Showing Compound Card for Cumene (CDB000586)

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Record Information
Version1.0
Created at2020-03-19 00:45:10 UTC
Updated at2020-12-07 19:07:33 UTC
CannabisDB IDCDB000586
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCumene
DescriptionCumene or Isopropylbenzene, also known as 2-phenylpropane or cumol, belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety. It is a constituent of crude oil and refined fuels. It is a flammable colorless liquid that has a boiling point of 152 °C. Cumene is produced commercially by Friedel–Crafts alkylation of benzene with propylene. Nearly all the cumene that is produced as a pure compound on an industrial scale is converted to cumene hydroperoxide, which is an intermediate in the synthesis of other industrially important chemicals such as phenol and acetone. Isopropylbenzene is also found naturally in many plant foods, such as ceylon cinnamon, herbs and spices, cumin, and ginger. Cumene has also been detected as a volatile component in cannabis plant samples (PMID: 26657499 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(1-Methylethyl)benzeneChEBI
2-PhenylpropaneChEBI
CumolMeSH
(1-Methylethyl)-benzeneHMDB
(1-Methylethyl)benzene (cumene)HMDB
(Methylethyl)benzeneHMDB
(Propan-2-yl)benzeneHMDB
1-Methylethyl-benzeneHMDB
1-Methylethylbenzene, 9ciHMDB
2-FenilpropanoHMDB
2-Fenyl-propaanHMDB
2-Phenyl-propaneHMDB
Benzene, (1-methylethyl)-, oxidized, polyphenyl residuesHMDB
Benzene, (1-methylethyl)-, oxidized, sulfurized by-productsHMDB
Benzene, isopropylHMDB
Benzene,isopropyl cumolHMDB
CumeenHMDB
CumeneHMDB
CUMENE (cumene hydroperoxide (80-15-9))HMDB
I-propyl-benzeneHMDB
I-propylbenzeneHMDB
iso-Propylbenzene (cumene)HMDB
IsopropilbenzeneHMDB
Isopropyl-benzeneHMDB
Isopropyl-benzolHMDB
IsopropylbenzeenHMDB
IsopropylbenzenHMDB
IsopropylbenzolHMDB
Oxidized cumene polyphenyl residuesHMDB
Phenol bottomsHMDB
Polyphenyl residueHMDB
Propane, 2-phenylHMDB
Sulfurized by-product OF cumene oxidationHMDB
IsopropylbenzeneChEBI
Chemical FormulaC9H12
Average Molecular Weight120.19
Monoisotopic Molecular Weight120.0939
IUPAC Name(propan-2-yl)benzene
Traditional Namecumene
CAS Registry Number98-82-8
SMILES
CC(C)C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H12/c1-8(2)9-6-4-3-5-7-9/h3-8H,1-2H3
InChI KeyRWGFKTVRMDUZSP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassCumenes
Direct ParentCumenes
Alternative Parents
Substituents
  • Phenylpropane
  • Cumene
  • Aromatic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

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Role

Environmental role:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-96.9 °CNot Available
Boiling Point152 °CWikipedia
Water Solubility0.061 mg/mL at 25 °CNot Available
logP3.66Not Available
Predicted Properties
PropertyValueSource
logP3.67ALOGPS
logP3.22ChemAxon
logS-3.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.25 m³·mol⁻¹ChemAxon
Polarizability14.82 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)splash10-0a4i-7900000000-34bd38a75dcd3bb2fb0e2014-09-20View Spectrum
GC-MSCumene, non-derivatized, GC-MS Spectrumsplash10-0a4i-5900000000-d7826e94822da05cb9c2Spectrum
GC-MSCumene, non-derivatized, GC-MS Spectrumsplash10-0a4i-5900000000-656039b1dd961fda4904Spectrum
GC-MSCumene, non-derivatized, GC-MS Spectrumsplash10-0a4i-5900000000-b19bd34b1ebead05ac65Spectrum
GC-MSCumene, non-derivatized, GC-MS Spectrumsplash10-0a4i-1900000000-97ac180f6d1c8c215ca1Spectrum
GC-MSCumene, non-derivatized, GC-MS Spectrumsplash10-05fr-2900000000-39c80e40c5435cf05394Spectrum
GC-MSCumene, non-derivatized, GC-MS Spectrumsplash10-0a4i-5900000000-d7826e94822da05cb9c2Spectrum
GC-MSCumene, non-derivatized, GC-MS Spectrumsplash10-0a4i-5900000000-656039b1dd961fda4904Spectrum
GC-MSCumene, non-derivatized, GC-MS Spectrumsplash10-0a4i-5900000000-b19bd34b1ebead05ac65Spectrum
GC-MSCumene, non-derivatized, GC-MS Spectrumsplash10-0a4i-1900000000-97ac180f6d1c8c215ca1Spectrum
GC-MSCumene, non-derivatized, GC-MS Spectrumsplash10-05fr-2900000000-39c80e40c5435cf05394Spectrum
Predicted GC-MSCumene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9800000000-4282a3b73324784a4088Spectrum
Predicted GC-MSCumene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-de6900b5ecae080c15b22016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-280ab4235a4dffc8044f2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pi3-9400000000-58e470689f0010348e802016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-8bb4d370a977170617542016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-92886075d0b76e117cc72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-5900000000-375849fd3939bf16ab912016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-7900000000-835f64dfcaef3b8ebf302021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-9300000000-278676596fcf4bda2bb52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-557a5342da32a2dd8a612021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-794ffb5dd5f7d8f3ef502021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-28d8a72cb103dbe313792021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-b5563824f402728d2a262021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0034029
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012268
KNApSAcK IDC00053958
Chemspider ID7128
KEGG Compound IDC14396
BioCyc IDCPD0-2360
BiGG IDNot Available
Wikipedia LinkCumene
METLIN IDNot Available
PubChem Compound7406
PDB IDNot Available
ChEBI ID34656
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]