Vinylbenzene

Relevant Data

Food Additives Approved in the United States:

General Information

Chemical nameVinylbenzene
CAS number100-42-5
COE number11022
Flavouring typesubstances
FL No.01.015
MixtureNo
Purity of the named substance at least 95% unless otherwise specified

From webgate.ec.europa.eu

Computed Descriptors

Download SDF
2D Structure
CID7501
IUPAC Namestyrene
InChIInChI=1S/C8H8/c1-2-8-6-4-3-5-7-8/h2-7H,1H2
InChI KeyPPBRXRYQALVLMV-UHFFFAOYSA-N
Canonical SMILESC=CC1=CC=CC=C1
Molecular FormulaC8H8
Wikipediastyrene

From Pubchem

Computed Properties

Property Name Property Value
Molecular Weight104.152
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count1
Complexity68.1
CACTVS Substructure Key Fingerprint A A A D c c B w A A A A A A A A A A A A A A A A A A A A A A A A A A A w A A A A A A A A A A A B A A A A G A A A A A A A D A C A G A A w A I A A A A C A A i B C A A A C A A A g A A A I i A A A A I g I I C K A E R C A I A A g g A A I i A c A g A A O A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area0.0
Monoisotopic Mass104.063
Exact Mass104.063
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count8
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem

Food Additives Biosynthesis/Degradation

ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9691
Human Intestinal AbsorptionHIA+0.9920
Caco-2 PermeabilityCaco2+0.8961
P-glycoprotein SubstrateNon-substrate0.8077
P-glycoprotein InhibitorNon-inhibitor0.9503
Non-inhibitor0.9843
Renal Organic Cation TransporterNon-inhibitor0.8517
Distribution
Subcellular localizationLysosome0.4285
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8372
CYP450 2D6 SubstrateNon-substrate0.9158
CYP450 3A4 SubstrateNon-substrate0.8052
CYP450 1A2 InhibitorNon-inhibitor0.6715
CYP450 2C9 InhibitorNon-inhibitor0.9089
CYP450 2D6 InhibitorNon-inhibitor0.9538
CYP450 2C19 InhibitorNon-inhibitor0.8449
CYP450 3A4 InhibitorNon-inhibitor0.9332
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6502
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9197
Non-inhibitor0.9775
AMES ToxicityNon AMES toxic0.9013
CarcinogensNon-carcinogens0.5390
Fish ToxicityHigh FHMT0.9758
Tetrahymena Pyriformis ToxicityHigh TPT0.9938
Honey Bee ToxicityHigh HBT0.7987
BiodegradationNot ready biodegradable0.7103
Acute Oral ToxicityIII0.8054
Carcinogenicity (Three-class)Warning0.5426

From admetSAR

ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-2.7572LogS
Caco-2 Permeability2.1540LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.7322LD50, mol/kg
Fish Toxicity0.2054pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.1925pIGC50, ug/L

From admetSAR

Toxicity Profile

Route of ExposureOral ; Inhalation ; Dermal
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.
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.
Toxicity ValuesLD50: 316 mg/kg (Oral, Mouse) LD50: 898 mg/kg (Intraperitoneal, Rat) LC50: 24 g/m3 over 4 hours (Inhalation, Rat)
Lethal Dose
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans.
Minimum Risk LevelAcute Inhalation: 2 ppm Chronic Inhalation: 0.2 ppm Acute Oral: 0.1 mg/kg/day
Health EffectsStyrene causes nervous system depression and may be carcinogenic. Animals studies have also shown that hearing loss and liver damage may occur. (L1831, L1832)
TreatmentTreatment is mainly symptomatic and supportive. Respiratory assistance may be needed.
Reference
  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 ]

From T3DB

Taxonomic Classification

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassStyrenes
Intermediate Tree NodesNot available
Direct ParentStyrenes
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsStyrene - Aromatic hydrocarbon - Cyclic olefin - Unsaturated hydrocarbon - Olefin - Hydrocarbon - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.

From ClassyFire