Tropolone

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Tropolone[1]
Skeletal formula of tropolone Space-filling model of tropolone
Identifiers
CAS number 533-75-5 YesY
PubChem 10789
ChemSpider 10333 N
UNII 7L6DL16P1T N
EC number 208-577-2
KEGG C15474 N
MeSH D014334
ChEMBL CHEMBL121188 N
Jmol-3D images Image 1
Properties
Molecular formula C7H6O2
Molar mass 122.12 g/mol
Melting point 50–52 °C
Boiling point 80–84 °C (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 noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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