-[(+)-L-ascorbic acid]-6'-O-[(+)-L-ascorbic acid] dodecanedioate
  参考文献：
  名称：

  Nanotubes from a Vitamin C-Based Bolaamphiphile

  摘要：

  A bolaform surfactant, 1,12-diascorbyl dodecanedioate (BOLA12), with ascorbic acid units as the polar headgroups was synthesized for the first time. Once dispersed in water above 0.5% w/w, BOLA12 forms hollow nanotubes as revealed by cryo-TEM experiments. These nanostructures transform into clear micellar solutions on heating. X-ray diffraction and SAXS experiments were performed both on the pure solid and on its aqueous dispersions. The critical aggregation concentration and the phase behavior were determined by conductivity and DSC experiments. The latter technique provided also the amount of strongly bound, solvating water molecules that surround the polar headgroups. BOLA12 shows the same reducing properties of ascorbic acid, as indicated by the antioxidant activity evaluated with the DPPH method. This feature was used for the reduction of Pd(II) ions on the surface of the nanoassemblies, which lead to the formation of large bundles homogeneously coated with palladium as observed in SEM micrographs.

  DOI：

  10.1021/ja057730x

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.
• Nanotubes from a Vitamin C-Based Bolaamphiphile
  作者：Moira Ambrosi、Emiliano Fratini、Viveka Alfredsson、Barry W. Ninham、Rodorico Giorgi、Pierandrea Lo Nostro、Piero Baglioni

  DOI：10.1021/ja057730x

  日期：2006.6.1

  A bolaform surfactant, 1,12-diascorbyl dodecanedioate (BOLA12), with ascorbic acid units as the polar headgroups was synthesized for the first time. Once dispersed in water above 0.5% w/w, BOLA12 forms hollow nanotubes as revealed by cryo-TEM experiments. These nanostructures transform into clear micellar solutions on heating. X-ray diffraction and SAXS experiments were performed both on the pure solid and on its aqueous dispersions. The critical aggregation concentration and the phase behavior were determined by conductivity and DSC experiments. The latter technique provided also the amount of strongly bound, solvating water molecules that surround the polar headgroups. BOLA12 shows the same reducing properties of ascorbic acid, as indicated by the antioxidant activity evaluated with the DPPH method. This feature was used for the reduction of Pd(II) ions on the surface of the nanoassemblies, which lead to the formation of large bundles homogeneously coated with palladium as observed in SEM micrographs.