Catalytic conversion of caffeine into molecules of valuable interest via N-demethylation reaction

Almeida, Flávio V.M.; Díaz de Tuesta, Jose Luis; Gomes, Helder; Guerreiro, Mário C.

Publication

Catalytic conversion of caffeine into molecules of valuable interest via N-demethylation reaction

2023Journal article

dc.contributor.author	Almeida, Flávio V.M.
dc.contributor.author	Díaz de Tuesta, Jose Luis
dc.contributor.author	Gomes, Helder
dc.contributor.author	Guerreiro, Mário C.
dc.date.accessioned	2023-12-18T09:53:17Z
dc.date.available	2023-12-18T09:53:17Z
dc.date.issued	2023
dc.description.abstract	This work aims to apply catalytic processes to promote the conversion of caffeine into valuable dimethylxanthines via N-demethylation reaction. Thus, we seek to evaluate the products formed and propose the reactions involved and their mechanisms. Reaction conditions were evaluated including different concentrations of Fenton reagent and ascorbic acid to evaluate caffeine oxidation. Theobromine, paraxanthine, and theophylline formation was proven by HPLC-DAD and mass spectrometry analysis evidencing the N-demethylation reactions, via radicals, with about 1 % yield. These results open the way for new N-demethylation reaction routes to be studied with applications for caffeine and other biomolecules in diverse areas such as biochemistry and medicinal chemistry. Application of the Fenton catalysis as alternative to promote the conversion of caffeine in other xanthines by N-demethylation. In this scenario was verified the capability of ascorbic acid in promoting same reaction, both environmentally friendly processes. This work investigates the possibility of using a well known biocompound as a precursor to obtain value added molecules.	pt_PT
dc.description.sponsorship	This study was financially supported by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior – Brasil (CAPES) – Finance Code 001 and by CIMO (UIDB/00690/2020) through FEDER under Program PT2020. In addition, the authors acknowledge Central de Análise e Prospecção Química – CAPQ and Laboratório Central de Biologia Molecular (LCBM), Chemistry Department/UFLA for their technical support. Jose L. Diaz De Tuesta acknowledges the financial support through the program of Atracción al Talento of Comunidad de Madrid (Spain) for the individual research grant 2022-T1/AMB-23946.	pt_PT
dc.description.version	info:eu-repo/semantics/publishedVersion	pt_PT
dc.identifier.citation	Almeida, Flávio V.M.; Díaz de Tuesta, Jose Luis; Gomes, Helder; Guerreiro, Mário C. (2023). Catalytic conversion of caffeine into molecules of valuable interest via N-demethylation reaction. ChemistrysSelect. ISSN 2365-6549. 8:43, p. 1-7	pt_PT
dc.identifier.doi	10.1002/slct.202301555	pt_PT
dc.identifier.issn	2365-6549
dc.identifier.uri	http://hdl.handle.net/10198/28959
dc.language.iso	eng	pt_PT
dc.peerreviewed	yes	pt_PT
dc.publisher	Wiley	pt_PT
dc.rights.uri	http://creativecommons.org/licenses/by/4.0/	pt_PT
dc.subject	Ascorbic acid oxidation	pt_PT
dc.subject	Fenton	pt_PT
dc.subject	Nitrogen heterocycles	pt_PT
dc.subject	Radical reactions	pt_PT
dc.subject	Valorization	pt_PT
dc.title	Catalytic conversion of caffeine into molecules of valuable interest via N-demethylation reaction	pt_PT
dc.type	journal article
dspace.entity.type	Publication
oaire.citation.title	ChemistrysSelect	pt_PT
person.familyName	Díaz de Tuesta
person.familyName	Gomes
person.givenName	Jose Luis
person.givenName	Helder
person.identifier.ciencia-id	7A1F-022B-7DBF
person.identifier.ciencia-id	6218-1E19-13EE
person.identifier.orcid	0000-0003-2408-087X
person.identifier.orcid	0000-0001-6898-2408
person.identifier.rid	D-9785-2017
person.identifier.scopus-author-id	55755821600
rcaap.rights	openAccess	pt_PT
rcaap.type	article	pt_PT
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