6''-O-lauroyl neohesperidin | 502764-74-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6''-O-lauroyl neohesperidin
• 英文别名: naringin 6''-O-laurate；[(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-[[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl dodecanoate
• CAS: 502764-74-1
• 化学式: C₃₉H₅₄O₁₅
• 分子量: 762.849
• InChiKey: DTCKIJCJWACHOI-UCRXDCPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  54
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  231
• 氢给体数：
  7
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  柚皮苷 、 月桂酸乙烯酯 在 Candida antarctica lipase B immobilized on acrylic resin 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以60%的产率得到6''-O-lauroyl neohesperidin
  参考文献：
  名称：

  Biocatalytic preparation of alkyl esters of citrus flavanone glucoside prunin in organic media

  摘要：

  The biocatalytic preparation of alkyl esters of prunin, a flavanone glucoside derivative of citric flavonoid naringin, was performed in organic media using two commercial immobilized lipases: Novozym 435 (Candida antarctica lipase B immobilized on an acrylic resin) and Lipozyme RM IM (Rhizomucor miehei lipase immobilized on an anion exchange resin). The influence of several reaction parameters on the performance and regioselectivity of the biocatalytic process was investigated using four solvents (acetone, acetonitrile, tetrahydrofurane and t-butanol) and vinyl laurate as a donor. The biocatalytic modification of prunin was strongly dependant on the solvent, the molar ratio of the substrates, the enzyme and the chain length of the donor. The acylation was highly regioselective, obtaining 6 ''-O-acyl monoesters except when the donor was vinyl acetate in which case a diester seemed to be formed. Novozym 435 proved to be a more efficient biocatalyst than Lipozyme RM IM. In acetone and acetonitrile, derivatives with a 100% conversion yield were synthesized after only 6 h of reaction at 50 degrees C. The modified derivatives preserved the antiradical activity of the flavanone glucoside and their solubility notably increased in the hydrophobic medium 1-octanol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.procbio.2010.07.022

文献信息

• Microfluidic reactor for lipase-catalyzed regioselective synthesis of neohesperidin ester derivatives and their antimicrobial activity research
  作者：Lihua Du、Zhipeng Jiang、Liangliang Xu、Nani Zhou、Jiahong Shen、Zhen Dong、Le Shen、Hong Wang、Xiping Luo

  DOI：10.1016/j.carres.2017.11.008

  日期：2018.1

  Lipase-catalyzed regioselective synthesis of neohesperidin ester derivatives was performed by Lipase TL IM from Thermomyces lanuginosus in a continuous-flow microreactor and then their antimicrobial activity was studied. It appears that neohesperidin, neohesperidin dihydrochalcone with primary OH on the sugar part is the most reactive substrate. Various reaction parameters were investigated including

  在连续流微反应器中，通过脂酶TL IM从羊毛嗜热菌中进行脂酶催化的新橙皮苷酯衍生物的区域选择性合成，然后研究其抗菌活性。似乎新橙皮苷，新橙皮苷二氢查耳酮在糖部分上具有伯羟基是最活泼的底物。研究了各种反应参数，包括底物摩尔比，反应时间和温度。在底物摩尔比为8：1（乙烯基酯：新橙皮苷）的最佳条件下，于52°C约35分钟获得最大转化率（92％）。然后，检查了改性的新橙皮苷酯衍生物的抗菌活性，并显示出对革兰氏阴性和革兰氏阳性细菌的极大改善。