林业科学2018，Vol.54Issue(4)：121-127,7.DOI:10.11707/j.1001-7488.20180414
羟基酪醇快速硝基化及产物波谱表征
A Fast Nitration Reaction of Hydroxytyrosol and Characterization on Its products with Spectroscopy
摘要
Abstract
[Objective] Hydroxytyrosol (HT),belongs to polyphenolic compounds,was widely distributed in olive fruit.Its nitration process is very important for the field of forest products processing industry.Since the traditional method with mixture of concentrated sulfuric acid and nitric acid was easy to make phenolic compound oxidation,and is not an environmentally friendly process.It is thus imperative to find a new fast way to make it nitration,unveiling the product chemical structure by classic multiple spectroscopies in the meantime.[Method] By means of being mixed with NaNO2 under the condition of weak acid and room temperature,hydroxytyrosol was nitrated quickly.The nitro product was characterized by Uv-vis,FTIR,HPLC-MS,1HNMR and 13CNMR.[Result] It was observed that this reaction can be finished in 10 min with pH 3.8 (HAC-NaAC butter solution),achieving yield conversion 99.5％.Also,the maximum adsorption wavelengths of nitro-hydroxytyrosol were 245,296 and 346 nm by Uv-vis spectrophotometer.Phenolic hydroxyl (wavenumber 3 359 cm-1) of hydroxytyrosol as a reactant in the reaction process did not change,and nitro group (wavenumber 1 557 and 1 405 cm-1) was introduced into hydroxytyrosol by the results of FTIR.The chemical structure of reaction product was further confirmed by HPLC-MS,1HNMR and 13CNMR,giving rise to a MW 199 and nitro group linked into para-position of phenolic hydroxyl in hydroxytyrosol.[Conclusion] By means of mild operation conditions (room temperature,pH 3.8 and 10 min),mixing with NaNO2 as a cheap and accessible industrial raw material,hydroxytyrosol is very easy to get nitrated quickly and the nitro group in the product single-located in para-position of phenolic hydroxyl.These will provide a new path for nitro-phenol preparation to replace a traditional method using mixed strong acids,being of an importance.关键词
羟基酪醇/硝基化/产物/波谱特征Key words
hydroxytyrosol/nitration reaction/product/spectroscopy characterization分类
农业科技引用本文复制引用
谢普军,黄立新,张彩虹,丁莎莎,邓叶俊..羟基酪醇快速硝基化及产物波谱表征[J].林业科学,2018,54(4):121-127,7.基金项目
中国林业科学研究院中央级公益性科研院所基本科研业务费专项(CAFYBB2016QA011) （CAFYBB2016QA011）
国家重点研发计划(2016YFD0600800). （2016YFD0600800）
