Evaluación de bases orgánicas para la síntesis de ácido cannabidiólico a partir de cannabidiol

In this research project, the effect of different organic bases and cocatalysts on the synthesis of cannabidiolic acid (CBDA) from cannabidiol (CBD) was evaluated, with the aim of optimizing the reaction yield. The bases used, such as (1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), potassium t-butoxide (...

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Autores:: Silva Mafla, Julian Andrés

Tipo de recurso:: Trabajo de grado de pregrado

Fecha de publicación:: 2024

Institución:: Universidad ICESI

Repositorio:: Repositorio ICESI

Idioma:: spa

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network_name_str	Repositorio ICESI
repository_id_str
dc.title.spa.fl_str_mv	Evaluación de bases orgánicas para la síntesis de ácido cannabidiólico a partir de cannabidiol
title	Evaluación de bases orgánicas para la síntesis de ácido cannabidiólico a partir de cannabidiol
spellingShingle	Evaluación de bases orgánicas para la síntesis de ácido cannabidiólico a partir de cannabidiol Acido cannabidiólico (CBDA) Carboxilación Dióxido de carbono Dbu Trabajo de grado de Química Farmacéutica Cannabidiolic acid (CBDA) Carboxylation Carbon dioxide Dbu
title_short	Evaluación de bases orgánicas para la síntesis de ácido cannabidiólico a partir de cannabidiol
title_full	Evaluación de bases orgánicas para la síntesis de ácido cannabidiólico a partir de cannabidiol
title_fullStr	Evaluación de bases orgánicas para la síntesis de ácido cannabidiólico a partir de cannabidiol
title_full_unstemmed	Evaluación de bases orgánicas para la síntesis de ácido cannabidiólico a partir de cannabidiol
title_sort	Evaluación de bases orgánicas para la síntesis de ácido cannabidiólico a partir de cannabidiol
dc.creator.fl_str_mv	Silva Mafla, Julian Andrés
dc.contributor.advisor.none.fl_str_mv	Pérez Muñoz, Ruby Lizeth Enríquez Valencia, Diego Javier
dc.contributor.author.none.fl_str_mv	Silva Mafla, Julian Andrés
dc.subject.proposal.spa.fl_str_mv	Acido cannabidiólico (CBDA) Carboxilación Dióxido de carbono Dbu Trabajo de grado de Química Farmacéutica
topic	Acido cannabidiólico (CBDA) Carboxilación Dióxido de carbono Dbu Trabajo de grado de Química Farmacéutica Cannabidiolic acid (CBDA) Carboxylation Carbon dioxide Dbu
dc.subject.proposal.eng.fl_str_mv	Cannabidiolic acid (CBDA) Carboxylation Carbon dioxide Dbu
description	In this research project, the effect of different organic bases and cocatalysts on the synthesis of cannabidiolic acid (CBDA) from cannabidiol (CBD) was evaluated, with the aim of optimizing the reaction yield. The bases used, such as (1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), potassium t-butoxide (t-BuOK), and an inorganic base such as sodium hydride (NaH), along with metals such as magnesium, zinc, and nickel, achieved yields between 7.3% and 2.5%. Although these results did not significantly surpass those reported in previous studies, the need arises to optimize the process.
publishDate	2024
dc.date.issued.none.fl_str_mv	2024-12-12
dc.date.accessioned.none.fl_str_mv	2025-06-13T20:40:39Z
dc.date.available.none.fl_str_mv	2025-06-13T20:40:39Z
dc.type.none.fl_str_mv	bachelor thesis
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dc.type.local.none.fl_str_mv	Trabajo de grado
