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Synthesis of Chalcone Derivative from Clove Leaf Waste as a Natural Antioxidant
Pharmaceutical Chemistry Journal ( IF 0.8 ) Pub Date : 2021-06-14 , DOI: 10.1007/s11094-021-02410-3
Willy Tirza Eden , Dante Alighiri , Nanik Wijayati , Sri Mursiti

The synthesis of chalcone derivatives from clove leaf waste and their potential application as natural antioxidants have been studied. Synthesis of chalcone derivatives takes six steps: (1) distillation of clove leaf oil waste, (2) isolation of eugenol from clove leaf oil, (3) isomerization reaction of eugenol to produce isoeugenol, (4) oxidation reaction of isoeugenol to produce vanillin, (5) O-allylation reaction of vanillin to produce 4-allyloxy-3-methoxy benzaldehyde, and (6) Claisen-Schmidt condensation reaction of compound 5 with acetophenone to yield 3-(4-allyloxy-3-methoxyphenyl)-1-phenyl prop-2-en-1-one as chalcone derivative of target molecule in 97.28% yield. The antioxidant activity was evaluated in oleic acid oxidation reaction in comparison to butylated hydroxytoluene (BHT) as a standard by using ferric thiocyanate (FTC) and thiobarbituric acid (TBA) methods. The test showed that the order of antioxidant activity was as follows : BHT > 3-(4-allyloxy-3-methoxyphenyl)-1-phenyl prop-2-en-1-one > vanillin > 4-allyloxy-3-methoxy benzaldehyde.



中文翻译:

丁香叶废料中查尔酮衍生物作为天然抗氧化剂的合成

已经研究了从丁香叶废料中合成查耳酮衍生物及其作为天然抗氧化剂的潜在应用。查耳酮衍生物的合成分六个步骤:( 1 )丁香叶油废料的蒸馏,( 2 )丁香叶油中丁香酚的分离,( 3 )丁香酚异构化反应生成异丁香酚,( 4 )异丁香酚氧化反应生成香兰素, ( 5 )香兰素O-烯丙基化反应生成4-烯丙氧基-3-甲氧基苯甲醛,( 6 )化合物5的Claisen-Schmidt缩合反应与苯乙酮生成 3-(4-allyloxy-3-甲氧基苯基)-1-苯基 prop-2-en-1-one 作为目标分子的查耳酮衍生物,产率为 97.28%。通过使用硫氰酸铁 (FTC) 和硫代巴比妥酸 (TBA) 方法,与作为标准的丁基化羟基甲苯 (BHT) 相比,在油酸氧化反应中评估了抗氧化活性。测试表明抗氧化活性的顺序为:BHT > 3-(4-allyloxy-3-methoxyphenyl)-1-phenyl prop-2-en-1-one > vanillin > 4-allyloxy-3-methoxy benzaldehyde .

更新日期:2021-06-14
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