Tropolone

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Tropolone[1]
Skeletal formula of tropolone
Space-filling model of tropolone
Names
IUPAC name
2-Hydroxy-2,4,6-cycloheptatrien-1-one
Other names
2-Hydroxytropone; Purpurocatechol
Identifiers
533-75-5 YesY
ChEMBL ChEMBL121188 N
ChemSpider 10333 N
EC number 208-577-2
Jmol-3D images Image
KEGG C15474 N
MeSH D014334
PubChem 10789
UNII 7L6DL16P1T N
Properties
C7H6O2
Molar mass 122.12 g/mol
Melting point 50 to 52 °C (122 to 126 °F; 323 to 325 K)
Boiling point 80 to 84 °C (176 to 183 °F; 353 to 357 K) (0.1 mmHg)
Acidity (pKa) 6.89 (and -0.5 for conjugate acid)
Hazards
S-phrases S22 S24/25
Flash point 112 °C (234 °F; 385 K)
Related compounds
Related compounds
Hinokitiol (4-isopropyl-tropolone)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

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]

[3]

References[edit]

  1. ^ Tropolone at Sigma-Aldrich
  2. ^ 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
  3. ^ Chedgy, Russell. Secondary metabolites of Western red cedar (Thuja plicata): their biotechnological applications and role in conferring natural durability. LAP Lambert Academic Publishing, 2010, ISBN 3-8383-4661-0, ISBN 978-3-8383-4661-8