Synthesis, spectroscopic characterization and structural study of 2-isopropenyl-3-methylphenol, carquejiphenol, a carquejol derivative with potential medicinal use

Autores
Minteguiaga, Manuel; Dellacassa, Eduardo; Iramain, Maximiliano Alberto; Catalan, Cesar Atilio Nazareno; Brandan, Silvia Antonia
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this work, 2-isopropenyl-3-methylphenol, hereafter referred to as carquejiphenol (CARP), a minor component of ?carqueja? essential oil, was synthesized starting from carquejol and characterized by using Fourier Transform infrared (FT-IR) and Raman (FT-Raman) spectroscopies, Ultraviolet?Visible (UV?Visible) spectroscopy, Electron Impact Mass spectrometry (EI-MS), Hydrogen and Carbon Nuclear Magnetic Resonance ( 1 H- and 13 C-NMR) and 2D 1 H? 1 H gCOSY, 1 H? 13 C gHSQC, 1 H? 13 C gHMBC experiments. A very good correlation between the predicted FTIR, FTRaman, UV?visible and 1 H? 13 C-NMR spectra for monomer and dimer of CARP by using theoretical B3LYP/6-31G* and 6-311++G** calculations with the corresponding experimental ones was observed. The solvation energies for CARP were predicted by using both levels of calculations and considering the solvent effects with the polarised continuum and solvation models. The increase in volume in solution supports the H bonds formation due to the presence in its structure of an OH group, as revealed by atoms in molecules (AIM) analysis. A high stability for CARP was found by using natural bond orbital (NBO) and AIM studies, while the investigation of the frontier orbitals reveals that CARP is more reactive than carquejol and N-(3,4-dimethoxybenzyl)-hexadecanamide but less reactive than the sesquiterpene lactone cnicin. The proximity of both the electrophilicy and nucleophilicity index of CARP with those obtained respectively for carquejol and for N-(3,4-dimethoxybenzyl)-hexadecanamide, suggests that CARP could probably present pharmacological properties. The scaled quantum mechanical force field (SQMFF) methodology was used to compute the harmonic force fields and to perform the complete vibrational analysis. In this way, 63 normal modes of vibration were assigned and compared with other terpene substances.
Fil: Minteguiaga, Manuel. Universidad de la República; Uruguay
Fil: Dellacassa, Eduardo. Universidad de la República Facultad de Química; Uruguay
Fil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Catalan, Cesar Atilio Nazareno. Universidad Nacional de Tucumán; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucumán; Argentina
Materia
Carquejiphenol
Dft Calculations
Force Field
Molecular Structure
Vibrational Spectra
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/81448
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/81448
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, spectroscopic characterization and structural study of 2-isopropenyl-3-methylphenol, carquejiphenol, a carquejol derivative with potential medicinal useMinteguiaga, ManuelDellacassa, EduardoIramain, Maximiliano AlbertoCatalan, Cesar Atilio NazarenoBrandan, Silvia AntoniaCarquejiphenolDft CalculationsForce FieldMolecular StructureVibrational Spectrahttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this work, 2-isopropenyl-3-methylphenol, hereafter referred to as carquejiphenol (CARP), a minor component of ?carqueja? essential oil, was synthesized starting from carquejol and characterized by using Fourier Transform infrared (FT-IR) and Raman (FT-Raman) spectroscopies, Ultraviolet?Visible (UV?Visible) spectroscopy, Electron Impact Mass spectrometry (EI-MS), Hydrogen and Carbon Nuclear Magnetic Resonance ( 1 H- and 13 C-NMR) and 2D 1 H? 1 H gCOSY, 1 H? 13 C gHSQC, 1 H? 13 C gHMBC experiments. A very good correlation between the predicted FTIR, FTRaman, UV?visible and 1 H? 13 C-NMR spectra for monomer and dimer of CARP by using theoretical B3LYP/6-31G* and 6-311++G** calculations with the corresponding experimental ones was observed. The solvation energies for CARP were predicted by using both levels of calculations and considering the solvent effects with the polarised continuum and solvation models. The increase in volume in solution supports the H bonds formation due to the presence in its structure of an OH group, as revealed by atoms in molecules (AIM) analysis. A high stability for CARP was found by using natural bond orbital (NBO) and AIM studies, while the investigation of the frontier orbitals reveals that CARP is more reactive than carquejol and N-(3,4-dimethoxybenzyl)-hexadecanamide but less reactive than the sesquiterpene lactone cnicin. The proximity of both the electrophilicy and nucleophilicity index of CARP with those obtained respectively for carquejol and for N-(3,4-dimethoxybenzyl)-hexadecanamide, suggests that CARP could probably present pharmacological properties. The scaled quantum mechanical force field (SQMFF) methodology was used to compute the harmonic force fields and to perform the complete vibrational analysis. In this way, 63 normal modes of vibration were assigned and compared with other terpene substances.Fil: Minteguiaga, Manuel. Universidad de la República; UruguayFil: Dellacassa, Eduardo. Universidad de la República Facultad