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Tropolone information


Tropolone[1]
Skeletal formula of tropolone
Skeletal formula of tropolone
Space-filling model of tropolone
Space-filling model of tropolone
Names
Preferred IUPAC name
2-Hydroxycyclohepta-2,4,6-trien-1-one
Other names
2-Hydroxytropone; Purpurocatechol
Identifiers
CAS Number
  • 533-75-5 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:79966
ChEMBL
  • ChEMBL121188 checkY
ChemSpider
  • 10333 checkY
ECHA InfoCard 100.007.799 Edit this at Wikidata
EC Number
  • 208-577-2
KEGG
  • C15474 checkY
MeSH D014334
PubChem CID
  • 10789
UNII
  • 7L6DL16P1T checkY
CompTox Dashboard (EPA)
  • DTXSID8049416 Edit this at Wikidata
InChI
  • InChI=1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9) ☒N
    Key: MDYOLVRUBBJPFM-UHFFFAOYSA-N ☒N
  • InChI=1/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)
    Key: MDYOLVRUBBJPFM-UHFFFAOYAW
SMILES
  • C1=CC=C(C(=O)C=C1)O
Properties
Chemical formula
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)
Magnetic susceptibility (χ)
-61·10−6 cm3/mol
Hazards
GHS labelling:[2]
Pictograms
GHS05: CorrosiveGHS07: Exclamation markGHS09: Environmental hazard
Signal word
Danger
Hazard statements
H314, H317, H410
Precautionary statements
P260, P261, P264, P272, P273, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P333+P313, P363, P391, P405, P501
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).
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Infobox references

Tropolone is an organic compound with the chemical formula C7H5(OH)O. It is a pale yellow solid that is soluble in organic solvents. The compound has been of interest to research chemists because of its unusual electronic structure and its role as a ligand precursor. Although not usually prepared from tropone, it can be viewed as its derivative with a hydroxyl group in the 2-position.

  1. ^ Tropolone[permanent dead link] at Sigma-Aldrich
  2. ^ "Tropolone". pubchem.ncbi.nlm.nih.gov.

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Tropolone

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Tropolone is an organic compound with the chemical formula C7H5(OH)O. It is a pale yellow solid that is soluble in organic solvents. The compound has...

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Terpenoid

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sesquiterpenoids. Retinol is a diterpenoid. Hinokitiol is a monoterpenoid, a tropolone derivative. Limonin, a common limonoid, is a triterpenoid. Geosmin is...

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Hinokitiol

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monoterpenoid found in the wood of trees in the family Cupressaceae. It is a tropolone derivative and one of the thujaplicins. Hinokitiol is used in oral and...

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Tropone

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three conjugated alkene groups and a ketone group. The related compound tropolone (2-hydroxy-2,4,6-cycloheptatrien-1-one) has an additional alcohol (or...

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C7H6O2

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Salicylaldehyde (2-hydroxybenzaldehyde) 3-Hydroxybenzaldehyde 4-Hydroxybenzaldehyde Tropolone This set index page lists chemical structure articles associated with...

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Colchicine

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The most important aspect of these derivatives is that they keep the tropolone ring (the ring with the methoxy group and the carbonyl) intact to retain...

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Terpene

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a major consistituent of turpentine. Hinokitiol is a monoterpenoid, a tropolone derivative. Humulene, a sesquiterpene. Taxadiene, a diterpene, precursor...

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Thujaplicin

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Thujaplicin (isopropyl cycloheptatrienolone) is any of three isomeric tropolone-related natural products that have been isolated from the softwoods of...

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Malettinin

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James B.; Wicklow, Donald T. (2003). "Malettinin A: A new antifungal tropolone from an unidentified fungal colonist of Hypoxylon stromata (NRRL 29110)"...

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Monoterpene

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monoterpene Carvone is a monoterpenoid Hinokitiol is a monoterpenoid, a tropolone derivative Linalool is an acyclic monoterpenoid Bicyclic monoterpenes...

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Acyloin condensation

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cyclization reactions to prepare these challenging ring sizes. For example, tropolone is prepared via an initial acyloin condensation that delivers 2-hydroxycycloheptanone:...

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Tyrosinase

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the food industry. Well known tyrosinase inhibitors include kojic acid, tropolone, coumarins, vanillic acid, vanillin, and vanillic alcohol. Lighter skin...

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Thujaplicinol

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Thujaplicinol is either of two isomeric tropolone-related natural products. They are found in tree species primarily in bark, needles, xylem, of the family...

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Tobacco

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Bupicomide Disulfiram Dopastin Fusaric acid Nepicastat Phenopicolinic acid Tropolone PNMTTooltip Phenylethanolamine N-methyltransferase Substrates→Products:...

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Cupressaceae

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known terpenoids found in conifers are sesquiterpenoids, diterpenes and tropolones. Diterpenes are commonly found in different types of conifers and are...

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Wood

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as β-myrcene, are used in the preparation of flavors and fragrances. Tropolones, such as hinokitiol and other thujaplicins, are present in decay-resistant...

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Polyphenol oxidase

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research to eliminate the PPO activity from seedlings of higher plants. Tropolone is a grape polyphenol oxidase inhibitor. Another inhibitor of this enzyme...

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Monoamine oxidase inhibitor

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Bupicomide Disulfiram Dopastin Fusaric acid Nepicastat Phenopicolinic acid Tropolone PNMTTooltip Phenylethanolamine N-methyltransferase Substrates→Products:...

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Thionyl bromide

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(link) Saraf, S. D. (1 August 1969). "Reaction of thionyl bromide with tropolone and phenol". Canadian Journal of Chemistry. 47 (15): 2803–2804. doi:10...

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Tropodithietic acid

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Tropodithietic acid is a tropolone derivative produced by the marine bacteria Phaeobacter piscinae, Phaeobacter inhibens and Phaeobacter gallaeciensis...

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Mepacrine

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Hydralazine

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Methylene blue

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Benserazide

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Carbidopa

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Diphenhydramine

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Tranylcypromine

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Disulfiram

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Bupicomide Disulfiram Dopastin Fusaric acid Nepicastat Phenopicolinic acid Tropolone PNMTTooltip Phenylethanolamine N-methyltransferase Substrates→Products:...

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