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dc.relation.references.spa.fl_str_mv	Crocq, M. A. History of cannabis and the endocannabinoid system. Dialogues Clin Neurosci 22 , 223 – 228 (2020). Murillo - Rodriguez, E., Pandi - Perumal, S. R. & Montii, J. M. Cannabinoids and Neuropsychiatric Disorders . Advances in Experimental Medicine and Biology http://www.springer.com/series/5584 (2019). Govindarajan, R. K. et al. Biosynthesis of Phytocannabinoids and Structural Insights: A Review. Metabolites vol. 13 Preprint at https://doi.org/10.3390/metabo13030442 (2023). Tahir, M. N., Shahbazi, F., Rondeau - Gagné, S. & Trant, J. F. The biosynthesis of the cannabinoids. Journal of Cannabis Research vol. 3 Preprint at https://doi.org/10.1186/s42238 - 021 - 00062 - 4 (2021). Pose, S. et al. Treatment with high CBDA cannabis Sativa extract reverts autistic - like phenotypes differentially between sexes in two ASD mice models. IBR Neuroscience Reports 15 , (2024). Kleinhenz, M. D. et al. Short term feeding of industrial hemp with a high cannabidiolic acid (CBDA) content increases lying behavior and reduces biomarkers of stress and inflammation in Holstein steers. Sci Rep 12 , (2022). Goerl, B., Watkins, S., Metcalf, C., Smith, M. & Beenhakker, M. Cannabidiolic acid exhibits entourage - like improvements of anticonvulsant activity in an acute rat model of seizures. Epilepsy Res 169 , (2021). Vigli, D., Cosentino, L., Pellas, M. & De Filippis, B. Chronic Treatment with Cannabidiolic Acid (CBDA) Reduces Thermal Pain Sensitivity in Male Mice and Rescues the Hyperalgesia in a Mouse Model of Rett Syndrome. Neuroscience 453 , 113 – 123 (2021). Babayeva, M., Assefa, H., Basu, P. & Loewy, Z. Autism and associated disorders: cannabis as a potential therapy. Frontiers in Bioscience - Elite vol. 14 Preprint at https://doi.org/10.31083/j.fbe1401001 (2022). Kim, J. et al. The Cannabinoids, CBDA and THCA, Rescue Memory Deficits and Reduce Amyloid - Beta and Tau Pathology in an Alzheimer’s Disease - like Mouse Model. Int J Mol Sci 24 , (2023). Gao, B. C. et al. Direct de/carboxylation of cannabidiolic acid (CBDA) and cannabidiol (CBD) from hemp plant material under supercritical CO2. J Asian Nat Prod Res (2024) doi:10.1080/10286020.2024.2345825. Moreno, T., Dyer, P. & Tallon, S. Cannabinoid Decarboxylation: A Comparative Kinetic Study. Ind Eng Chem Res 59 , 20307 – 20315 (2020). Al Ubeed, H. M. S., Bhuyan, D. J., Alsherbiny, M. A., Basu, A. & Vuong, Q. V. A Comprehensive Review on the Techniques for Extraction of Bioactive Compounds from Medicinal Cannabis. Molecules vol. 27 Preprint at https://doi.org/10.3390/molecules27030604 (2022). Zheljazkov, V. D., Noller, J. S., Maggi, F. & Dale, R. Terpenes and Cannabinoids Yields and Profile from Direct - Seeded and Transplanted CBD - Cannabis sativa. J Agric Food Chem 70 , 10417 – 10428 (2022). Luo, J., Preciado, S., Xie, P. & Larrosa, I. Carboxylation of Phenols with CO2 at Atmospheric Pressure. Chemistry - A European Journal 22 , 6798 – 6802 (2016). Sadamitsu, Y., Okumura, A., Saito, K. & Yamada, T. Kolbe - Schmitt type reaction under ambient conditions mediated by an organic base. Chemical Communications 55 , 9837 – 9840 (2019). Yin, X. & Moss, J. R. Recent Developments in the Activation of Carbon Dioxide by Metal Complexes . Coordination Chemistry Reviews vol. 181 (1999). Mechoulam, R. & Ben - Zvi, Z. Carboxylation of resorcinols with methylmagnesium carbonate. Synthesis of cannabinoid acids. (1969). Agudelo, M., Enriquez, D. & Perez, R. L. Nuevo Enfoque Para La Síntesis de Ácido Cannabidiólico a Partir de Cannabidiol Purificado de Cannabis Sativa . (2023). Vogt, C. et al. Understanding carbon dioxide activation and carbon – carbon coupling over nickel. Nat Commun 10 , (2019). Hazari, N., Iwasawa, N. & Hopmann, K. H. Organometallic Chemistry for Enabling Carbon Dioxide Utilization. Organometallics vol. 39 1457 – 1460 Preprint at https://doi.org/10.1021/acs.organomet.0c00229 (2020).
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dc.format.extent.none.fl_str_mv	21 páginas
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dc.publisher.none.fl_str_mv	Universidad Icesi
dc.publisher.faculty.none.fl_str_mv	Barberi de Ingeniería, Diseño y Ciencias Aplicadas
