Open AccessButylated methyl caffeate: a novel antioxidant
Author(s) -
Q. Q. Chen,
H. Pasdar,
Xinchu Weng
Publication year - 2020
Publication title -
grasas y aceites
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.384
H-Index - 46
eISSN - 1988-4214
pISSN - 0017-3495
DOI - 10.3989/gya.0226191
Subject(s) - chemistry , caffeic acid , dpph , antioxidant , organic chemistry , butylated hydroxytoluene , methanol , food science , soybean oil , nuclear chemistry
A novel caffeic acid derivative, butylated methyl caffeate (BMC), was synthesized via esterification between butylated caffeic acid (BCA) and methanol. Its antioxidant activity was investigated and compared to TBHQ, caffeic acid (CA), methyl caffeate (MC) and BCA through deep-frying, an oven test in oil-in-water emulsions and DPPH radical scavenging. BMC showed the strongest antioxidant activity among the five antioxidants in emulsions and its antioxidant activity was almost as strong as BCA in frying. Its soybean oil-water partition coefficient was 9.18 due to its ester and tert-butyl groups, far greater than those of MC (4.82), BCA (2.41), CA (0.84) and TBHQ (3.22). This meant that it was much more soluble in the lipid phase than the other four antioxidants in emulsions. The DPPH radical scavenging activity of BMC was near TBHQ, lower than the other three because of its steric hindrance and less functional phenolic hydroxyl groups compared to others when their masses were the same.