Styrene (CHEM000229)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2009-03-06 18:58:25 UTC
Update Date2026-03-31 19:41:32 UTC
Accession NumberCHEM000229
Identification
Common NameStyrene
ClassSmall Molecule
DescriptionStyrene is found in alcoholic beverages. Styrene is present in cranberry, bilberry, currants, grapes, vinegar, parsley, milk and dairy products, whisky, cocoa, coffee, tea, roasted filberts and peanuts. Styrene is a flavouring ingredient. Polymers are used in ion-exchange resins in food processing. Indirect food additive arising from adhesives, oatings and packaging materials. Styrene, also known as vinyl benzene, is a colorless oily liquid that evaporates easily and has a sweet smell, although high concentrations confer a less pleasant odor. Styrene is the precursor to polystyrene and several copolymers. Low levels of styrene occur naturally in plants as well as a variety of foods such as fruits, vegetables, nuts, beverages, and meats. (Wikipedia) Styrene has been shown to exhibit signalling and catabolic functions (1, 2). Styrene belongs to the family of Styrenes. These are organic compounds containing an ethenylbenzene moiety.
Contaminant Sources
  • Clean Air Act Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • IARC Carcinogens Group 3
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Cigarette Toxin
  • Food Toxin
  • Household Toxin
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Pollutant
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
EthenylbenzeneChEBI
PhenyletheneChEBI
PhenylethyleneChEBI
StyrenChEBI
StyrolChEBI
VinylbenzeneChEBI
Monomer, styreneMeSH
Styrene monomerMeSH
CinnameneHMDB
CinnamenolHMDB
CinnaminolHMDB
CinnamolHMDB
Ethenyl-benzeneHMDB
Ethenylbenzene, 9ciHMDB
PhenethyleneHMDB
Phenyl-ethyleneHMDB
StyroleneHMDB
Vinyl benzeneHMDB
Vinyl-benzeneHMDB
VinylbenzolHMDB
Chemical FormulaC8H8
Average Molecular Mass104.149 g/mol
Monoisotopic Mass104.063 g/mol
CAS Registry Number100-42-5
IUPAC Nameethenylbenzene
Traditional Namestyrene
SMILESC=CC1=CC=CC=C1
InChI IdentifierInChI=1S/C8H8/c1-2-8-6-4-3-5-7-8/h2-7H,1H2
InChI KeyPPBRXRYQALVLMV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassStyrenes
Direct ParentStyrenes
Alternative Parents
Substituents
  • Styrene
  • Aromatic hydrocarbon
  • Cyclic olefin
  • Unsaturated hydrocarbon
  • Olefin
  • 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 Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-33°C
Boiling PointNot Available
Solubility0.31 mg/mL at 25°C
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP2.92ALOGPS
logP2.71ChemAxon
logS-3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.74 m³·mol⁻¹ChemAxon
Polarizability12.18 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-0900000000-582bcbfa5c258cd958c7Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-0900000000-582bcbfa5c258cd958c7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-9700000000-fcc077c4a70991516aa2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-9000000000-65bc7025d0f253326456Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-004i-9100000000-5280fafb1a35e353dc3dSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 30V, positivesplash10-004i-9200000000-872c7b6ee7f7a539f7acSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 50V, positivesplash10-004i-9200000000-f1c3135a0df129e8ec5fSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 75V, positivesplash10-0fb9-9100000000-c41887824ab40bd09676Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 100V, positivesplash10-0ufr-9000000000-a08dcd64cf252eac173dSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 125V, positivesplash10-0ufr-9000000000-6d6f3165b72ff298647cSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 150V, positivesplash10-0ufr-9000000000-af157200fe186aee0519Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-257f37595a29cd4d0516Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-29144f6013919212fc12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9300000000-55e21db93c2a93dcb229Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-93a8c8c37d30fea4dc59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-1346486826c15e466ac6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-6900000000-9cf38d14243780fea0daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-d9a37da852aa04958c50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9600000000-b66c0ed4c5a2ec64853dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-b463cbf4ba16bde190ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-138b8c24fd394024a31aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-138b8c24fd394024a31aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-73515b4a2a95628c8b69Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-9800000000-1fdcf83a0134198725e5Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (6) ; Inhalation (6) ; Dermal (6)
