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Phenolic Acids and Derivatives: Studies on the Relationship among Structure, Radical Scavenging Activity, and Physicochemical Parameters
Open accessAbstract
The antiradical activity of caffeic acid (1), dihydrocaffeic acid (5), and their corresponding n-alkyl esters was evaluated by using the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH(*)) method. Dihydrocaffeic acid (5) was the most potent compound, having an antiradical effect higher than that of (+/-)-alpha-tocopherol, whereas caffeic acid (1) was less efficient. Esterification of the carboxyl group of dihydrocaffeic acid (5) had a dramatic effect on its antiradical potency, but similar effects were not observed for caffeic acid (1) derivatives. The n-alkyl esters of both phenolic series had similar potencies, and their antiradical activities were independent of the alkyl chain length. Dose-dependent scavenger effects were found in both series. Acid-base properties of the compounds, evaluated by using potentiometry and spectrophotometry, showed that the catechol moiety had pK(a2) and pK(a3) values of 9. 24-9.02 and 11.38-10.99 in the dihydrocaffeic series and 8.48-8.24 and 11.38-11.07 in the caffeic series, respectively. Antiradical activity and pK(a) values of the compounds were not related.
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Cites
Structure-antioxidant activity relationships of flavonoids and phenolic acids
Rice-Evans, C. A., Miller, N. J., & Paganga, G. (1996) · Free Radical Biology and Medicine · doi:10.1016/0891-5849(95)02227-9 · Cited by 9,085
Cited by
Filannino, P., Bai, Y., Di Cagno, R., Gobbetti, M., & Gänzle, M. G. (2015) · Food Microbiology · doi:10.1016/j.fm.2014.08.018 · Cited by 354
Antimicrobial and antioxidant properties of phenolic acids alkyl esters
Merkl, R., Hrádková, I., Filip, V., & Šmidrkal, J. (2010) · Czech Journal of Food Sciences · doi:10.17221/132/2010-cjfs · Cited by 278
Cheng, J.-C., Dai, F., Zhou, B., Yang, L., & Liu, Z.-L. (2007) · Food Chemistry · doi:10.1016/j.foodchem.2006.11.012 · Cited by 205
Metadata
- Authors
- Silva, F. A. M., Borges, F., Guimarães, C., Lima, J. L. F. C., Matos, C., & Reis, S.
- Venue
- Journal of Agricultural and Food Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2000-05-02
- Volume
- 48
- Issue
- 6
- Pages
- 2122-2126
- ISSN
- 0021-8561 (ISSN-L)
- 1520-5118
- OpenAlex
- W2035270181
- Cited by
- 374
- References
- 1
- FWCI
- 4.07
- Type
- journal article
- Language
- en
- Open access
- green
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