de Química; UruguayFil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Catalan, Cesar Atilio Nazareno. Universidad Nacional de Tucumán; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Brandan, Silvia Antonia. Universidad Nacional de Tucumán; ArgentinaElsevier Science2018-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/81448Minteguiaga, Manuel; Dellacassa, Eduardo; Iramain, Maximiliano Alberto; Catalan, Cesar Atilio Nazareno; Brandan, Silvia Antonia; Synthesis, spectroscopic characterization and structural study of 2-isopropenyl-3-methylphenol, carquejiphenol, a carquejol derivative with potential medicinal use; Elsevier Science; Journal of Molecular Structure; 1165; 8-2018; 332-3430022-2860CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://doi.org/10.1016/j.molstruc.2018.04.001info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022286018304320?via%3Dihubinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-12-23T13:25:54Zoai:ri.conicet.gov.ar:11336/81448instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-12-23 13:25:54.543CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, spectroscopic characterization and structural study of 2-isopropenyl-3-methylphenol, carquejiphenol, a carquejol derivative with potential medicinal use
title Synthesis, spectroscopic characterization and structural study of 2-isopropenyl-3-methylphenol, carquejiphenol, a carquejol derivative with potential medicinal use
spellingShingle Synthesis, spectroscopic characterization and structural study of 2-isopropenyl-3-methylphenol, carquejiphenol, a carquejol derivative with potential medicinal use
Minteguiaga, Manuel
Carquejiphenol
Dft Calculations
Force Field
Molecular Structure
Vibrational Spectra
title_short Synthesis, spectroscopic characterization and structural study of 2-isopropenyl-3-methylphenol, carquejiphenol, a carquejol derivative with potential medicinal use
title_full Synthesis, spectroscopic characterization and structural study of 2-isopropenyl-3-methylphenol, carquejiphenol, a carquejol derivative with potential medicinal use
title_fullStr Synthesis, spectroscopic characterization and structural study of 2-isopropenyl-3-methylphenol, carquejiphenol, a carquejol derivative with potential medicinal use
title_full_unstemmed Synthesis, spectroscopic characterization and structural study of 2-isopropenyl-3-methylphenol, carquejiphenol, a carquejol derivative with potential medicinal use
title_sort Synthesis, spectroscopic characterization and structural study of 2-isopropenyl-3-methylphenol, carquejiphenol, a carquejol derivative with potential medicinal use
dc.creator.none.fl_str_mv Minteguiaga, Manuel
Dellacassa, Eduardo
Iramain, Maximiliano Alberto
Catalan, Cesar Atilio Nazareno
Brandan, Silvia Antonia
author Minteguiaga, Manuel
author_facet Minteguiaga, Manuel
Dellacassa, Eduardo
Iramain, Maximiliano Alberto
Catalan, Cesar Atilio Nazareno
Brandan, Silvia Antonia
author_role author
author2 Dellacassa, Eduardo
Iramain, Maximiliano Alberto
Catalan, Cesar Atilio Nazareno
Brandan, Silvia Antonia
author2_role author
author
author
author
dc.subject.none.fl_str_mv Carquejiphenol
Dft Calculations
Force Field
Molecular Structure
Vibrational Spectra
topic Carquejiphenol
Dft Calculations
Force Field
Molecular Structure
Vibrational Spectra
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this work, 2-isopropenyl-3-methylphenol, hereafter referred to as carquejiphenol (CARP), a minor component of ?carqueja? essential oil, was synthesized starting from carquejol and characterized by using Fourier Transform infrared (FT-IR) and Raman (FT-Raman) spectroscopies, Ultraviolet?Visible (UV?Visible) spectroscopy, Electron Impact Mass spectrometry (EI-MS), Hydrogen and Carbon Nuclear Magnetic Resonance ( 1 H- and 13 C-NMR) and 2D 1 H? 1 H gCOSY, 1 H? 13 C gHSQC, 1 H? 13 C gHMBC experiments. A very good correlation between the predicted FTIR, FTRaman, UV?visible and 1 H? 13 C-NMR spectra for monomer and dimer of CARP by using theoretical B3LYP/6-31G* and 6-311++G** calculations with the corresponding experimental ones was observed. The solvation energies for CARP were predicted by using both levels of calculations and considering the solvent effects with the polarised continuum and solvation models. The increase in volume in solution supports the H bonds formation due to the presence in its structure of an OH group, as revealed by atoms in molecules (AIM) analysis. A high stability for CARP was found by using natural bond orbital (NBO) and AIM studies, while the investigation of the frontier orbitals reveals that CARP is more reactive than carquejol and N-(3,4-dimethoxybenzyl)-hexadecanamide but less reactive than the sesquiterpene lactone cnicin. The proximity of both the electrophilicy and nucleophilicity index of CARP with those obtained respectively for carquejol and for N-(3,4-dimethoxybenzyl)-hexadecanamide, suggests that CARP could probably present pharmacological properties. The scaled quantum mechanical force field (SQMFF) methodology was used to compute the harmonic force fields and to perform the complete vibrational analysis. In this way, 63 normal modes of vibration were assigned and compared with other terpene substances.
