vitamin C undecanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: vitamin C undecanoate
• 英文别名: vitamin C undecanoic acid ester；[(2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2H-furan-2-yl]-2-hydroxyethyl] undecanoate
• 化学式: C₁₇H₂₈O₇
• 分子量: 344.405
• InChiKey: ABDLOLPBDSNQHY-BLLLJJGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  维生素 C	ascorbic acid	50-81-7	C6H8O6	176.126

反应信息

• 作为产物：
  描述：

  十一酸甲酯 、 维生素 C 在 lipase acrylic resin from C_. antarctica (Novozyme 435(R)) 作用下， 以 2-甲基-2-丁醇 为溶剂， 60.0 ℃ 、20.0 kPa 条件下， 生成 vitamin C undecanoate
  参考文献：
  名称：

  Novel 6-O-acylated vitamin C derivatives as hyaluronidase inhibitors with selectivity for bacterial lyases

  摘要：

  Previously, we identified ascorbic acid 6-O-hexadecanoate as an up to 1500 times more potent inhibitor of bacterial and bovine hyaluronidases than the parent compound, vitamin C, and determined a crystal structure of hyaluronidase from Streptococcus pneumoniae in complex with the inhibitor. As the alkanoyl chain interacts with a hydrophobic patch of the enzyme we synthesized other 6-O-acylated vitamin C derivatives bearing various lipophilic residues and investigated the inhibition of Streptococcus agalactiae strain 4755 hyaluronidase (SagHyal(4755)) and of bovine testicular hyaluronidases (BTH) in a turbidimetric assay. All compounds showed selectivity for the bacterial enzyme. Whereas vitamin C 6-O-hexanoate only weakly inhibited SagHyal(4755), the inhibition of both enzymes increased with the length of the aliphatic chain. In the case of the 6-O-octadecanoate, IC50 values of 0.9 and 39 mu M for SagHyal(4755) and BTH, respectively, were determined. Partial replacement of the aliphatic chain with a phenyl, p-phenylene or p-biphenylyl group resulted in inhibitors with activity in the lower micromolar range, too. The title compounds are among the most potent inhibitors of both enzymes known to date. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.087

文献信息

• 一种维生素C高级脂肪酸酯的绿色合成方法
  申请人：上虞新和成生物化工有限公司

  公开号：CN112480046B

  公开（公告）日：2022-09-02

  本发明公开了一种维生素C高级脂肪酸酯的绿色合成方法，包括：在酰化反应催化剂催化下，维生素C与高级脂肪酸酐在无溶剂条件下发生酯化反应，经过后处理得到所述的维生素C高级脂肪酸酯。该合成方法对环境友好，反应温度较低，能耗小，成本低，原辅料的分子利用率较高，收率高。
• Coagels from alkanoyl–6-O-ascorbic acid derivatives as drug carriers: structure and rheology
  作者：Santiago Palma、Alvaro Jiménez-Kairuz、Laura Fratoni、Pierandrea Lo Nostro、Ruben Manzo、Daniel Allemandi

  DOI：10.1016/j.farmac.2003.07.010

  日期：2003.12

  6-O-Ascorbic acid alkanoates (ASCn, where n is the number of carbon atoms in the alkyl chain) behave as surfactants and form stable supramolecular assemblies in water, depending on chemical structure, concentration and temperature. In concentrated water dispersions, ASCn form liquid crystalline structures ('coagels'), below the critical micellar temperature (CMT), with a typical Krafft phenomenon. Such semisolid systems incorporate and stabilize drugs like anthralin, which is insoluble and unstable in aqueous media. The rheological behavior of coagels obtained from aqueous ASC8, ASC10, ASC11, ASC12, ASC14 and ASC16 was evaluated and related to the coagel structure. For ASC8, ASC12, ASC14 and ASC16 complex rheology was observed and spur values were determined. This behavior is indicative of a high three-dimensional structure. The spur value represents a sharp point of structural breakdown at low shear rate. At this point the semisolids acquire pseudoplastic flow with a very low viscosity. Instead, ASC10 and ASC11 coagels showed pseudoplastic flow and--in the case of ASC11--thixotropy was observed. The ASCn coagel rheological behavior and their capability to load pharmacologically active compounds point to a potentially valuable capacity for such systems as drug carriers.
• Novel 6-O-acylated vitamin C derivatives as hyaluronidase inhibitors with selectivity for bacterial lyases
  作者：Martin Spickenreither、Stephan Braun、Günther Bernhardt、Stefan Dove、Armin Buschauer

  DOI：10.1016/j.bmcl.2006.07.087

  日期：2006.10

  Previously, we identified ascorbic acid 6-O-hexadecanoate as an up to 1500 times more potent inhibitor of bacterial and bovine hyaluronidases than the parent compound, vitamin C, and determined a crystal structure of hyaluronidase from Streptococcus pneumoniae in complex with the inhibitor. As the alkanoyl chain interacts with a hydrophobic patch of the enzyme we synthesized other 6-O-acylated vitamin C derivatives bearing various lipophilic residues and investigated the inhibition of Streptococcus agalactiae strain 4755 hyaluronidase (SagHyal(4755)) and of bovine testicular hyaluronidases (BTH) in a turbidimetric assay. All compounds showed selectivity for the bacterial enzyme. Whereas vitamin C 6-O-hexanoate only weakly inhibited SagHyal(4755), the inhibition of both enzymes increased with the length of the aliphatic chain. In the case of the 6-O-octadecanoate, IC50 values of 0.9 and 39 mu M for SagHyal(4755) and BTH, respectively, were determined. Partial replacement of the aliphatic chain with a phenyl, p-phenylene or p-biphenylyl group resulted in inhibitors with activity in the lower micromolar range, too. The title compounds are among the most potent inhibitors of both enzymes known to date. (c) 2006 Elsevier Ltd. All rights reserved.