berberine palmitate | 1271739-52-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: berberine palmitate
• 英文别名: 9,10-dimethoxy-2,3-methylenedioxy-5,6-dihydrodibenzo[a,g]quinolizinium palmitate
• CAS: 1271739-52-6
• 化学式: C₁₆H₃₁O₂*C₂₀H₁₈NO₄
• 分子量: 591.788
• InChiKey: LFBUNNWMNQOJGP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  7.31
• 重原子数：
  43.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  80.93
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  sodium palmitate 、 盐酸小檗碱 以 水 为溶剂， 以82%的产率得到berberine palmitate
  参考文献：
  名称：

  Fluorescent organic ion pairs based on berberine: counter-ion effect on the formation of particles and on the uptake by colon cancer cells

  摘要：

  反离子调节细胞中小檗碱离子对的荧光，这个过程可能与纳米粒子的形成有关。

  DOI：

  10.1039/c4ra09993a

文献信息

• Spontaneous Formation of Fluorescent Nanofibers and Reticulated Solid from Berberine Palmitate: A New Example of Aggregation-Induced Emission Enhancement in Organic Ion Pairs
  作者：Joe Chahine、Nathalie Saffon、Martine Cantuel、Suzanne Fery-Forgues

  DOI：10.1021/la104302d

  日期：2011.3.15

  The salt formed between the large aromatic berberine cation and the long-chain palmitate anion was synthesized and used to prepare aqueous suspensions of particles owing to a solvent exchange method. Under these conditions, elongated particles were readily obtained. They were studied by transmission microscopy with polarized light, as well as by fluorescence and electron microscopy. They were shown to be probably crystallized nanofibers, which were stable in suspension. Unexpectedly, upon filtration and drying, these fibers evolved to give a reticulated solid. The fluorescence properties of the compound were analyzed in solution, in aqueous suspension and in the powder crystalline state. Interestingly, berberine palmitate is virtually not fluorescent in aqueous solution because of the quenching effect of water, but transition to the solid state was accompanied by a strong increase in fluorescence intensity. This phenomenon was explained by the original molecular arrangement in the solid state. Actually, in the crystal, the anions form a distinct layer, which limits parallel-stacking of the fluorescent cations. Moreover, the berberine cations are protected from the access of water molecules, and so no quenching effect can take place. This example confirms that the newly introduced concept of ion-pair aggregation-induced fluorescence enhancement can be extended to a variety of structures. It also shows the interest of ion pairs for preparing fluorescent nanofibers and reticulated solids using a solvent-exchange method that is particularly easy to implement.