6-O-caproyl L-ascorbate

• 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: 6-O-caproyl L-ascorbate
• 英文别名: vitamin C capraate；(S)-2-((R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl decanoate；6-O-Decanoyl-L-ascorbic acid；[(2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2H-furan-2-yl]-2-hydroxyethyl] decanoate
• 化学式: C₁₆H₂₆O₇
• 分子量: 330.378
• InChiKey: NXNYZMCJEATBKA-XHDPSFHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  正癸酸 在 氯化亚砜 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 1.5h， 生成 6-O-caproyl L-ascorbate
  参考文献：
  名称：

  L-ascorbyl 6-palmitate as lead compound targeting SphK1: an in silico and in vitro investigation

  摘要：

  鞘氨醇激酶（SphKs）是一类脂质激酶，在肿瘤中作为重要的限速酶受到广泛关注。抑制SphK1的活性可以导致抗癌效果。在这里，我们描述了通过计算机辅助药物设计发现的一种新的SphK1抑制剂——抗坏血酸棕榈酸酯的发现过程和生物特性。生化实验表明，抗坏血酸棕榈酸酯对SphK1具有强烈的抑制作用，IC50值为6.4μM。MTT实验显示，抗坏血酸棕榈酸酯对U87、A549、22RV1和A375细胞系具有抗癌作用。其中，抗坏血酸棕榈酸酯对22RV1细胞系具有显著的抑制活性，IC50值为41.57μM。为了探索结构活性关系，合成了四种抗坏血酸棕榈酸酯衍生物，并对其激酶活性进行了测试。抗坏血酸棕榈酸酯对SphK1的显著效果及其已知的无毒性表明，抗坏血酸棕榈酸酯可能是开发有效的SphK1抗癌抑制剂的首要化合物。

  DOI：

  10.1177/17475198211001819

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。
• Vegetable oil based dielectric coolant
  申请人：Cooper Industries, Inc.

  公开号：EP1304704A2

  公开（公告）日：2003-04-23

  A transformer includes a tank housing and a transformer core/coil assembly. The core/coil assembly is surrounded by a dielectric insulating fluid comprising a vegetable oil and an antioxidant.

  变压器包括一个油箱外壳和一个变压器铁芯/线圈组件。铁芯/线圈组件周围是由植物油和抗氧化剂组成的介电绝缘流体。
• 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.
• Continuous production of acyl l-ascorbates using a packed-bed reactor with immobilized lipase
  作者：Ko Kuwabara、Yoshiyuki Watanabe、Shuji Adachi、Kazuhiro Nakanishi、Ryuichi Matsuno

  DOI：10.1007/s11746-003-0791-0

  日期：2003.9

  AbstractSaturated acyl (6‐O‐caproyl, lauroyl, and myristoyl) and unsaturated acyl (6‐O‐oleoyl, linoleoyl, and arachidonoyl) l‐ascorbates were continuously synthesized at 50°C using a system where a column packed with ascorbic acid powder and a packed‐bed reactor with an immobilized lipase from Candida antarctica were connected in series. A productivity of 1.6–1.9 kg/L reactor·d was achieved for at least 11 d. The surface tension of the caproyl or lauroyl l‐ascorbate in aqueous solution was measured at various temperatures and pH to estimate the critical micelle concentration (CMC) of the acyl l‐ascorbate. The CMC values were independent of temperature but dependent on the pH. The value of the caproyl ascorbate increased with an increase in pH.
• 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.