Mechanochemical synthesis, characterization and thermoanalytical study of a new curcumin derivative
Autor(a) principal: | |
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Data de Publicação: | 2020 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1007/s10973-020-10000-w http://hdl.handle.net/11449/199096 |
Resumo: | The curcumin is the major constituent of turmeric plant (Curcuma longa), which presents several biological activities such as antioxidant, bactericidal, anti-inflammatory and antitumor. An interesting strategy to improve its properties is to synthetize curcumin derivatives. Thus, the synthesis of a new curcumin derivative (DCUR) with 4-carboxybenzaldehyde (4-CBA) becomes interesting, which occurs by a Knoevenagel reaction, a common methodology used to synthesize curcumin analogues. The synthesis was carried out by the mechanochemical method, which is an efficient green method for the synthesis of organic compounds. The most efficient grinding time for mechanochemical synthesis was determined using PXRD and DSC techniques. 1H NMR, DEPTQ and FTIR analyses confirmed the structure of DCUR. This new methodology is more efficient (at least 5×), and cleaner than usual methods described in the literature to obtain a new compound by Knoevenagel reaction. The TG–DTA, DSC and DSC-microscopy techniques were used to confirm the formation of the compound and to study its thermal behavior. Moreover, the thermoanalytical of 4-CBA showed that this compound presents a reversible solid–solid phase transition. |
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Mechanochemical synthesis, characterization and thermoanalytical study of a new curcumin derivative4-CarboxybenzaldehydeCurcuminoidsKnoevenagel reactionMechanochemistrySolid–solid phase transitionThermal analysisThe curcumin is the major constituent of turmeric plant (Curcuma longa), which presents several biological activities such as antioxidant, bactericidal, anti-inflammatory and antitumor. An interesting strategy to improve its properties is to synthetize curcumin derivatives. Thus, the synthesis of a new curcumin derivative (DCUR) with 4-carboxybenzaldehyde (4-CBA) becomes interesting, which occurs by a Knoevenagel reaction, a common methodology used to synthesize curcumin analogues. The synthesis was carried out by the mechanochemical method, which is an efficient green method for the synthesis of organic compounds. The most efficient grinding time for mechanochemical synthesis was determined using PXRD and DSC techniques. 1H NMR, DEPTQ and FTIR analyses confirmed the structure of DCUR. This new methodology is more efficient (at least 5×), and cleaner than usual methods described in the literature to obtain a new compound by Knoevenagel reaction. The TG–DTA, DSC and DSC-microscopy techniques were used to confirm the formation of the compound and to study its thermal behavior. Moreover, the thermoanalytical of 4-CBA showed that this compound presents a reversible solid–solid phase transition.Chemistry Department School of Sciences UNESP - São Paulo State UniversityChemistry Department School of Sciences UNESP - São Paulo State UniversityUniversidade Estadual Paulista (Unesp)de Moura, Aniele [UNESP]Gaglieri, Caroline [UNESP]da Silva-Filho, Luiz Carlos [UNESP]Caires, Flávio Junior [UNESP]2020-12-12T01:30:39Z2020-12-12T01:30:39Z2020-01-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.1007/s10973-020-10000-wJournal of Thermal Analysis and Calorimetry.1588-29261388-6150http://hdl.handle.net/11449/19909610.1007/s10973-020-10000-w2-s2.0-85087771590Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengJournal of Thermal Analysis and Calorimetryinfo:eu-repo/semantics/openAccess2021-10-23T03:04:05Zoai:repositorio.unesp.br:11449/199096Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T18:17:07.559019Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
Mechanochemical synthesis, characterization and thermoanalytical study of a new curcumin derivative |
title |
Mechanochemical synthesis, characterization and thermoanalytical study of a new curcumin derivative |
spellingShingle |
Mechanochemical synthesis, characterization and thermoanalytical study of a new curcumin derivative de Moura, Aniele [UNESP] 4-Carboxybenzaldehyde Curcuminoids Knoevenagel reaction Mechanochemistry Solid–solid phase transition Thermal analysis |
title_short |
Mechanochemical synthesis, characterization and thermoanalytical study of a new curcumin derivative |
title_full |
Mechanochemical synthesis, characterization and thermoanalytical study of a new curcumin derivative |
title_fullStr |
Mechanochemical synthesis, characterization and thermoanalytical study of a new curcumin derivative |
title_full_unstemmed |
Mechanochemical synthesis, characterization and thermoanalytical study of a new curcumin derivative |
title_sort |
Mechanochemical synthesis, characterization and thermoanalytical study of a new curcumin derivative |
author |
de Moura, Aniele [UNESP] |
author_facet |
de Moura, Aniele [UNESP] Gaglieri, Caroline [UNESP] da Silva-Filho, Luiz Carlos [UNESP] Caires, Flávio Junior [UNESP] |
author_role |
author |
author2 |
Gaglieri, Caroline [UNESP] da Silva-Filho, Luiz Carlos [UNESP] Caires, Flávio Junior [UNESP] |
author2_role |
author author author |
dc.contributor.none.fl_str_mv |
Universidade Estadual Paulista (Unesp) |
dc.contributor.author.fl_str_mv |
de Moura, Aniele [UNESP] Gaglieri, Caroline [UNESP] da Silva-Filho, Luiz Carlos [UNESP] Caires, Flávio Junior [UNESP] |
dc.subject.por.fl_str_mv |
4-Carboxybenzaldehyde Curcuminoids Knoevenagel reaction Mechanochemistry Solid–solid phase transition Thermal analysis |
topic |
4-Carboxybenzaldehyde Curcuminoids Knoevenagel reaction Mechanochemistry Solid–solid phase transition Thermal analysis |
description |
The curcumin is the major constituent of turmeric plant (Curcuma longa), which presents several biological activities such as antioxidant, bactericidal, anti-inflammatory and antitumor. An interesting strategy to improve its properties is to synthetize curcumin derivatives. Thus, the synthesis of a new curcumin derivative (DCUR) with 4-carboxybenzaldehyde (4-CBA) becomes interesting, which occurs by a Knoevenagel reaction, a common methodology used to synthesize curcumin analogues. The synthesis was carried out by the mechanochemical method, which is an efficient green method for the synthesis of organic compounds. The most efficient grinding time for mechanochemical synthesis was determined using PXRD and DSC techniques. 1H NMR, DEPTQ and FTIR analyses confirmed the structure of DCUR. This new methodology is more efficient (at least 5×), and cleaner than usual methods described in the literature to obtain a new compound by Knoevenagel reaction. The TG–DTA, DSC and DSC-microscopy techniques were used to confirm the formation of the compound and to study its thermal behavior. Moreover, the thermoanalytical of 4-CBA showed that this compound presents a reversible solid–solid phase transition. |
publishDate |
2020 |
dc.date.none.fl_str_mv |
2020-12-12T01:30:39Z 2020-12-12T01:30:39Z 2020-01-01 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.1007/s10973-020-10000-w Journal of Thermal Analysis and Calorimetry. 1588-2926 1388-6150 http://hdl.handle.net/11449/199096 10.1007/s10973-020-10000-w 2-s2.0-85087771590 |
url |
http://dx.doi.org/10.1007/s10973-020-10000-w http://hdl.handle.net/11449/199096 |
identifier_str_mv |
Journal of Thermal Analysis and Calorimetry. 1588-2926 1388-6150 10.1007/s10973-020-10000-w 2-s2.0-85087771590 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Journal of Thermal Analysis and Calorimetry |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.source.none.fl_str_mv |
Scopus reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
|
_version_ |
1808128916809842688 |