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This is an early access version, the complete PDF, HTML, and XML versions will be available soon.
Article

Synthesis, Purification, Characterization, and ABTS Antioxidant Evaluation of Novel Azo Dyes

by
Jeremy A. Rodríguez-Vargas
1,
Sebastián H. Díaz-Rodríguez
2,
Víctor G. Vergara-Rodríguez
3,
Ángel Vidal-Rosado
1,
Cristtian Rivera-Torres
2,
Alejandra Ríos-Rodríguez
1,
Martín Rodríguez-Del Valle
2,
Daliana Agosto-Disdier
1,
Marielys Torres-Díaz
1,
Kai H. Griebenow
1 and
Raúl R. Rodríguez-Berríos
1,*
1
Department of Chemistry, University of Puerto Rico, Rio Piedras Campus, 17 Ave. Universidad Ste 1701, San Juan 00925-2537, Puerto Rico
2
Department of Biology, University of Puerto Rico, Rio Piedras Campus, 17 Ave. Universidad Ste 1701, San Juan 00925-2537, Puerto Rico
3
Department of Interdisciplinary Studies, University of Puerto Rico, Rio Piedras Campus, 17 Ave. Universidad Ste 1701, San Juan 00925-2537, Puerto Rico
*
Author to whom correspondence should be addressed.
Organics 2025, 6(3), 39; https://doi.org/10.3390/org6030039
Submission received: 21 May 2025 / Revised: 26 August 2025 / Accepted: 28 August 2025 / Published: 2 September 2025
Versions Notes

Abstract

The search for bioactive compounds with antioxidant properties is critical in combating oxidative stress-related diseases and advancing novel therapeutic agents. Azo dyes, traditionally used in textiles, food, and cosmetics, have recently attracted attention due to their emerging biological activities, including antioxidant potential. In this study, we synthesized and characterized 267 azo dyes derived from natural phenolic cores such as salicylic acid, syringol, and 5,6,7,8-tetrahydro-2-naphthol. Eighteen of these compounds are novel. Structural characterization was performed using NMR, UV-Vis, IR spectroscopy, and mass spectrometry. Antioxidant activity was assessed using in vitro assays with ABTS radical scavenging method. SAR analysis revealed that dyes derived from syringol and 5, 6, 7, 8-tetrahydro-2-naphthol showed the most consistent and potent antioxidant activity. Notably, azo dyes bearing fluoro and nitro substituents in the para position exhibited the lowest IC50 values, highlighting the influence of electron-withdrawing groups and substitution patterns on antioxidant behavior. This work establishes a precedent for SAR-driven evaluation of azo dyes using ABTS and supports their further exploration as functional antioxidant agents in medicinal chemistry.
Keywords: azo dyes; antioxidant activity; structure–activity relationship (sar); ABTS assay; electron-withdrawing groups; phenolic compounds; syringol; 5,6,7,8-Tetrahydro-2-naphthol azo dyes; antioxidant activity; structure–activity relationship (sar); ABTS assay; electron-withdrawing groups; phenolic compounds; syringol; 5,6,7,8-Tetrahydro-2-naphthol

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MDPI and ACS Style

Rodríguez-Vargas, J.A.; Díaz-Rodríguez, S.H.; Vergara-Rodríguez, V.G.; Vidal-Rosado, Á.; Rivera-Torres, C.; Ríos-Rodríguez, A.; Rodríguez-Del Valle, M.; Agosto-Disdier, D.; Torres-Díaz, M.; Griebenow, K.H.; et al. Synthesis, Purification, Characterization, and ABTS Antioxidant Evaluation of Novel Azo Dyes. Organics 2025, 6, 39. https://doi.org/10.3390/org6030039

AMA Style

Rodríguez-Vargas JA, Díaz-Rodríguez SH, Vergara-Rodríguez VG, Vidal-Rosado Á, Rivera-Torres C, Ríos-Rodríguez A, Rodríguez-Del Valle M, Agosto-Disdier D, Torres-Díaz M, Griebenow KH, et al. Synthesis, Purification, Characterization, and ABTS Antioxidant Evaluation of Novel Azo Dyes. Organics. 2025; 6(3):39. https://doi.org/10.3390/org6030039

Chicago/Turabian Style

Rodríguez-Vargas, Jeremy A., Sebastián H. Díaz-Rodríguez, Víctor G. Vergara-Rodríguez, Ángel Vidal-Rosado, Cristtian Rivera-Torres, Alejandra Ríos-Rodríguez, Martín Rodríguez-Del Valle, Daliana Agosto-Disdier, Marielys Torres-Díaz, Kai H. Griebenow, and et al. 2025. "Synthesis, Purification, Characterization, and ABTS Antioxidant Evaluation of Novel Azo Dyes" Organics 6, no. 3: 39. https://doi.org/10.3390/org6030039

APA Style

Rodríguez-Vargas, J. A., Díaz-Rodríguez, S. H., Vergara-Rodríguez, V. G., Vidal-Rosado, Á., Rivera-Torres, C., Ríos-Rodríguez, A., Rodríguez-Del Valle, M., Agosto-Disdier, D., Torres-Díaz, M., Griebenow, K. H., & Rodríguez-Berríos, R. R. (2025). Synthesis, Purification, Characterization, and ABTS Antioxidant Evaluation of Novel Azo Dyes. Organics, 6(3), 39. https://doi.org/10.3390/org6030039

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