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      Synthesis of the new 4’-hydroxy-3’-(3-methyl-2-butenyl)chalcone by microwave-assisted condensation of 4-hydroxy-3-(3’-methyl-2’-butenyl) acetophenone isolated from senecio graveolens and benzaldehyde Translated title: Síntesis de la nueva 4’-hidroxi-3’-(3-metil-2-butenil)chalcona por condesación asistida por microondas de 4-hidroxi-3-(3’-metil-2’-butenil) acetofenona aislada a partir de senecio graveolens y benzaldehido


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          In this article we report the synthesis of a new chalcone, 4’-hydroxy-3’-(3-methyl-2-butenyl)chalcone 2, from the organic condensation assisted by microwave irradiation of benzaldehyde and 4-hydroxy-3-(3-methyl-2-butenyl)acetophenone 1, the latter isolated from Senecio graveolens. Compound 2, being of synthetic origin has not been so far isolated from natural sources. Structures were established by modern NMR techniques.

          Translated abstract

          En el presente artículo reportamos la síntesis de una nueva chalcona, 4’-hidroxi-3’-(3-metil-2-butenil)chalcona 2, vía condensación orgánica asistida por irradiación de microondas de benzaldehído y 4-hidroxi-3-(3-metil-2-butenil)acetofenona 1, aislada de la especie vegetal Senecio graveolens. El compuesto 2, que es de origen sintético, no se ha aislado hasta ahora de fuentes naturales. Las estructuras fueron establecidas por técnicas modernas de RMN.

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          Most cited references9

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          The essential oil of Senecio graveolens (Compositae): chemical composition and antimicrobial activity tests.

          The chemical composition of the essential oil obtained from Senecio graveolens (Compositae) was analyzed by GLC-MS and the components identified were: isovaleraldehyde, alpha-pinene, alpha-phellandrene, alpha-terpinene, p-cymene, sabinene, gamma-terpinene, 1-methyl-4-isopropenylbenzene, terpinolene, terpinen-4-ol, piperitenone, alpha- and beta-eudesmol. The investigation by the agar-well diffusion method of the antimicrobial activity of the essential oil proved that it has antibacterial effects on Micrococcus luteus ATCC 9341, oxacillin-sensitive and oxacillin-resistant Staphylococcus aureus, as well as antifungal effects on clinically isolated Candida albicans. The minimal inhibitory concentration (MIC) values for M. luteus, oxacillin-sensitive S. aureus and C. albicans were 8.73, 10.91 and 2.13 x 10(-2) mg/ml, respectively. The antimicrobial activity related to known antibiotics was calculated. These results would be compatible with a potential concentration-dependent selectivity of antifungal effect of S. graveolens essential oil. Minimal bactericidal concentration (MBC) is above 87.3 mg/ml. Thus the MBC:MIC ratio would be clearly higher than 1 (above 8), indicating a bacteriostatic effect of the essential oil.
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            Is Open Access

            Synthesis of novel chalcone derivatives by conventional and microwave irradiation methods and their pharmacological activities

              • Record: found
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              Extraction, characterization and evaluation of antibacterial activity of essential oil of Senecio graveolens Wedd (Wiskataya)


                Author and article information

                Revista Boliviana de Química
                Rev. Bol. Quim
                Universidad Mayor de San Andrés (La Paz, La Paz, Bolivia )
                : 34
                : 3
                : 89-103
                [02] La Paz orgnameUniversidad Mayor de San Andrés UMSA orgdiv1Ciudad Universitaria Cota Cota Bolivia jabravo@ 123456umsa.bo
                [01] La Paz orgnameUniversidad Mayor de San Andrés UMSA orgdiv1Ciudad Universitaria Cota Cota Bolivia jlvila@ 123456umsa.bo
                [03] Potosí orgnameUniversidad Autónoma Tomás Frías UATF orgdiv1Facultad de Ciencias Puras FCP Bolivia quimicauatf@ 123456hotmail.com
                S0250-54602017000300004 S0250-5460(17)03400300004

                This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

                : 29 August 2017
                : 06 August 2017
                Page count
                Figures: 0, Tables: 0, Equations: 0, References: 29, Pages: 15

                SciELO Bolivia

                Original Articles

                4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone,4’-hydroxy-3’-(3-methyl-2-butenyl)chalcone,Microwave-assisted Synthesis,NMR,Green Chemistry,Senecio graveolens,Benzaldehyde,Irradiation,Asteraceae


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