Human Metabolome Database: Showing metabocard for Benzene (HMDB0001505)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-04-22 23:33:09 UTC

HMDB ID

HMDB0001505

Secondary Accession Numbers

HMDB01505

Metabolite Identification

Common Name

Benzene

Description

Benzene, also known as benzol or [6]annulene, 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. Benzene is possibly neutral. Benzene exists in all living organisms, ranging from bacteria to humans. Outside of the human body, benzene is found, on average, in the highest concentration in safflowers. benzene has also been detected, but not quantified in, a few different foods, such as common beans, guava, and lovages. This could make benzene a potential biomarker for the consumption of these foods. Benzene is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Benzene has been found to be associated with several diseases such as autism and pervasive developmental disorder not otherwise specified; also benzene has been linked to the inborn metabolic disorders including celiac disease.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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

78.1118

Monoisotopic Molecular Weight

78.046950192

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

Liquid

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	1.07 g/L	ALOGPS
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

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-70967112fec69784847c	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-92ccc664b07cb6c56de9	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fb9-9000000000-2aae37aac9f2a02d5e8b	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-004i-9100000000-11f8463e7c6286637b1b	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-70967112fec69784847c	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-92ccc664b07cb6c56de9	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fb9-9000000000-2aae37aac9f2a02d5e8b	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-004i-9100000000-11f8463e7c6286637b1b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9000000000-c5901591488019f3ac5d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-004i-9000000000-70967112fec69784847c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-004i-9000000000-92ccc664b07cb6c56de9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HP 5970) , Positive	splash10-0fb9-9000000000-2aae37aac9f2a02d5e8b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - CI-B (FINNIGAN-MAT 4500) , Positive	splash10-004i-9100000000-11f8463e7c6286637b1b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-45ac36cbb443a00d6a17	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9000000000-9cad19d98e6420c7b6a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-2dace4807cb04a7942de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-b9df9bb9660e1fc49a7f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-b9df9bb9660e1fc49a7f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-b4ff542394722302be43	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-9000000000-08f396d6cb4660e57caa	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Breath
Feces
Saliva

Tissue Locations

Bone Marrow
Epidermis
Leukocyte
Liver

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000384 (0.000320-0.000448) uM	Adult (>18 years old)	Not Specified	Normal	National Health a...	details
Blood	Detected and Quantified	0.000307 (0.000256-0.000384) uM	Children (1-13 years old)	Not Specified	Normal	National Health a...	details
Breath	Detected but not Quantified		Adult (>18 years old)	Both	Normal	24086492	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	24922509	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	17314143	details
Feces	Detected but not Quantified		Children (1-13 years old)	Both	Normal	24130822	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	19167006	details
Saliva	Detected but not Quantified		Children (1-13 years old)	Both	Normal	24657864	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Not Specified	Normal	24421258	details

Abnormal Concentrations

Biospecimen	Status	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Adult (>18 years old)	Both	Immunoglobulin A nephropathy (IgAN) non progressor	24922509	details
Feces	Detected but not Quantified	Adult (>18 years old)	Both	Immunoglobulin A nephropathy (IgAN) progressor	24922509	details
Feces	Detected but not Quantified	Children (1-13 years old)	Both	Autism	24130822	details
Feces	Detected but not Quantified	Children (1-13 years old)	Both	Pervasive Developmental Disorder Not Otherwise Specified	24130822	details
Saliva	Detected but not Quantified	Children (1-13 years old)	Both	Celiac disease	24657864	details

Associated Disorders and Diseases

Disease References

Autism
De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Celiac disease
Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]

Associated OMIM IDs

209850 (Autism)
212750 (Celiac disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012843

