Methyl 11-phenoxyundecanoate | 88444-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Methyl 11-phenoxyundecanoate
• CAS: 88444-13-7
• 化学式: C₁₈H₂₈O₃
• 分子量: 292.419
• InChiKey: WCFTVVSMRMEDSF-UHFFFAOYSA-N

物化性质

• 沸点：
  378.1±15.0 °C(Predicted)
• 密度：
  0.979±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 11-phenoxyundecanoate 、 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 [(2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2H-furan-2-yl]-2-hydroxyethyl] 11-phenoxyundecanoate
  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

• Pentanedioic acid derivatives
  申请人：G.D. Searle & Co.

  公开号：EP0089674A1

  公开（公告）日：1983-09-28

  Derivates of β-hydroxy-β-alkylglutaric acid are described which are useful to inhibit the formation of serum cholesterol by virtue of their ability to inhibit β-hydroxy-β-methylglutaryl-CoA(HMG CoA), the rate-controlling substance in the synthesis of serum cholesterol.

  本文描述了β-羟基-β-烷基戊二酸的衍生物，这些衍生物能够抑制血清胆固醇的形成，因为它们能够抑制血清胆固醇合成过程中的速率控制物质--β-羟基-β-甲基戊二酰-CoA（HMG CoA）。
• 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.