Showing Compound Card for Benzene (CDB000735)

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Record Information
Version1.0
Created at2020-03-19 00:53:53 UTC
Updated at2020-12-07 19:07:44 UTC
CannabisDB IDCDB000735
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBenzene
DescriptionBenzene is a colorless, highly flammable liquid with a characteristic sweet smell. It is partially responsible for the characteristic aroma around gasoline stations. Benzene is used primarily as a precursor to the manufacture of chemicals with more complex structure, such as ethylbenzene and cumene. Benzene has a high-octane number and as a result benzene along with various aromatic derivatives like toluene and xylene typically comprise up to 25% of gasoline. Exposure to gasoline or to plant combustion products is the most frequent reason for benzene to be detected in living organisms. Outdoor air frequently contains low levels of benzene from car service stations, wood smoke, tobacco smoke, the transfer of gasoline, exhaust from motor vehicles, and industrial emissions. Low levels of benzene appear to exist and to be produced naturally in all living organisms, ranging from bacteria to plants to humans. Benzene can be produced naturally through spontaneous reactions in cells, in biofluids and in fruits or juices. In particular, benzoic acid and ascorbic acid (Vitamin C) in the presence of iron or copper ions can interact to produce benzene (PMID: 26904662 ). Benzene has been found in a number of processed foods and plants, with the highest concentration being in safflowers. Benzene has also been detected, but not quantified in other plant foods, such as common beans, guava, and lovages. Benzene is a known degradation or combustion product arising from smoking, vaping or dabbing tobacco, cannabis or cannabis oils (PMID: 28983528 ). About 50% of an individual's exposure to benzene results from smoking tobacco (or other plant products) or from exposure to tobacco smoke (PMID: 9463546 ). Smoking 40 cigarettes per day leads to the intake of about 3 milligrams (mg) of benzene (PMID: 29266361 ). This amount is about 10 times the average daily intake of benzene by nonsmokers. Typically, benzene is produced by burning wood, tobacco or cannabis at temperatures above 200 oC. It primarily arises from the degradation of high-abundance terpenes including myrcene, limonene and linalool (PMID: 28983528 ). These terpenes, when heated, initially break down into isoprene which then recombines or oxidizes to produce a variety of volatile combustion/degradation products including: methacrolein; methyl vinyl ketone; hydroxyacetone; 3-methylfuran; 2-methylnapthalene; 1,3-butadiene; 1-methylcyclohexa-1,4-diene; and benzene (PMID: 28983528 ). Benzene is frequently elevated in the breath of tobacco and cannabis smokers. Benzene is a known human carcinogen and is classified by IARC (International Agency for Research on Cancer) as a class I (most serious) carcinogen. Benzene is also a notorious cause of bone marrow failure. Substantial quantities of epidemiologic, clinical, and laboratory data link benzene to aplastic anemia, acute leukemia, bone marrow abnormalities and cardiovascular disease (PMID: 20070208 ; PMID: 24932584 ). Human exposure to benzene is a global health problem. Benzene targets the liver, kidney, lung, heart and brain and can cause DNA strand breaks and chromosomal damage.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
[6]AnnuleneChEBI
BenzenChEBI
BenzineChEBI
BenzolChEBI
BenzoleChEBI
Bicarburet OF hydrogenChEBI
Coal naphthaChEBI
CyclohexatrieneChEBI
Mineral naphthaChEBI
PheneChEBI
Phenyl hydrideChEBI
PyrobenzolChEBI
PyrobenzoleChEBI
(6)AnnuleneHMDB
AnnuleneHMDB
Aromatic alkaneHMDB
BenzeenHMDB
BenzinHMDB
BenzinumHMDB
Benzol 90HMDB
BenzoleneHMDB
BenzoloHMDB
BenzolumHMDB
BNZHMDB
Carbon oilHMDB
FenzenHMDB
Motor benzolHMDB
PolystreamHMDB
RNGHMDB
{[6]annulene}HMDB
Chemical FormulaC6H6
Average Molecular Weight78.11
Monoisotopic Molecular Weight78.047
IUPAC Namebenzene
Traditional Namebenzene
CAS Registry Number71-43-2
SMILES
C1=CC=CC=C1
InChI Identifier
InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H
InChI KeyUHOVQNZJYSORNB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Aromatic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Role

Indirect biological role:

