5-isopropyl-2-methylphenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 1619941-85-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5-isopropyl-2-methylphenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• CAS: 1619941-85-3
• 化学式: C₂₀H₂₆O₆
• 分子量: 362.423
• InChiKey: DKMORUQIMRBLLL-SXLOBPIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-isopropyl-2-methylphenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 C₂₀H₂₈O₆
  参考文献：
  名称：

  Synthesis and antibacterial properties of 2,3-dideoxyglucosides of terpene alcohols and phenols

  摘要：

  Essential oils and their oxygenated terpene constituents possess potent antimicrobial properties. In the present study, a facile synthetic route to the 2,3-dideoxy 1-O-glucosides of important phenols and terpene alcohols in excellent yields (85-96%) has been delineated. Studies on their antimicrobial action against four food-borne pathogens--Bacillus cereus, Staphylococcus aureus, Escherichia coli and Yersinia enterocolitica--demonstrated that the zone of inhibition, in general, was higher for the 2,3-unsaturated 1-O-glucoside derivatives (1b-6b) and the corresponding saturated glucosides (1c-5c) when compared to the parent alcohols/phenols (1-6). The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values for these derivatives too were generally lower than those of the parent compounds. Furthermore, the time-kill and bacteriolysis assays too demonstrated the greater antimicrobial potential of the derivatives. The 2,3-dideoxy 1-O-glucosides of phenols and terpene alcohols were more effective in their antimicrobial action than the corresponding parent compounds. The study indicated that these novel derivatives can find useful application in control of food-related pathogenic microbes in foods.

  DOI：

  10.1016/j.foodchem.2015.03.078
• 作为产物：
  描述：

  香芹酚 、 乙酰化葡萄烯糖 在 zinc dibromide 作用下， 以 氯仿 为溶剂， 反应 0.42h， 以78.947%的产率得到
  参考文献：
  名称：

  ZnBr₂-Catalyzed and Microwave-Assisted Synthesis of 2,3-Unsaturated Glucosides of Hindered Phenols and Alcohols

  摘要：

  DOI：

  10.1080/00397911.2014.909490

文献信息

• 2,3-Dideoxyglucosides of selected terpene phenols and alcohols as potent antifungal compounds
  作者：D. James Bound、Pushpa S. Murthy、P. Srinivas

  DOI：10.1016/j.foodchem.2016.04.127

  日期：2016.11

  The antifungal activities of novel 2,3-unsaturated and 2,3-dideoxy 1-O-glucosides of carvacrol, thymol, and perillyl alcohol were tested against Aspergillus flavus, Aspergillus ochraceus, Fusarium oxysporum, Saccharomyces cerevisiae and Candida albicans. In the agar well diffusion tests, zones of inhibition for the derivatives of carvacrol, thymol and perillyl alcohol were higher (15–30 mm) in the

  的抗真菌活性的新型2,3-不饱和和2,3-二脱氧-1- ø香芹酚，百里酚，和紫苏子醇的-glucosides针对进行了测试黄曲霉，赭曲霉，尖镰孢，酿酒酵母和白色念珠菌。在琼脂孔扩散试验中，丝状真菌情况下香芹酚，百里香酚和紫苏醇衍生物的抑制区（15-30 mm）要比母体化合物的抑制区高。它们的MIC和MFC值表明2,3-不饱和和2,3-二脱氧1- O香芹酚和百里酚的β-葡糖苷比其他化合物表现出更多的杀真菌活性。此外，香芹酚和百里酚的2,3- dideoxyglucosides，表现出对antitoxigenic效果A.赭和黄曲霉和抑制生产赭曲霉毒素和黄曲霉毒素-B2的。碘化丙啶流入试验证明香芹酚及其2,3-不饱和的1- O-葡萄糖苷对白色念珠菌细胞的溶解以及膜完整性的损失。这些新的2，3-二脱氧葡萄糖苷可以用作食品中的抗真菌剂和调味品。