Showing Compound Card for Dehydro-p-cymene (CDB000296)

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Record Information
Version1.0
Created at2020-03-19 00:29:29 UTC
Updated at2020-12-07 19:07:19 UTC
CannabisDB IDCDB000296
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDehydro-p-cymene
Descriptionpara-Mentha-1,3,5,8-tetraene, also known as Dehydro-p-cymene, p-alpha-dimethyl-styrene, Habanene or p-Cymenene, belongs to the class of organic compounds known as phenylpropenes. Phenylpropenes are compounds containing a phenylpropene moiety, which consists of a propene substituent bound to a phenyl group. Dehydro-p-cymene is biochemically a monocyclic monoterpenoid as it is synthesized via isoprene units. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Dehydro-p-cymene is a hydrophobic, neutral molecule that is insoluble in water. It exists as a clear, colorless oil. Dehydro-p-cymene has a herbaceous, leathery, peppery odor with notes of elemi oil and thyme, as well as a touch of citrus. It has an oregano, clove, basalmic, spicy taste. Dehydro-p-cymene is used as a flavoring agent for Italian dishes and for enhancing habanero spices. Dehydro-p-cymene is found in the highest concentration within star anises but it has also been detected in several different foods, such as lemons, coffee, dill, evergreen blackberries, parsley, citrus, sage, spearmint and pepper. Dehydro-p-cymene is one of more than 140 terpenes that are found in cannabis plants (PMID:6991645 ) and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4-IsopropenyltolueneMeSH
1-Isopropenyl-4-methylbenzeneHMDB
1-Methyl-4-(1-methylethenyl)-benzeneHMDB
1-Methyl-4-(1-methylethenyl)benzeneHMDB
1-Methyl-4-(1-methylethenyl)benzene, 9ciHMDB
1-Methyl-4-isopropenylbenzeneHMDB
1-Methyl-4alpha-methylstyreneHMDB
2-(4-Methylphenyl)propeneHMDB
2-(P-Methylphenyl)propeneHMDB
2-P-TolylpropeneHMDB
4-Methyl-alpha-methylstyreneHMDB
4-MethylisopropenylbenzeneHMDB
alpha,4-DimethylstyreneHMDB
alpha,P-DimethylstyreneHMDB
alpha-Dimethyl-P-styreneHMDB
alpha-Methyl-P-methylstyreneHMDB
alpha-P DimethylstyreneHMDB
CymeneneHMDB
dehydro-P-CymeneHMDB
FEMA 3144HMDB
Ghl.PD_Mitscher_leg0.317HMDB
Isopropenyl toluene cHMDB
Methyl-4-(1-methylethenyl)-benzeneHMDB
Methyl-P-isopropenylbenzeneHMDB
P,a-Dimethylstyrene, 8ciHMDB
P,alpha-Dimethyl-styreneHMDB
P,alpha-DimethylstyreneHMDB
P,alpha-DimethylstyrolHMDB
P-alpha-Dimethyl-styreneHMDB
P-alpha-DimethylstyreneHMDB
P-CymeneneHMDB
P-Isopropenyl tolueneHMDB
P-IsopropenyltolueneHMDB
P-Methyl-alpha-methylstyreneHMDB
Para- alpha-dimethylstyreneHMDB
Chemical FormulaC10H12
Average Molecular Weight132.2
Monoisotopic Molecular Weight132.0939
IUPAC Name1-methyl-4-(prop-1-en-2-yl)benzene
Traditional Name1-methyl-4-(prop-1-en-2-yl)benzene
CAS Registry Number1195-32-0
SMILES
CC(=C)C1=CC=C(C)C=C1
InChI Identifier
InChI=1S/C10H12/c1-8(2)10-6-4-9(3)5-7-10/h4-7H,1H2,2-3H3
InChI KeyMMSLOZQEMPDGPI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropenes. Phenylpropenes are compounds containing a phenylpropene moiety, which consists of a propene substituent bound to a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropenes
Direct ParentPhenylpropenes
Alternative Parents
Substituents
  • Phenylpropene
  • Styrene
  • Toluene
  • Aromatic hydrocarbon
  • Branched unsaturated hydrocarbon
  • Cyclic olefin
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

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Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-20 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.79ALOGPS
logP3.52ChemAxon
logS-2.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.07 m³·mol⁻¹ChemAxon
Polarizability16.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-014i-7900000000-8a35d379c53b742012db2015-03-01View Spectrum
Predicted GC-MSDehydro-p-cymene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-5900000000-42122b872bf255e28667Spectrum
Predicted GC-MSDehydro-p-cymene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-1a859e9677580ea17b572016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-2fd4472dcad1e8a7e9492016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-7900000000-c9e2399b68bfd80c5f892016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-564cd5c06312dcea67ff2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-abfffa532b094cd938692016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-3900000000-f77c6849e823907a8ecf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-b6dbb79105fa765a1a392021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-e787ac89e5bc523fe9202021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-4900000000-f20794dba4e302324ade2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1900000000-7a77bd4827fc7193683c2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9300000000-8f432d1b83b7ee6d6dc82021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-b7bc284e37a86692377c2021-09-25View Spectrum
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0029641
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000812
KNApSAcK IDC00010905
Chemspider ID56173
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62385
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]