Synthesis and crystal structure of 5,10-dihydroxy-9-methoxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one
5,10-Dihydroxy-9-methoxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one, C24H24O6 (2), is a prenylated xanthone that was synthesized from 5,9,10-trihydroxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one or macluraxanthone (1), a known compound isol...
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International Union of Crystallography
2025-03-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
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| Online Access: | https://journals.iucr.org/paper?S2056989025001070 |
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| author | Amporn Saekee Chutima Kuhakarn Khetpakorn Chakarawet Sakchai Hongthong |
| author_facet | Amporn Saekee Chutima Kuhakarn Khetpakorn Chakarawet Sakchai Hongthong |
| author_sort | Amporn Saekee |
| collection | DOAJ |
| description | 5,10-Dihydroxy-9-methoxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one, C24H24O6 (2), is a prenylated xanthone that was synthesized from 5,9,10-trihydroxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one or macluraxanthone (1), a known compound isolated from Garcinia schomburgkiana Pierre. The present study describes the synthesis of compound 2 by methylation reaction of 1, and its crystallographic characterization. Compound 2 features a planar xanthone core and a bent pyrano ring adopting a half-boat conformation. An intermolecular O—H...O hydrogen bond between the hydroxyl hydrogen donor and the ketone acceptor organizes the molecules into a one-dimensional network along the b-axis direction. Perpendicular to this network, π–π stacking interactions form the three-dimensional supramolecular architecture. These two key intermolecular interactions are distinctly revealed in the Hirshfeld surface analysis. |
| format | Article |
| id | doaj-art-ecfcd143b0504d67b3cd7ffdfc69ebe2 |
| institution | OA Journals |
| issn | 2056-9890 |
| language | English |
| publishDate | 2025-03-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj-art-ecfcd143b0504d67b3cd7ffdfc69ebe22025-08-20T01:57:28ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902025-03-0181321922310.1107/S2056989025001070dx2063Synthesis and crystal structure of 5,10-dihydroxy-9-methoxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-oneAmporn Saekee0Chutima Kuhakarn1Khetpakorn Chakarawet2Sakchai Hongthong3Department of Chemistry and Center of Excellence for Innovation in Chemistry, (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok 10400, ThailandDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok 10400, ThailandDepartment of Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, ThailandProgram in Chemistry, Faculty of Science and Technology, Rajabhat Rajanagarindra University, Chachoengsao 24000, Thailand5,10-Dihydroxy-9-methoxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one, C24H24O6 (2), is a prenylated xanthone that was synthesized from 5,9,10-trihydroxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one or macluraxanthone (1), a known compound isolated from Garcinia schomburgkiana Pierre. The present study describes the synthesis of compound 2 by methylation reaction of 1, and its crystallographic characterization. Compound 2 features a planar xanthone core and a bent pyrano ring adopting a half-boat conformation. An intermolecular O—H...O hydrogen bond between the hydroxyl hydrogen donor and the ketone acceptor organizes the molecules into a one-dimensional network along the b-axis direction. Perpendicular to this network, π–π stacking interactions form the three-dimensional supramolecular architecture. These two key intermolecular interactions are distinctly revealed in the Hirshfeld surface analysis.https://journals.iucr.org/paper?S2056989025001070crystal structurexanthonenatural products |
| spellingShingle | Amporn Saekee Chutima Kuhakarn Khetpakorn Chakarawet Sakchai Hongthong Synthesis and crystal structure of 5,10-dihydroxy-9-methoxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one Acta Crystallographica Section E: Crystallographic Communications crystal structure xanthone natural products |
| title | Synthesis and crystal structure of 5,10-dihydroxy-9-methoxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one |
| title_full | Synthesis and crystal structure of 5,10-dihydroxy-9-methoxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one |
| title_fullStr | Synthesis and crystal structure of 5,10-dihydroxy-9-methoxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one |
| title_full_unstemmed | Synthesis and crystal structure of 5,10-dihydroxy-9-methoxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one |
| title_short | Synthesis and crystal structure of 5,10-dihydroxy-9-methoxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one |
| title_sort | synthesis and crystal structure of 5 10 dihydroxy 9 methoxy 2 2 dimethyl 12 2 methylbut 3 en 2 yl 2h 6h pyrano 3 2 b xanthen 6 one |
| topic | crystal structure xanthone natural products |
| url | https://journals.iucr.org/paper?S2056989025001070 |
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