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生物质化学工程

生物质化学工程 ›› 2009, Vol. 43 ›› Issue (2): 1-5.

• 论文 •    下一篇

没食子酸萜醇酯的合成与结构鉴定研究

薄采颖1, 毕良武1, 赵振东1, 李冬梅1,2, 古研1,2, 王婧1,2, 张秋格1, 王玉民1, 周永红2   

  1. 1. 中国林业科学研究院林产化学工业研究所;生物质化学利用国家工程实验室;国家林业局林产化学工程重点开放性实验室, 江苏, 南京, 210042;2. 江苏强林生物能源有限公司, 江苏, 溧阳, 213364
  • 收稿日期:2009-01-05 修回日期:1900-01-01 出版日期:2009-03-30 发布日期:2009-03-30
  • 通讯作者: 毕良武,研究员,博士,从事天然产物化学与利用研究.E-mail:biliangwu@126.com

Study on Synthesis and Structure Identification of Terpenyl Gallates

BO Cai-ying1, BI Liang-wu1, ZHAO Zhen-dong1, LI Dong-mei1,2, GU Yan1,2, WANG Jing1,2, ZHANG Qiu-ge1, WANG Yu-min1, ZHOU Yong-hong2   

  1. 1. Institute of Chemical Industry of Forest Products, CAF;National Engineering Lab. for Biomass Chemical Utilization;Key and Open Lab. on Forest Chemical Engineering, SFA, Nanjing 210042, China;2. Jiangsu Qianglin Biomass Energy Co. Ltd., Liyang 213364, China
  • Received:2009-01-05 Revised:1900-01-01 Online:2009-03-30 Published:2009-03-30

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摘要： 提出一种没食子酸萜醇酯的舍成路线:先将没食子酸进行乙酰化保护得到3,4,-三乙酰没食子酸,3,4,-三乙酰没食子酸分别与金合欢醇、香叶醇、芳樟醇、橙花叔醇、薄荷醇和氢化松香醇等6种萜醇类化合物进行室温超声波辅助的N,N,-二环己基碳二亚胺脱水酯化,得到3,4,-三乙酰没食子酸萜醇酯;3,4,-三乙酰没食子酸萜醇酯再经水合肼脱乙酰化,得到对应的没食子酸萜醇酯.没食子酸金合欢酯、没食子酸香叶酯、没食子酸芳樟酯、没食子酸橙花叔醇酯、没食子酸薄荷酯和没食子酸氢化松香酯的总得率分别为86.17%、8.26%、76.32%、87.0%、79.22%和82.4%.该方法反应温度低,反应时间短,转化率较高.并对上述6种没食子酸萜醇酯的结构进行了鉴定.

关键词: 没食子酸萜醇酯, 乙酰化, 合成, 结构鉴定

Abstract: A synthetic route of terpenyl gallates was advanced. Gallic acid was acetylated to form 3,4,5-triacetoxybenzoic acid at first, 3,4,5-triacetoxybenzoic acid was esterified with six terpenyl alcohols such as farnesol, geraniol, linalool, nerolidol, menthol, and hydroabietyl alcohol by N,N'-dicyclohexyl carbodiimide (DCC) with the assistance of ultrasound at room temperature to produce terpenyl 3,4,5-triacetoxybenzates, respectively. The terpenyl 3,4,5-triacetoxybenzates were then deacetylated by hydrazine hydrate to produce corresponding terpenyl gallates. The total yield of farnesyl gallate, geranyl gallate, linalyl gallate, nerolidyl gallate, menthyl gallate, and hydroabietyl gallate were 86.17%, 85.26%, 76.32%, 87.50%, 79.22% and 82.54%, respectively. The synthetic method had advantages of low reaction temperature, short reaction time, and high conversion rate. The chemical structures of above six terpenyl gallates were identified at last.

Key words: terpenyl gallates, acetylation, synthesis, structural identification

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