KNApSAcK ID

Not Available

Chemspider ID

236

KEGG Compound ID

C01407

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzene

METLIN ID

6285

PubChem Compound

241

PDB ID

Not Available

ChEBI ID

16716

Food Biomarker Ontology

Not Available

VMH ID

Not Available

References

Synthesis Reference

Copisarow, Maurice; Long, Cyril N H. The Friedel-Crafts' reaction. II. Migration of halogen atoms in the benzene nucleus. Journal of the Chemical Society, Transactions (1921), 119 442-7.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Wiwanitkit V, Soogarun S, Suwansaksri J: Urine phenol and myeloperoxidase index: an observation in benzene exposed subjects. Leuk Lymphoma. 2004 Aug;45(8):1643-5. [PubMed:15370219 ]
Wang S, Chen H, Wang X: [Studies on relationship between exposure to low concentration of mixed benzene and lower quality of semen and very early fetal loss]. Zhonghua Yu Fang Yi Xue Za Zhi. 2000 Sep;34(5):271-3. [PubMed:11372393 ]
Zhang L, Wang Y, Shang N, Smith MT: Benzene metabolites induce the loss and long arm deletion of chromosomes 5 and 7 in human lymphocytes. Leuk Res. 1998 Feb;22(2):105-13. [PubMed:9593466 ]
Fabiani R, De Bartolomeo A, Morozzi G: Involvement of oxygen free radicals in the serum-mediated increase of benzoquinone genotoxicity. Environ Mol Mutagen. 2005 Oct;46(3):156-63. [PubMed:15920754 ]
Turteltaub KW, Mani C: Benzene metabolism in rodents at doses relevant to human exposure from urban air. Res Rep Health Eff Inst. 2003 Feb;(113):1-26; discussion 27-35. [PubMed:12675491 ]
Irons RD, Stillman WS: Impact of benzene metabolites on differentiation of bone marrow progenitor cells. Environ Health Perspect. 1996 Dec;104 Suppl 6:1247-50. [PubMed:9118900 ]
Rothman N, Li GL, Dosemeci M, Bechtold WE, Marti GE, Wang YZ, Linet M, Xi LQ, Lu W, Smith MT, Titenko-Holland N, Zhang LP, Blot W, Yin SN, Hayes RB: Hematotoxicity among Chinese workers heavily exposed to benzene. Am J Ind Med. 1996 Mar;29(3):236-46. [PubMed:8833776 ]
Barbera N, Bulla G, Romano G: A fatal case of benzene poisoning. J Forensic Sci. 1998 Nov;43(6):1250-1. [PubMed:9846407 ]
Rolle-Kampczyk UE, Rehwagen M, Franck U, Weiss H, Krumbiegel P, Herbarth O: Bio-effect monitoring using a [(15)N]methacetin test as diagnostic tool to monitor remediation effects in an industrially polluted region. Toxicol Lett. 2006 Apr 10;162(2-3):234-8. Epub 2005 Oct 19. [PubMed:16242870 ]
Vermeulen R, Lan Q, Zhang L, Gunn L, McCarthy D, Woodbury RL, McGuire M, Podust VN, Li G, Chatterjee N, Mu R, Yin S, Rothman N, Smith MT: Decreased levels of CXC-chemokines in serum of benzene-exposed workers identified by array-based proteomics. Proc Natl Acad Sci U S A. 2005 Nov 22;102(47):17041-6. Epub 2005 Nov 14. [PubMed:16286641 ]
Mathews JM, De Costa KS: Absorption, metabolism, and disposition of 1,3-diphenyl-1-triazene in rats and mice after oral, i.v., and dermal administration. Drug Metab Dispos. 1999 Dec;27(12):1499-504. [PubMed:10570033 ]
Gut I, Nedelcheva V, Soucek P, Stopka P, Tichavska B: Cytochromes P450 in benzene metabolism and involvement of their metabolites and reactive oxygen species in toxicity. Environ Health Perspect. 1996 Dec;104 Suppl 6:1211-8. [PubMed:9118895 ]
Irons RD, Lv L, Gross SA, Ye X, Bao L, Wang XQ, Ryder J, Armstrong TW, Zhou Y, Miao L, Le AT, Kerzic PJ, Ni W, Fu H: Chronic exposure to benzene results in a unique form of dysplasia. Leuk Res. 2005 Dec;29(12):1371-80. Epub 2005 Sep 23. [PubMed:16183116 ]
Xiao G, Pan C, Cai Y, Lin H, Fu Z: Effect of benzene, toluene, xylene on the semen quality and the function of accessory gonad of exposed workers. Ind Health. 2001 Apr;39(2):206-10. [PubMed:11341554 ]
Dees C, Askari M, Henley D: Carcinogenic potential of benzene and toluene when evaluated using cyclin-dependent kinase activation and p53-DNA binding. Environ Health Perspect. 1996 Dec;104 Suppl 6:1289-92. [PubMed:9118908 ]
Ward E, Hornung R, Morris J, Rinsky R, Wild D, Halperin W, Guthrie W: Risk of low red or white blood cell count related to estimated benzene exposure in a rubberworker cohort (1940-1975) Am J Ind Med. 1996 Mar;29(3):247-57. [PubMed:8833777 ]
Seaton MJ, Schlosser P, Medinsky MA: In vitro conjugation of benzene metabolites by human liver: potential influence of interindividual variability on benzene toxicity. Carcinogenesis. 1995 Jul;16(7):1519-27. [PubMed:7614685 ]
Brugnone F, Perbellini L, Romeo L, Cerpelloni M, Bianchin M, Tonello A: Benzene in blood as a biomarker of low level occupational exposure. Sci Total Environ. 1999 Sep 1;235(1-3):247-52. [PubMed:10535123 ]
Ress NB: NTP Technical Report on the metabolism, toxicity and predicted carcinogenicity of diazoaminobenzene (CAS No. 136-35-6). Toxic Rep Ser. 2002 Sep;(73):1-23, A1-C6. [PubMed:12370695 ]
Surralles J, Autio K, Nylund L, Jarventaus H, Norppa H, Veidebaum T, Sorsa M, Peltonen K: Molecular cytogenetic analysis of buccal cells and lymphocytes from benzene-exposed workers. Carcinogenesis. 1997 Apr;18(4):817-23. [PubMed:9111220 ]

Showing metabocard for Benzene (HMDB0001505)

Structure for HMDB0001505 (Benzene)