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Record Information
Version1.0
Creation Date2016-05-27 02:04:09 UTC
Update Date2016-11-09 01:22:41 UTC
Accession NumberCHEM042479
Identification
Common NameΔ9-tetrahydrocannabinolate
ClassSmall Molecule
DescriptionΔ9-tetrahydrocannabinolate is also known as thca or δ9-tetrahydrocannabinolic acid. Δ9-tetrahydrocannabinolate is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Δ9-tetrahydrocannabinolate can be found in a number of food items such as devilfish, arrowhead, potato, and cereals and cereal products, which makes Δ9-tetrahydrocannabinolate a potential biomarker for the consumption of these food products.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
Δ9-tetrahydrocannabinolic acidGenerator
1-Hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-2-carboxylic acidMetaCyc
THCAMetaCyc
Δ9-tetrahydrocannabinolic acidMetaCyc
1-Hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-2-carboxylateGenerator
(6Ar)-2-carboxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-olic acidGenerator
Δ9-tetrahydrocannabinolateGenerator
Chemical FormulaC22H29O4
Average Molecular Mass357.471 g/mol
Monoisotopic Mass357.207 g/mol
CAS Registry NumberNot Available
IUPAC Name(6aR)-2-carboxy-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-olate
Traditional Name(6aR)-2-carboxy-6,6,9-trimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromen-1-olate
SMILES[H][C@@]12CCC(C)=CC1([H])C1=C(OC2(C)C)C=C(CCCCC)C(C(O)=O)=C1[O-]
InChI IdentifierInChI=1S/C22H30O4/c1-5-6-7-8-14-12-17-19(20(23)18(14)21(24)25)15-11-13(2)9-10-16(15)22(3,4)26-17/h11-12,15-16,23H,5-10H2,1-4H3,(H,24,25)/p-1/t15?,16-/m1/s1
InChI KeyUCONUSSAWGCZMV-OEMAIJDKSA-M
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent2,2-dimethyl-1-benzopyrans
Alternative Parents
Substituents
  • 2,2-dimethyl-1-benzopyran
  • Alkyl aryl ether
  • Phenoxide
  • Benzenoid
  • Vinylogous acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.0033 g/LALOGPS
logP4.47ALOGPS
logP6.25ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.59 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity114.54 m³·mol⁻¹ChemAxon
Polarizability41.08 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08fr-0009000000-c6898608247c002a560fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0009000000-781d19b00d63f07a2101View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f72-1983000000-69d22587cf91451f75d1View in MoNA
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 IDNot Available
FooDB IDFDB031309
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID25245187
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available