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publisher.none.fl_str_mv	Universidad Icesi
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spelling	Pérez Muñoz, Ruby LizethEnríquez Valencia, Diego JavierSilva Mafla, Julian Andrés1b955d4a-f3b9-4557-bd8f-dd29fdb27ce5-1Cali de Lat: 03 24 00 N degrees minutes Lat: 3.4000 decimal degrees Long: 076 30 00 W degrees minutes Long: -76.5000 decimal degrees.2025-06-13T20:40:39Z2025-06-13T20:40:39Z2024-12-12https://hdl.handle.net/10906/130364https://biblioteca2.icesi.edu.co/cgi-olib/?oid=365038instname:Universidad Icesireponame:Biblioteca Digitalrepourl:https://repository.icesi.edu.co/In this research project, the effect of different organic bases and cocatalysts on the synthesis of cannabidiolic acid (CBDA) from cannabidiol (CBD) was evaluated, with the aim of optimizing the reaction yield. The bases used, such as (1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), potassium t-butoxide (t-BuOK), and an inorganic base such as sodium hydride (NaH), along with metals such as magnesium, zinc, and nickel, achieved yields between 7.3% and 2.5%. Although these results did not significantly surpass those reported in previous studies, the need arises to optimize the process.En este proyecto de investigación, se evaluó el efecto de diferentes bases orgánicas y cocatalizadores en la síntesis de ácido cannabidiólico (CBDA) a partir de cannabidiol (CBD), con el objetivo de optimizar el rendimiento de la reacción. Las bases empleadas como el (1,8- diazabicyclo[5.4.0]undec-7-eno (DBU), t-butóxido de potasio (t-BuOK) y una base inorgánica como el hidruro de sodio (NaH) junto con metales como magnesio, zinc y níquel lograron rendimientos entre 7.3% y 2.5%. Aunque estos resultados no superaron significativamente los reportados en estudios previos, surge la necesidad de optimizar el proceso.Resumen -- Introducción -- Metodología -- Resultados y discusión -- Conclusiones -- Agradecimientos -- Referencias bibliográficas -- AnexosTrabajo de Grado para obtener el título del Programa de Química FarmacéuticaProfesional21 páginasDigitalapplication/pdfspaUniversidad IcesiBarberi de Ingeniería, Diseño y Ciencias AplicadasQuímica FarmacéuticaSantiago de caliEL AUTOR, expresa que la obra objeto de la presente autorización es original y la elaboró sin quebrantar ni suplantar los derechos de autor de terceros, y de tal forma, la obra es de su exclusiva autoría y tiene la titularidad sobre éste. PARÁGRAFO: en caso de queja o acción por parte de un tercero referente a los derechos de autor sobre el artículo, folleto o libro en cuestión, EL AUTOR, asumirá la responsabilidad total, y saldrá en defensa de los derechos aquí autorizados; para todos los efectos, la Universidad Icesi actúa como un tercero de buena fe. Esta autorización, permite a la Universidad Icesi, de forma indefinida, para que en los términos establecidos en la Ley 23 de 1982, la Ley 44 de 1993, leyes y jurisprudencia vigente al respecto, haga publicación de este con fines educativos Todo persona que consulte ya sea la biblioteca o en medio electróico podrá copiar apartes del texto citando siempre la fuentes, es decir el título del trabajo y el autohttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://purl.org/coar/access_right/c_abf2Evaluación de bases orgánicas para la síntesis de ácido cannabidiólico a partir de cannabidiolbachelor thesishttp://purl.org/coar/resource_type/c_7a1fTrabajo de gradoinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/bachelorThesisTodo PúblicoAcido cannabidiólico (CBDA)CarboxilaciónDióxido de carbonoDbuTrabajo de grado de Química FarmacéuticaCannabidiolic acid (CBDA)CarboxylationCarbon dioxideDbuCrocq, M. A. History of cannabis and the endocannabinoid system. Dialogues Clin Neurosci 22 , 223 – 228 (2020).Murillo - Rodriguez, E., Pandi - Perumal, S. R. & Montii, J. M. Cannabinoids and Neuropsychiatric Disorders . Advances in Experimental Medicine and Biology http://www.springer.com/series/5584 (2019).Govindarajan, R. K. et al. Biosynthesis of Phytocannabinoids and Structural Insights: A Review. Metabolites vol. 13 Preprint at https://doi.org/10.3390/metabo13030442 (2023).Tahir, M. N., Shahbazi, F., Rondeau - Gagné, S. & Trant, J. F. The biosynthesis of the cannabinoids. Journal of Cannabis Research vol. 3 Preprint at https://doi.org/10.1186/s42238 - 021 - 00062 - 4 (2021).Pose, S. et al. Treatment with high CBDA cannabis Sativa extract reverts autistic - like phenotypes differentially between sexes in two ASD mice models. IBR Neuroscience Reports 15 , (2024).Kleinhenz, M. D. et al. Short term feeding of industrial hemp with a high cannabidiolic acid (CBDA) content increases lying behavior and reduces biomarkers of stress and inflammation in Holstein steers. Sci Rep 12 , (2022).Goerl, B., Watkins, S., Metcalf, C., Smith, M. & Beenhakker, M. Cannabidiolic acid exhibits entourage - like improvements of anticonvulsant activity in an acute rat model of seizures. Epilepsy Res 169 , (2021).Vigli, D., Cosentino, L., Pellas, M. & De Filippis, B. Chronic Treatment with Cannabidiolic Acid (CBDA) Reduces Thermal Pain Sensitivity in Male Mice and Rescues the Hyperalgesia in a Mouse Model of Rett Syndrome. Neuroscience 453 , 113 – 123 (2021).Babayeva, M., Assefa, H., Basu, P. & Loewy, Z. Autism and associated disorders: cannabis as a potential therapy. Frontiers in Bioscience - Elite vol. 14 Preprint at https://doi.org/10.31083/j.fbe1401001 (2022).Kim, J. et al. The Cannabinoids, CBDA and THCA, Rescue Memory Deficits and Reduce Amyloid - Beta and Tau Pathology in an Alzheimer’s Disease - like Mouse Model. Int J Mol Sci 24 , (2023).Gao, B. C. et al. Direct de/carboxylation of cannabidiolic acid (CBDA) and cannabidiol (CBD) from hemp plant material under supercritical CO2. J Asian Nat Prod Res (2024) doi:10.1080/10286020.2024.2345825.Moreno, T., Dyer, P. & Tallon, S. Cannabinoid Decarboxylation: A Comparative Kinetic Study. Ind Eng Chem Res 59 , 20307 – 20315 (2020).Al Ubeed, H. M. S., Bhuyan, D. J., Alsherbiny, M. A., Basu, A. & Vuong, Q. V. A Comprehensive Review on the Techniques for Extraction of Bioactive Compounds from Medicinal Cannabis. Molecules vol. 27 Preprint at https://doi.org/10.3390/molecules27030604 (2022).Zheljazkov, V. D., Noller, J. S., Maggi, F. & Dale, R. Terpenes and Cannabinoids Yields and Profile from Direct - Seeded and Transplanted CBD - Cannabis sativa. J Agric Food Chem 70 , 10417 – 10428 (2022).Luo, J., Preciado, S., Xie, P. & Larrosa, I. Carboxylation of Phenols with CO2 at Atmospheric Pressure. Chemistry - A European Journal 22 , 6798 – 6802 (2016).Sadamitsu, Y., Okumura, A., Saito, K. & Yamada, T. Kolbe - Schmitt type reaction under ambient conditions mediated by an organic base. Chemical Communications 55 , 9837 – 9840 (2019).Yin, X. & Moss, J. R. Recent Developments in the Activation of Carbon Dioxide by Metal Complexes . Coordination Chemistry Reviews vol. 181 (1999).Mechoulam, R. & Ben - Zvi, Z. Carboxylation of resorcinols with methylmagnesium carbonate. Synthesis of cannabinoid acids. (1969).Agudelo, M., Enriquez, D. & Perez, R. L. Nuevo Enfoque Para La Síntesis de Ácido Cannabidiólico a Partir de Cannabidiol Purificado de Cannabis Sativa . (2023).Vogt, C. et al. Understanding carbon dioxide activation and carbon – carbon coupling over nickel. Nat Commun 10 , (2019).Hazari, N., Iwasawa, N. & Hopmann, K. H. Organometallic Chemistry for Enabling Carbon Dioxide Utilization. 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Evaluación de bases orgánicas para la síntesis de ácido cannabidiólico a partir de cannabidiol

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