SYNTHESIS OF 5,7-DIMETHYL HESPERETIN

• Main Author: Kurnia, Irhami
• Format: Theses
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/67624
• Institution: Institut Teknologi Bandung

Hesperetin is one of the flavanone group compound which has various biological activities such as anticancer, anticarcinogenic, antioxidant, and has potential as a Covid-19 prophylactic compound. This compound can be isolated from orange peels or green plants, however since it has a low availability in nature, a synthesis method is required. Hesperetin can be prepared using other flavanone-derived synthesis methods, such as the Claisen-Schmidt condensation between benzaldehyde and acetophenone derivatives to produce chalcone and proceed with cyclization. 5,7-dimethyl-hesperetin is an important intermediate compound for obtaining hesperetin. Brevifolin and isovanillin can be used as raw materials to synthesize this compound. The benzylation reaction of isovanillin and brevifolin produced 3-benzyloxy isovanillin and 2-benzyloxy brevifolin with yields of 67% and 60%, respectively. Then, carry out the Claisen-Schmidt reaction with the mechanochemical method between 3-benzyloxy isovanillin and 2-benzyloxy brevifolin to produce 2,3'-dibenzyloxy-4’,4,6-trimethoxy chalcone with a yield of 85%. The debenzylation reaction of 2,3'-dibenzyloxy-4’,4,6-trimethoxy chalcone was carried out under acidic conditions at room temperature and yielded compound 5,7-dimethyl hesperetin with a yield of 39%.