Tropolone
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| Names | |
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| IUPAC name
2-Hydroxy-2,4,6-cycloheptatrien-1-one
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| Other names
2-Hydroxytropone; Purpurocatechol
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| Identifiers | |
3D model (JSmol)
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| ECHA InfoCard | 100.007.799 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C7H6O2 | |
| Molar mass | 122.12 g/mol |
| Melting point | 50-52 °C |
| Boiling point | 80-84 °C (0.1 mmHg) |
| Acidity (pKa) | 6.89 |
| Basicity (pKb) | -0.5 |
| Hazards | |
| Flash point | 112 °C |
| Related compounds | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tropolone is a derivative of tropone with a hydroxyl group in the 2-position.
Two methods for the synthesis of tropolone are by bromination of 1,2-cycloheptanedione with N-bromosuccinimide followed by dehydrohalogenation at elevated temperatures and by acyloin condensation of the ethyl ester of pimelic acid the acyloin again followed by oxidation by bromine.
Tropolone synthesis
It is a grape polyphenol oxidase inhibitor.[2]
References
- ^ Tropolone at Sigma-Aldrich
- ^ Time-dependent inhibition of grape polyphenol oxidase by tropolone. Edelmira Valero, Manuela Garcia-Moreno, Ramon Varon and Francisco Garcia-Carmona, J. Agric. Food Chem., 1991, 39 (6), pp 1043–1046, doi:10.1021/jf00006a007