Styrene (T3D0271)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-03-06 18:58:25 UTC
Update Date2014-12-24 20:21:26 UTC
Accession NumberT3D0271
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.
Compound 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
Synonym
Cinnamene
Cinnamenol
Cinnaminol
Cinnamol
Ethenyl-Benzene
Ethenylbenzene
Phenethylene
Phenyl-Ethylene
Phenylethene
Phenylethylene
Styrol
Styrolene
Vinyl benzene
Vinyl-Benzene
Vinylbenzene
Vinylbenzol
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 KeyInChIKey=PPBRXRYQALVLMV-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
LogP2.95
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-0900000000-582bcbfa5c258cd958c72017-09-12View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-0900000000-582bcbfa5c258cd958c72018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-9700000000-fcc077c4a70991516aa22016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-9000000000-65bc7025d0f2533264562020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-004i-9100000000-5280fafb1a35e353dc3d2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 30V, positivesplash10-004i-9200000000-872c7b6ee7f7a539f7ac2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 50V, positivesplash10-004i-9200000000-f1c3135a0df129e8ec5f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 75V, positivesplash10-0fb9-9100000000-c41887824ab40bd096762020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 100V, positivesplash10-0ufr-9000000000-a08dcd64cf252eac173d2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 125V, positivesplash10-0ufr-9000000000-6d6f3165b72ff298647c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 150V, positivesplash10-0ufr-9000000000-af157200fe186aee05192020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-257f37595a29cd4d05162016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-29144f6013919212fc122016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9300000000-55e21db93c2a93dcb2292016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-93a8c8c37d30fea4dc592016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-1346486826c15e466ac62016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-6900000000-9cf38d14243780fea0da2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-d9a37da852aa04958c502021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9600000000-b66c0ed4c5a2ec64853d2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-b463cbf4ba16bde190ec2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-138b8c24fd394024a31a2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-138b8c24fd394024a31a2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-73515b4a2a95628c8b692021-09-24View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-9800000000-1fdcf83a0134198725e52014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureOral (9) ; Inhalation (9) ; Dermal (9)
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. (8)
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. (4)
Toxicity ValuesLD50: 316 mg/kg (Oral, Mouse) (3) LD50: 898 mg/kg (Intraperitoneal, Rat) (3) LC50: 24 g/m3 over 4 hours (Inhalation, Rat) (3)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (7)
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. (8)
Minimum Risk LevelAcute Inhalation: 2 ppm (6) Chronic Inhalation: 0.2 ppm (6) Acute Oral: 0.1 mg/kg/day (6)
Health EffectsStyrene causes nervous system depression and may be carcinogenic. Animals studies have also shown that hearing loss and liver damage may occur. (8, 9)
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. (8, 9)
TreatmentTreatment is mainly symptomatic and supportive. Respiratory assistance may be needed. (9)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB34240
PubChem Compound ID7501
ChEMBL IDNot Available
ChemSpider ID7220
KEGG IDC07083
UniProt IDNot Available
OMIM ID
ChEBI ID27452
BioCyc IDCPD-1075
CTD IDNot Available
Stitch IDStyrene
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkStyrene
References
Synthesis ReferenceNot Available
MSDST3D0271.pdf
General References
  1. 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. [18554678 ]
  2. 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. [14597173 ]
  3. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  4. USEPA (1980). Ambient Water Quality Criteria Doc: Dinitrotoluene. EPA 440/5-80-045.
  5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  6. ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  7. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  8. ATSDR - Agency for Toxic Substances and Disease Registry (2007). Toxicological Profile for styrene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  9. International Programme on Chemical Safety (IPCS) INCHEM (1996). Poison Information Monograph for Styrene. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails

Targets

1. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (2007). Toxicological Profile for styrene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]