Fil: Minteguiaga, Manuel. Universidad de la República; Uruguay
Fil: Dellacassa, Eduardo. Universidad de la República Facultad de Química; Uruguay
Fil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Catalan, Cesar Atilio Nazareno. Universidad Nacional de Tucumán; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucumán; Argentina
description In this work, 2-isopropenyl-3-methylphenol, hereafter referred to as carquejiphenol (CARP), a minor component of ?carqueja? essential oil, was synthesized starting from carquejol and characterized by using Fourier Transform infrared (FT-IR) and Raman (FT-Raman) spectroscopies, Ultraviolet?Visible (UV?Visible) spectroscopy, Electron Impact Mass spectrometry (EI-MS), Hydrogen and Carbon Nuclear Magnetic Resonance ( 1 H- and 13 C-NMR) and 2D 1 H? 1 H gCOSY, 1 H? 13 C gHSQC, 1 H? 13 C gHMBC experiments. A very good correlation between the predicted FTIR, FTRaman, UV?visible and 1 H? 13 C-NMR spectra for monomer and dimer of CARP by using theoretical B3LYP/6-31G* and 6-311++G** calculations with the corresponding experimental ones was observed. The solvation energies for CARP were predicted by using both levels of calculations and considering the solvent effects with the polarised continuum and solvation models. The increase in volume in solution supports the H bonds formation due to the presence in its structure of an OH group, as revealed by atoms in molecules (AIM) analysis. A high stability for CARP was found by using natural bond orbital (NBO) and AIM studies, while the investigation of the frontier orbitals reveals that CARP is more reactive than carquejol and N-(3,4-dimethoxybenzyl)-hexadecanamide but less reactive than the sesquiterpene lactone cnicin. The proximity of both the electrophilicy and nucleophilicity index of CARP with those obtained respectively for carquejol and for N-(3,4-dimethoxybenzyl)-hexadecanamide, suggests that CARP could probably present pharmacological properties. The scaled quantum mechanical force field (SQMFF) methodology was used to compute the harmonic force fields and to perform the complete vibrational analysis. In this way, 63 normal modes of vibration were assigned and compared with other terpene substances.
publishDate 2018
dc.date.none.fl_str_mv 2018-08
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/81448
Minteguiaga, Manuel; Dellacassa, Eduardo; Iramain, Maximiliano Alberto; Catalan, Cesar Atilio Nazareno; Brandan, Silvia Antonia; Synthesis, spectroscopic characterization and structural study of 2-isopropenyl-3-methylphenol, carquejiphenol, a carquejol derivative with potential medicinal use; Elsevier Science; Journal of Molecular Structure; 1165; 8-2018; 332-343
0022-2860
CONICET Digital
CONICET
url http://hdl.handle.net/11336/81448
identifier_str_mv Minteguiaga, Manuel; Dellacassa, Eduardo; Iramain, Maximiliano Alberto; Catalan, Cesar Atilio Nazareno; Brandan, Silvia Antonia; Synthesis, spectroscopic characterization and structural study of 2-isopropenyl-3-methylphenol, carquejiphenol, a carquejol derivative with potential medicinal use; Elsevier Science; Journal of Molecular Structure; 1165; 8-2018; 332-343
0022-2860
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://doi.org/10.1016/j.molstruc.2018.04.001
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022286018304320?via%3Dihub
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.952241

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