Showing Compound Card for Tropolone (CDB005669)

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Record Information
Version1.0
Created at2020-04-27 16:43:51 UTC
Updated at2021-01-04 18:49:07 UTC
CannabisDB IDCDB005669
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameTropolone
DescriptionTropolone also known as Purpurocatechol belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing a tropone ring with a hydroxyl group at ring position 2. Tropolone is a hydroxylated derivative of tropone in which the hydroxyl group is substituted at C-2 of the tropone. Tropolone is a pale-yellow solid with a melting point of 51 oC that is soluble in organic solvents. Tropolone is found in black tea (https://doi.org/10.1021%2Fcr60284a002), grapes (as an inhibitor of polyphenol oxidase) ( Ref:DOI ) and in mushrooms (as an inhibitor of tyrosinase) ( Ref:DOI ). Tropolone is synthesized via a polyketide pathway, which affords a phenolic intermediate that undergoes ring expansion from a six to a seven-membered ring. Tropolone exhibits bactericidal activity and targets a wide variety of gram-positive and gram-negative bacteria (PMID: 1147585 ). Tropolone is also found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Hydroxy-2,4,6-cycloheptatrien-1-oneChEBI
2-Hydroxycyclohepta-2,4,6-trienoneChEBI
2-HydroxytroponeChEBI
PurpurocatecholChEBI
Chemical FormulaC7H6O2
Average Molecular Weight122.12
Monoisotopic Molecular Weight122.0368
IUPAC Name2-hydroxycyclohepta-2,4,6-trien-1-one
Traditional Nametropolone
CAS Registry Number533-75-5
SMILES
OC1=CC=CC=CC1=O
InChI Identifier
InChI=1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)
InChI KeyMDYOLVRUBBJPFM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2.
KingdomOrganic compounds
Super ClassHydrocarbon derivatives
ClassTropones
Sub ClassTropolones
Direct ParentTropolones
Alternative Parents
Substituents
  • Tropolone
  • Cyclic ketone
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point50 to 52 °CWikipedia
Boiling Point80 to 84 °C at 0.1 mmHgWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.07ALOGPS
logP1.09ChemAxon
logS-0.71ALOGPS
pKa (Strongest Acidic)11.26ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.12 m³·mol⁻¹ChemAxon
Polarizability11.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSTropolone, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTropolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-8900000000-6ecfbb0f58c76ee8c14eSpectrum
Predicted GC-MSTropolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTropolone, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-c437e8c86668124c518c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-d1bb6ef1743719754ac72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr6-9200000000-37fb95523cb619f42ff02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-efaea1769aac41897ae32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2900000000-b9402725c0c171be03cc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0296-9100000000-96980092b6b1093864632016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0259299
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00011964
Chemspider ID10333
KEGG Compound IDC15474
BioCyc IDCPD-7024
BiGG IDNot Available
Wikipedia LinkTropolone
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID79966
References
General References
  1. Trust TJ: Antibacterial activity of tropolone. Antimicrob Agents Chemother. 1975 May;7(5):500-6. doi: 10.1128/aac.7.5.500. [PubMed:1147585 ]