2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)- (CHEM012493)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 03:56:49 UTC
Update Date2016-11-09 01:14:35 UTC
Accession NumberCHEM012493
Identification
Common Name2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)-
ClassSmall Molecule
DescriptionA monoterpenoid that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2 and an isopropyl group at position 4. Isolated from Thuja plicata and Chamaecyparis obtusa, it exhibits antimicrobial activities.
Contaminant Sources
  • FooDB Chemicals
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Hydroxy-4-isopropyl-cyclohepta2,4,6-trien-1-oneChEBI
4-IsopropyltropoloneChEBI
HinokitiolChEBI
b-ThujaplicinGenerator
Β-thujaplicinGenerator
2-Hydroxy-4-isopropyl- 2,4,6-cycloheptatriene-1-oneMeSH
beta-Thujaplicin, sodium saltMeSH
2-Hydroxy-4(6)-(1-methylethyl)-2,4,6-cycloheptatrien-1-one, 9ciHMDB
2-Hydroxy-4-(1-methylethyl)-2,4,6-cycloheptatrien-1-oneHMDB
2-Hydroxy-4-isopropyl-2,4, 6-cycloheptatrien-1-oneHMDB
2-Hydroxy-4-isopropyl-2,4,6-cyclohepta-2,4,6-trien-1-oneHMDB
2-Hydroxy-4-isopropyl-2,4,6-cycloheptatrien-1-oneHMDB
2-Hydroxy-4-isopropylcyclohepta-2,4,6-trien-1-oneHMDB
4(6)-IsopropyltropoloneHMDB
4-Isopropyl-tropoloneHMDB
alpha-ThujaplicinHMDB
beta -IsopropyltropolonHMDB
beta -ThujaplicinHMDB
beta -ThujaplicineHMDB
beta-IsopropyltropolonHMDB
beta-IsopropyltropoloneHMDB
beta-ThujaplicineHMDB
Hinokitiol 4-isopropyltropoloneHMDB
HinokitolHMDB
IsopropyltropoloneHMDB
Thujaplicin, betaHMDB
Chemical FormulaC10H12O2
Average Molecular Mass164.201 g/mol
Monoisotopic Mass164.084 g/mol
CAS Registry Number499-44-5
IUPAC Name2-hydroxy-6-(propan-2-yl)cyclohepta-2,4,6-trien-1-one
Traditional Namehinokitiol
SMILESCC(C)C1=CC(=O)C(O)=CC=C1
InChI IdentifierInChI=1S/C10H12O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-7H,1-2H3,(H,11,12)
InChI KeyFUWUEFKEXZQKKA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.21 g/LALOGPS
logP1.8ALOGPS
logP2.06ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)11.44ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity51.55 m³·mol⁻¹ChemAxon
Polarizability17.93 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-2900000000-ff7c6eb395fa0dca0b1cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9660000000-e6364fbc9b1f21523494Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-0a83b777d47c5cb70fe7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0900000000-fb7ac03eae1dde57ce15Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-9600000000-60f1209a7a4a3d467962Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0002-0900000000-fb7ac03eae1dde57ce15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-2cf3a59cab7a65c95fddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1900000000-602677c1a8ab9f590697Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l5-8900000000-a8967686dff6bf46df57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-1825467fa9ff0e5c1aa2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-fe86bc056d5218edfccaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053u-5900000000-4f1700d7e2571d2c2548Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014l-2900000000-478708776defcf78466aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-1900000000-2060bea741e6c07954f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9200000000-b596582d3b5b13942499Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-8db47caa9667c101bd0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-8475534962693d08c77eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9200000000-bb82c060a8ef6dee087cSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0035213
FooDB IDFDB013860
Phenol Explorer IDNot Available
KNApSAcK IDC00003062
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHinokitiol
Chemspider ID3485
ChEBI ID10447
PubChem Compound ID3611
Kegg Compound IDC09904
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10973816
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15917561
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17927050
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18118412
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18379073
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23312825
7. Zhao J, Sakai K: Multiple signalling pathways mediate fungal elicitor-induced beta-thujaplicin biosynthesis in Cupressus lusitanica cell cultures. J Exp Bot. 2003 Feb;54(383):647-56.
8. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.