Revisiting curcumin chemistry part I: a new strategy for the synthesis of curcuminoids.
Revisiting curcumin chemistry part I: a new strategy for the synthesis of curcuminoids.
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DOI：
10.4103/0250-474x.93508
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发表时间：
2011-05
影响因子：
0.5
通讯作者：
Sudheer P
中科院分区：
文献类型：
--
作者：
Rao EV;Sudheer P
本文报道了一种合成姜黄素类化合物的新方法，即在正丁胺催化下，乙酰丙酮二氟硼酸盐与芳香醛反应。对称取代的姜黄素类化合物如姜黄素和双脱甲氧基姜黄素的新中间体姜黄素二氟硼酸盐稳定，可以用aq.甲醇pH5.8，得到高纯度的姜黄素类化合物。该方法也适用于不对称的姜黄素类化合物，如脱甲氧基姜黄素，并进行了一些涉及柱色谱的修改。首次合成了姜黄素类二氟硼酸盐中间体和天然β-二酮硼氢化钠二氟硼酸盐，并对其理化性质和光谱数据进行了表征。指出了用三氟化硼保护乙酰丙酮中烯醇基的优点。解释了使用纯姜黄素进行生物活性研究的重要性。
A new strategy for the synthesis of curcuminoids is described involving the reaction of acetylacetone difluroboronite with an aromatic aldehyde in the presence of n-butylamine as catalyst. The new intermediate products, curcuminoid difluroboronites, of symmetrically substituted curcuminoids like curcumin and bisdemethoxycurcumin are stable, can be isolated and hydrolysed with aq. methanol at pH 5.8 to get the curcuminoids of high purity. The method is applicable for unsymmetrical curcuminoids like demethoxycurcumin also with some modification involving column chromatography. The intermediate curcuminoid difluroboronites, as also the natural β-diketone pongamol difluroboronite, prepared for the first time were characterized on the basis of physical and chemical properties and spectroscopic data. The advantage of using borontrifluoride to protect the enol group in acetylacetone over the generally used boric oxide is brought out. The importance of conducting biological activity studies using pure curcuminoids is explained.