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林产化学与工业

林产化学与工业 ›› 2009, Vol. 29 ›› Issue (3): 13-17.

• 研究报告 • 上一篇    下一篇

新铃兰醛VC缩醛的合成及其抗氧化性能的研究

王玉民1,2, 赵振东1, 毕良武1, 李冬梅1, 王婧1, 古研1, 薄采颖1   

  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. 泰山医学院 化学与化学工程学院, 山东 泰安 271016
  • 收稿日期:2009-03-26 修回日期:1900-01-01 出版日期:2009-06-30 发布日期:2009-06-30
  • 通讯作者: 赵振东(1960- ),男(白族),云南昌宁人,研究员,博士,博士生导师,主要从事天然产物及萜类化学利用、松树病虫害化学、应用化学等方面的研究工作;E-mail:zdzhao@publica1.ptt.js.cn。

Synthesis of VC Lyral Acetal and Its Antioxidation Activity

WANG Yu-min1,2, ZHAO Zhen-dong1, BI Liang-wu1, LI Dong-mei1, WANG Jing1, GU Yan1, BO Cai-ying1   

  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. School of Chemistry and Chemical Engineering, Taishan Medical College, Tai'an 271016, China
  • Received:2009-03-26 Revised:1900-01-01 Online:2009-06-30 Published:2009-06-30

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摘要： 以对甲苯磺酸为催化剂, N,N-二甲基甲酰胺(DMF)为溶剂,正己烷为带水剂,由新铃兰醛与VC(抗坏血酸)反应合成了新铃兰醛VC缩醛,产物含有约 74% 的A异构体和 26% 的B异构体,其主要化学结构经液相色谱-质谱(LC-MS)、FT-IR、1HNMR 鉴定。主要反应条件为:新铃兰醛与VC物质的量之比1:1.5,催化剂用量为新铃兰醛质量分数的 5%,搅拌回流反应时间 6h。用二苯代苦酰肼自由基(DPPH·)清除法测定了产物的抗氧化能力,结果表明,新铃兰醛VC缩醛清除DPPH·的能力(抗氧化能力)与VC相当,都明显强于常用的抗氧化剂BHT,有望成为油溶性良好的潜香型VC类抗氧化剂。

关键词: 新铃兰醛, VC(L-抗坏血酸), 新铃兰醛VC缩醛, 二苯代苦酰肼自由基

Abstract: VC lyral acetal (L-ascorbyl lyral acetal) was synthesized with VC (L-ascorbic acid) and lyral resolved in solvents N,N-dimethylformamide (DMF) andhexane as a water-carrying agent catalyzed by p-toluenesulfonic acid. VC lyral acetal, constituted of two isomers (A and B) in a ratio about 74% to 26%, was identified by its LC-MS, FT-IR and 1H NMR spectral data. The main reaction conditions are as follows:molar ratio 1 to 1.5 for lyral to VC, 5% of catalyst to mass of lyral, and stirring and refluxing for 6h. The antioxidation activity of VC lyral acetal was characterized by DPPH· (2,2-diphenyl-1-(2,4,6-tri-nitrophenyl)hydrazyl free radical) assay. The result shown that the ability of VC lyral acetal for scavenging DPPH· free radical (antioxidation activity) was similar with that of VC, but remarkably stronger than that of BHT, a common antioxidant, so the acetal would be applicable as agood oil-soluble VC-type antioxidant with latent aroma.

Key words: lyral, VC(L-ascorbic acid), VC lyral acetal, DPPH·

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