Isopropylbenzene (T3D3468)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2009-07-30 17:58:32 UTC
Update Date2014-12-24 20:26:06 UTC
Accession NumberT3D3468
Identification
Common NameIsopropylbenzene
ClassSmall Molecule
DescriptionIsopropylbenzene is found in ceylan cinnamon. Isopropylbenzene is a trace constituent of ginger oil (Zingiber officinale) Cumene is the common name for isopropylbenzene, an organic compound that is an aromatic hydrocarbon. It is a constituent of crude oil and refined fuels. It is a flammable colorless liquid that has a boiling point of 152 C. 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 has been shown to exhibit catabolic function (3).
Compound Type
  • Food Toxin
  • Gasoline Additive/Component
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Pollutant
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
(1-methylethyl)-Benzene
(1-Methylethyl)benzene
(1-methylethyl)benzene (cumene)
(methylethyl)benzene
(propan-2-yl)benzene
1-Methylethyl-Benzene
1-Methylethylbenzene, 9CI
2-Fenilpropano
2-Fenyl-propaan
2-Phenyl-Propane
2-Phenylpropane
Benzene, (1-methylethyl)-, oxidized, polyphenyl residues
Benzene, (1-methylethyl)-, oxidized, sulfurized by-products
Benzene, isopropyl
Benzene,isopropyl cumol
Cumeen
Cumene
CUMENE (CUMENE HYDROPEROXIDE (80-15-9))
Cumol
I-Propyl-Benzene
I-Propylbenzene
Iso-propylbenzene (cumene)
Isopropilbenzene
Isopropyl-Benzene
Isopropyl-benzol
Isopropylbenzeen
Isopropylbenzen
Isopropylbenzol
Oxidized cumene polyphenyl residues
Phenol bottoms
Polyphenyl residue
Propane, 2-phenyl
Sulfurized BY-product of cumene oxidation
Chemical FormulaC9H12
Average Molecular Mass120.192 g/mol
Monoisotopic Mass120.094 g/mol
CAS Registry Number98-82-8
IUPAC Name(propan-2-yl)benzene
Traditional Namecumene
SMILESCC(C)C1=CC=CC=C1
InChI IdentifierInChI=1S/C9H12/c1-8(2)9-6-4-3-5-7-9/h3-8H,1-2H3
InChI KeyInChIKey=RWGFKTVRMDUZSP-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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-96.9°C
Boiling PointNot Available
Solubility0.0613 mg/mL at 25°C
LogP3.66
Predicted Properties
PropertyValueSource
Water Solubility0.037 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-d7826e94822da05cb9c22017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-656039b1dd961fda49042017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-b19bd34b1ebead05ac652017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-1900000000-97ac180f6d1c8c215ca12017-09-12View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-05fr-2900000000-39c80e40c5435cf053942017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-d7826e94822da05cb9c22018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-656039b1dd961fda49042018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-b19bd34b1ebead05ac652018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-1900000000-97ac180f6d1c8c215ca12018-05-18View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-05fr-2900000000-39c80e40c5435cf053942018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9800000000-4282a3b73324784a40882016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-de6900b5ecae080c15b22016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-280ab4235a4dffc8044f2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pi3-9400000000-58e470689f0010348e802016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-8bb4d370a977170617542016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-92886075d0b76e117cc72016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-5900000000-375849fd3939bf16ab912016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-7900000000-835f64dfcaef3b8ebf302021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-9300000000-278676596fcf4bda2bb52021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-557a5342da32a2dd8a612021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-794ffb5dd5f7d8f3ef502021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-28d8a72cb103dbe313792021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-b5563824f402728d2a262021-09-24View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-7900000000-34bd38a75dcd3bb2fb0e2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureOral (10) ; inhalation (10) ; dermal (10)
Mechanism of ToxicityPetroleum distillates are central nervous system depressants and cause pulmonary damage. (1)
MetabolismVolatile hydrocarbons are absorbed mainly through the lungs, and may also enter the body after ingestion via aspiration. (1)
Toxicity ValuesLD50: 1400 mg/kg (Oral, Rat) (4) LC50: 24 700 mg/m3 over 2 hours (Inhalation, Mouse) (4)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (11)
Uses/SourcesIsopropylbenzene is a component of gasoline. 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. (9)
Minimum Risk LevelNot Available
Health EffectsPetroleum distillates are aspiration hazards and may cause pulmonary damage, central nervous system depression, and cardiac effects such as cardiac arrhythmias. They may also affect the blood, immune system, liver, and kidney. (1, 8)
SymptomsPetroleum distillate poisoning may cause nausea, vomiting, cough, pulmonary irritation progressing to pulmonary edema, bloody sputum, and bronchial pneumonia. At high amounts, central nervous system depression may also occur, with symptoms such as weakness, dizziness, slow and shallow respiration, unconsciousness, and convulsions. Petroleum distillates are also irritating to the skin. (2)
TreatmentTreatment is mainly symptomatic and supportive. Gastric lavage, emesis, and the administration of activated charcoal should be avoided, as vomiting increases the risk of aspiration. (1)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB34029
PubChem Compound ID7406
ChEMBL IDCHEMBL1398949
ChemSpider ID7128
KEGG IDC14396
UniProt IDNot Available
OMIM ID
ChEBI ID34656
BioCyc IDCPD-1125
CTD IDNot Available
Stitch IDIsopropylbenzene
PDB IDNot Available
ACToR ID1773
Wikipedia LinkIsopropylbenzene
References
Synthesis ReferenceNot Available
MSDST3D3468.pdf
General References
  1. Gunther S, McMillan PJ, Wallace LJ, Muller S: Plasmodium falciparum possesses organelle-specific alpha-keto acid dehydrogenase complexes and lipoylation pathways. Biochem Soc Trans. 2005 Nov;33(Pt 5):977-80. [16246025 ]
  2. Perham RN: Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions. Annu Rev Biochem. 2000;69:961-1004. [10966480 ]
  3. Eaton RW, Timmis KN: Characterization of a plasmid-specified pathway for catabolism of isopropylbenzene in Pseudomonas putida RE204. J Bacteriol. 1986 Oct;168(1):123-31. [3019995 ]
  4. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  5. Dreisbach, RH (1983). Handbook of Poisoning. Los Altos, California: Lange Medical Publications.
  6. MICROMEDEX Thomson Health Care (2002). USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. Englewood, CO: MICROMEDEX Thomson Health Care. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc.
  7. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  8. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for total petroleum hydrocarbons (TPH). U.S. Public Health Service in collaboration with U.S. [Link]
  9. Wikipedia. Cumene. Last Updated 21 May 2009. [Link]
  10. Wikipedia. Lead telluride. Last Updated 8 May 2009. [Link]
  11. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available