(2S,3R,4S,5R,6R)-6-(dodecoxymethyl)oxane-2,3,4,5-tetrol | 204906-95-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5R,6R)-6-(dodecoxymethyl)oxane-2,3,4,5-tetrol
• CAS: 204906-95-6
• 化学式: C₁₈H₃₆O₆
• 分子量: 348.48
• InChiKey: TVGHHSJVOULIEK-ICUGJSFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  alpha-D-半乳糖 在 硫酸 、 sodium hydride 、 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,3R,4S,5R,6R)-6-(dodecoxymethyl)oxane-2,3,4,5-tetrol
  参考文献：
  名称：

  Synthesis, surface tension properties and antibacterial activities of amphiphilic d -galactopyranose derivatives

  摘要：

  Several amphiphilic D-galactopyranose derivatives were synthesized in which the glycosidic moiety was separated from the hydrophobic alkyl chain (along 8 or 12 carbon atoms) by a spacer arm (butyl, butynyl or benzyl) in order to increase their surfactant properties and to obtain new antibacterial compounds. The surface tensions of the products were analyzed by Critical Micelle Concentration (CMC) and gamma(CMC) measurements and the antimicrobial activities were assayed against 10 bacterial species by Minimum Inhibitory Concentration (MIC) determination in liquid broth. The introduction of an aliphatic spacer arm increased the amphiphilic properties of the compounds and the CMC values were 40-500 times lower than their analogs without spacer arm. In the same manner, the spacer arms significantly increased the antibacterial power of the compounds. The products 4d and 4e exhibiting a C12 alkyl chain and an aliphatic spacer arm (butyl and butynyl) were the best surfactants (CMC = 0.023 and 0.032 mmol/L, respectively) and presented also the best antibacterial activities (MIC = 15.62 and 3.91 mu g/mL for Micrococcus luteus, respectively). But the antibacterial activity of the newly synthesized products seemed to depend more on the cell wall composition of the bacteria than only on the amphiphilic character of the compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.032

文献信息

• COMPOSITION ANTIBACTERIENNE CONTENANT UN MELANGE ISOMERIQUE DE MONOETHERS OU DE MONOACETALS D'ALKYLE DE MONOSACCHARIDES
  申请人：Tereos Starch & Sweeteners Belgium

  公开号：EP3233874A1

  公开（公告）日：2017-10-25
• COMPOSITION ANTIBACTÉRIENNE CONTENANT UN MONOÉTHER OU UN MONOACÉTAL D'ALKYLE DE DÉSOXYHEXOSE
  申请人：Tereos Starch & Sweeteners Belgium

  公开号：EP3389731B1

  公开（公告）日：2020-07-29
• [EN] ANTIBACTERIAL COMPOSITION CONTAINING AN ISOMER MIXTURE OF MONOSACCHARIDE ALKYL MONOACETALS OR MONOETHERS<br/>[FR] COMPOSITION ANTIBACTERIENNE CONTENANT UN MELANGE ISOMERIQUE DE MONOETHERS OU DE MONOACETALS D'ALKYLE DE MONOSACCHARIDES
  申请人：SYRAL BELGIUM NV

  公开号：WO2016098046A1

  公开（公告）日：2016-06-23

  La présente invention concerne une composition bactéricide ou bactériostatique comprenant un mélange d'isomères de monoéthers ou de monoacétals d'alkyle de monosaccharides, son utilisation dans le traitement ou la prévention des infections à bactéries Gram positif, son utilisation en tant que produit d'hygiène ou dermatologique à usage externe ainsi qu'une méthode de désinfection de surfaces.
• [EN] ANTIBACTERIAL COMPOSITION CONTAINING A DEOXYHEXOSE ALKYL MONOACETAL OR MONOETHER<br/>[FR] COMPOSITION ANTIBACTÉRIENNE CONTENANT UN MONOÉTHER OU UN MONOACÉTAL D'ALKYLE DE DÉSOXYHEXOSE
  申请人：TEREOS STARCH & SWEETENERS BELGIUM

  公开号：WO2017103904A1

  公开（公告）日：2017-06-22

  La présente invention concerne une composition bactéricide ou bactériostatique comprenant un éther ou un acétal d'alkyle de désoxyhexose ou le mélange d'isomères de celui-ci, son utilisation dans le traitement ou la prévention des infections à bactéries Gram positif, son utilisation en tant que produit d'hygiène ou dermatologique à usage externe ainsi qu'une méthode de désinfection de surfaces.
• Synthesis, surface tension properties and antibacterial activities of amphiphilic d -galactopyranose derivatives
  作者：Ludovic Chaveriat、Isabelle Gosselin、Cécile Machut、Patrick Martin

  DOI：10.1016/j.ejmech.2012.12.032

  日期：2013.4

  Several amphiphilic D-galactopyranose derivatives were synthesized in which the glycosidic moiety was separated from the hydrophobic alkyl chain (along 8 or 12 carbon atoms) by a spacer arm (butyl, butynyl or benzyl) in order to increase their surfactant properties and to obtain new antibacterial compounds. The surface tensions of the products were analyzed by Critical Micelle Concentration (CMC) and gamma(CMC) measurements and the antimicrobial activities were assayed against 10 bacterial species by Minimum Inhibitory Concentration (MIC) determination in liquid broth. The introduction of an aliphatic spacer arm increased the amphiphilic properties of the compounds and the CMC values were 40-500 times lower than their analogs without spacer arm. In the same manner, the spacer arms significantly increased the antibacterial power of the compounds. The products 4d and 4e exhibiting a C12 alkyl chain and an aliphatic spacer arm (butyl and butynyl) were the best surfactants (CMC = 0.023 and 0.032 mmol/L, respectively) and presented also the best antibacterial activities (MIC = 15.62 and 3.91 mu g/mL for Micrococcus luteus, respectively). But the antibacterial activity of the newly synthesized products seemed to depend more on the cell wall composition of the bacteria than only on the amphiphilic character of the compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.