Mechanism of ToxicityStyrene 7,8-oxide, a metabolite of styrene, can form DNA adducts by binding to deoxyguanosine. It is also mutagenic and causes increased frequency of sister chromatid exchange, chromosomal aberrations, micronucleated cells, and DNA strand breaks. (5)
MetabolismStyrene may be absorbed following ingestion, inhalation, or dermal exposure. It distributes throughout the body in the blood, concentrating in the adipose tissue, kidney, and liver. The primary metabolic pathway is oxidation of the side chain by cytochrome P450 to form styrene 7,8-oxide. Styrene oxide is predominantly metabolized by epoxide hydrolase to form styrene glycol; the styrene glycol is subsequently converted to mandelic acid, phenylglyoxylic acid, and hippuric acid. Styrene 7,8-oxide can also be conjugated with glutathione to ultimately form phenylhydroxylethylmercapturic acids. A minor pathway of styrene metabolism involves the formation of phenylacetaldehyde from styrene 7,8-oxide or cytochrome P450 conversion of styrene to pheylethanol and subsequent metabolism to phenylacetic acid. An alternative minor pathway involves ring oxidation resulting in the production of styrene 3,4-oxide, which is further metabolized to 4-vinylphenol. The metabolites of styrene are excreted mainly in the urine. (8)
Toxicity ValuesLD50: 316 mg/kg (Oral, Mouse) (7) LD50: 898 mg/kg (Intraperitoneal, Rat) (7) LC50: 24 g/m3 over 4 hours (Inhalation, Rat) (7)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (4)
Uses/SourcesStyrene is used to make plastics and rubber. It is a precursor to polystyrene and may be found in insulation, fiberglass, plastic pipes, automobile parts, shoes, drinking cups and other food containers, and carpet backing. Low levels of styrene also occur naturally in a variety of foods such as fruits, vegetables, nuts, beverages, and meats. Small amounts of styrene can be transferred to food from styrene-based packaging material. (5)
Minimum Risk LevelAcute Inhalation: 2 ppm (3) Chronic Inhalation: 0.2 ppm (3) Acute Oral: 0.1 mg/kg/day (3)
Health EffectsStyrene causes nervous system depression and may be carcinogenic. Animals studies have also shown that hearing loss and liver damage may occur. (5, 6)
SymptomsBreathing high levels of styrene may cause nervous system effects such as changes in color vision, tiredness, feeling drunk, slowed reaction time, concentration problems, or balance problems. Chest burning, wheezing, and dyspnea may also occur. Styrene is irritating to the skin, eyes, and respiratory tract. (5, 6)
TreatmentTreatment is mainly symptomatic and supportive. Respiratory assistance may be needed. (6)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0034240
FooDB IDFDB012552
Phenol Explorer IDNot Available
KNApSAcK IDC00037855
BiGG IDNot Available
BioCyc IDCPD-1092
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkStyrene
Chemspider ID7220
ChEBI ID27452
PubChem Compound ID7501
Kegg Compound IDC19506
YMDB IDYMDB16080
ECMDB IDM2MDB004144
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11934013
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24320693
3. Roder-Stolinski C, Fischader G, Oostingh GJ, Feltens R, Kohse F, von Bergen M, Morbt N, Eder K, Duschl A, Lehmann I: Styrene induces an inflammatory response in human lung epithelial cells via oxidative stress and NF-kappaB activation. Toxicol Appl Pharmacol. 2008 Sep 1;231(2):241-7. doi: 10.1016/j.taap.2008.04.010. Epub 2008 Apr 29.
4. Alonso S, Bartolome-Martin D, del Alamo M, Diaz E, Garcia JL, Perera J: Genetic characterization of the styrene lower catabolic pathway of Pseudomonas sp. strain Y2. Gene. 2003 Nov 13;319:71-83.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.