Cannabis Compound Database: Showing Compound Card for Benzene (CDB000735)

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Record Information

Version

1.0

Created at

2020-03-19 00:53:53 UTC

Updated at

2020-12-07 19:07:44 UTC

CannabisDB ID

CDB000735

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Benzene

Description

Benzene 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
[6]Annulene	ChEBI
Benzen	ChEBI
Benzine	ChEBI
Benzol	ChEBI
Benzole	ChEBI
Bicarburet OF hydrogen	ChEBI
Coal naphtha	ChEBI
Cyclohexatriene	ChEBI
Mineral naphtha	ChEBI
Phene	ChEBI
Phenyl hydride	ChEBI
Pyrobenzol	ChEBI
Pyrobenzole	ChEBI
(6)Annulene	HMDB
Annulene	HMDB
Aromatic alkane	HMDB
Benzeen	HMDB
Benzin	HMDB
Benzinum	HMDB
Benzol 90	HMDB
Benzolene	HMDB
Benzolo	HMDB
Benzolum	HMDB
BNZ	HMDB
Carbon oil	HMDB
Fenzen	HMDB
Motor benzol	HMDB
Polystream	HMDB
RNG	HMDB
{[6]annulene}	HMDB

Chemical Formula

C₆H₆

Average Molecular Weight

78.11

Monoisotopic Molecular Weight

78.047

IUPAC Name

benzene

Traditional Name

benzene

CAS Registry Number

71-43-2

SMILES

C1=CC=CC=C1

InChI Identifier

InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H

InChI Key

UHOVQNZJYSORNB-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Aromatic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzenes (CHEBI:16716 )
aromatic annulene (CHEBI:16716 )
an aromatic compound (BENZENE )

Ontology

Blood and lymphatic system disorders:

Anemia

Psychiatric disorders:

Confusion

Cancer:

Gastrointestinal disorders:

Vomiting

Disposition

Source:

Food

Environmental:

Tobacco smoke

Biological:

Plant:

Fabaceae

Route of exposure:

Enteral:

Ingestion

Parenteral:

Inhalation

Biological location:

Biofluid and excreta:

Organ and components:

Role

Indirect biological role:

Carcinogen

Environmental role:

Industrial application:

Food and nutrition

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	5.5 °C	Not Available
Boiling Point	80.1 °C	Wikipedia
Water Solubility	1.79 mg/mL	Not Available
logP	2.13	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	2.03	ALOGPS
logP	1.97	ChemAxon
logS	-1.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	26.06 m³·mol⁻¹	ChemAxon
Polarizability	8.89 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-004i-9000000000-08f396d6cb4660e57caa	2014-09-20	View Spectrum
GC-MS	Benzene, non-derivatized, GC-MS Spectrum	splash10-004i-9000000000-70967112fec69784847c	Spectrum
GC-MS	Benzene, non-derivatized, GC-MS Spectrum	splash10-004i-9000000000-92ccc664b07cb6c56de9	Spectrum
GC-MS	Benzene, non-derivatized, GC-MS Spectrum	splash10-0fb9-9000000000-2aae37aac9f2a02d5e8b	Spectrum
GC-MS	Benzene, non-derivatized, GC-MS Spectrum	splash10-004i-9100000000-11f8463e7c6286637b1b	Spectrum
GC-MS	Benzene, non-derivatized, GC-MS Spectrum	splash10-004i-9000000000-70967112fec69784847c	Spectrum
GC-MS	Benzene, non-derivatized, GC-MS Spectrum	splash10-004i-9000000000-92ccc664b07cb6c56de9	Spectrum
GC-MS	Benzene, non-derivatized, GC-MS Spectrum	splash10-0fb9-9000000000-2aae37aac9f2a02d5e8b	Spectrum
GC-MS	Benzene, non-derivatized, GC-MS Spectrum	splash10-004i-9100000000-11f8463e7c6286637b1b	Spectrum
Predicted GC-MS	Benzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-9000000000-c5901591488019f3ac5d	Spectrum
Predicted GC-MS	Benzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-004i-9000000000-70967112fec69784847c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-004i-9000000000-92ccc664b07cb6c56de9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HP 5970) , Positive	splash10-0fb9-9000000000-2aae37aac9f2a02d5e8b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - CI-B (FINNIGAN-MAT 4500) , Positive	splash10-004i-9100000000-11f8463e7c6286637b1b	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-45ac36cbb443a00d6a17	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9000000000-9cad19d98e6420c7b6a3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-2dace4807cb04a7942de	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-b9df9bb9660e1fc49a7f	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-b9df9bb9660e1fc49a7f	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-b4ff542394722302be43	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-fc58e0949de9ca4842ff	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-fc58e0949de9ca4842ff	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-fc58e0949de9ca4842ff	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-b961755486c61c33c1c7	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fb9-9000000000-9a8a4f7775597a0e167e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-fd85b2b474c37c371a5a	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001505

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzene

METLIN ID

6285

PubChem Compound

241

PDB ID

Not Available

ChEBI ID

16716

References

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Showing Compound Card for Benzene (CDB000735)

Structure for CDB000735 (Benzene)