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point5.5 °CNot Available
Boiling Point80.1 °CWikipedia
Water Solubility1.79 mg/mLNot Available
logP2.13HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP2.03ALOGPS
logP1.97ChemAxon
logS-1.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.06 m³·mol⁻¹ChemAxon
Polarizability8.89 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)splash10-004i-9000000000-08f396d6cb4660e57caa2014-09-20View Spectrum
GC-MSBenzene, non-derivatized, GC-MS Spectrumsplash10-004i-9000000000-70967112fec69784847cSpectrum
GC-MSBenzene, non-derivatized, GC-MS Spectrumsplash10-004i-9000000000-92ccc664b07cb6c56de9Spectrum
GC-MSBenzene, non-derivatized, GC-MS Spectrumsplash10-0fb9-9000000000-2aae37aac9f2a02d5e8bSpectrum
GC-MSBenzene, non-derivatized, GC-MS Spectrumsplash10-004i-9100000000-11f8463e7c6286637b1bSpectrum
GC-MSBenzene, non-derivatized, GC-MS Spectrumsplash10-004i-9000000000-70967112fec69784847cSpectrum
GC-MSBenzene, non-derivatized, GC-MS Spectrumsplash10-004i-9000000000-92ccc664b07cb6c56de9Spectrum
GC-MSBenzene, non-derivatized, GC-MS Spectrumsplash10-0fb9-9000000000-2aae37aac9f2a02d5e8bSpectrum
GC-MSBenzene, non-derivatized, GC-MS Spectrumsplash10-004i-9100000000-11f8463e7c6286637b1bSpectrum
Predicted GC-MSBenzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-9000000000-c5901591488019f3ac5dSpectrum
Predicted GC-MSBenzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-004i-9000000000-70967112fec69784847c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-004i-9000000000-92ccc664b07cb6c56de92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HP 5970) , Positivesplash10-0fb9-9000000000-2aae37aac9f2a02d5e8b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - CI-B (FINNIGAN-MAT 4500) , Positivesplash10-004i-9100000000-11f8463e7c6286637b1b2012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-45ac36cbb443a00d6a172017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-9cad19d98e6420c7b6a32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-2dace4807cb04a7942de2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-b9df9bb9660e1fc49a7f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-b9df9bb9660e1fc49a7f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-b4ff542394722302be432017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-fc58e0949de9ca4842ff2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-fc58e0949de9ca4842ff2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-fc58e0949de9ca4842ff2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-b961755486c61c33c1c72021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-9000000000-9a8a4f7775597a0e167e2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-fd85b2b474c37c371a5a2021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001505
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012843
KNApSAcK IDC00033435
Chemspider ID236
KEGG Compound IDC01407
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzene
METLIN ID6285
PubChem Compound241
PDB IDNot Available
ChEBI ID16716
References
General References
  1. Salviano Dos Santos VP, Medeiros Salgado A, Guedes Torres A, Signori Pereira K: Benzene as a Chemical Hazard in Processed Foods. Int J Food Sci. 2015;2015:545640. doi: 10.1155/2015/545640. Epub 2015 Feb 18. [PubMed:26904662 ]
  2. Meehan-Atrash J, Luo W, Strongin RM: Toxicant Formation in Dabbing: The Terpene Story. ACS Omega. 2017 Sep 30;2(9):6112-6117. doi: 10.1021/acsomega.7b01130. Epub 2017 Sep 22. [PubMed:28983528 ]
  3. Smith CJ, Livingston SD, Doolittle DJ: An international literature survey of "IARC Group I carcinogens" reported in mainstream cigarette smoke. Food Chem Toxicol. 1997 Oct-Nov;35(10-11):1107-30. doi: 10.1016/s0278-6915(97)00063-x. [PubMed:9463546 ]
  4. Fiebelkorn S, Meredith C: Estimation of the Leukemia Risk in Human Populations Exposed to Benzene from Tobacco Smoke Using Epidemiological Data. Risk Anal. 2018 Jul;38(7):1490-1501. doi: 10.1111/risa.12956. Epub 2017 Dec 19. [PubMed:29266361 ]
  5. Smith MT: Advances in understanding benzene health effects and susceptibility. Annu Rev Public Health. 2010;31:133-48 2 p following 148. doi: 10.1146/annurev.publhealth.012809.103646. [PubMed:20070208 ]
  6. Bard D, Kihal W, Schillinger C, Fermanian C, Segala C, Glorion S, Arveiler D, Weber C: Traffic-related air pollution and the onset of myocardial infarction: disclosing benzene as a trigger? A small-area case-crossover study. PLoS One. 2014 Jun 16;9(6):e100307. doi: 10.1371/journal.pone.0100307. eCollection 2014. [PubMed:24932584 ]