CHEBI:18135 - catechol

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name catechol
ChEBI ID CHEBI:18135
Definition A benzenediol comprising of a benzene core carrying two hydroxy substituents ortho to each other.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41441, CHEBI:135158, CHEBI:3467, CHEBI:13950, CHEBI:23054
Supplier Information No supplier information found for this compound.
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Catechol ( or ), also known as pyrocatechol or 1,2-dihydroxybenzene, is an organic compound with the molecular formula C6H4(OH)2. It is the ortho isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It was first discovered by destructive distillation of the plant extract catechin. About 20,000 tonnes of catechol are now synthetically produced annually as a commodity organic chemical, mainly as a precursor to pesticides, flavors, and fragrances. Small amounts of catechol occur in fruits and vegetables.
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Formula C6H6O2
Net Charge 0
Average Mass 110.11064
Monoisotopic Mass 110.03678
InChI InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H
InChIKey YCIMNLLNPGFGHC-UHFFFAOYSA-N
SMILES Oc1ccccc1O
Roles Classification
Biological Role(s): genotoxin
A role played by a chemical compound to induce direct or indirect DNA damage. Such damage can potentially lead to the formation of a malignant tumour, but DNA damage does not lead inevitably to the creation of cancerous cells.
allelochemical
A class of secondary metabolites developed by many plants to influence the behaviour, growth or survival of herbivores, and thus acting as a defence against herbivory.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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ChEBI Ontology
Outgoing catechol (CHEBI:18135) has role allelochemical (CHEBI:62215)
catechol (CHEBI:18135) has role genotoxin (CHEBI:50902)
catechol (CHEBI:18135) has role plant metabolite (CHEBI:76924)
catechol (CHEBI:18135) is a catechols (CHEBI:33566)
catechol (CHEBI:18135) is conjugate acid of catecholate(1−) (CHEBI:50524)
Incoming 2-ethoxyphenol (CHEBI:141701) has functional parent catechol (CHEBI:18135)
2-isopropoxy-4-propenylphenol (CHEBI:59086) has functional parent catechol (CHEBI:18135)
4-allyl-2-isopropoxyphenol (CHEBI:59075) has functional parent catechol (CHEBI:18135)
4-vinylguaiacol sulfate (CHEBI:133544) has functional parent catechol (CHEBI:18135)
catechol β-D-glucuronide (CHEBI:133689) has functional parent catechol (CHEBI:18135)
guaiacol (CHEBI:28591) has functional parent catechol (CHEBI:18135)
guaiacol sulfate (CHEBI:133460) has functional parent catechol (CHEBI:18135)
pyrocatechol sulfate (CHEBI:68505) has functional parent catechol (CHEBI:18135)
catecholate(1−) (CHEBI:50524) is conjugate base of catechol (CHEBI:18135)
IUPAC Name
benzene-1,2-diol
Synonyms Sources
1,2-Benzenediol KEGG COMPOUND
1,2-Dihydroxybenzene KEGG COMPOUND
2-hydroxyphenol ChEBI
α-hydroxyphenol ChEBI
Brenzcatechin KEGG COMPOUND
Catechol KEGG COMPOUND
catechol UniProt
o-Benzenediol KEGG COMPOUND
o-hydroxyphenol NIST Chemistry WebBook
pyrocatechin ChEBI
Pyrocatechol KEGG COMPOUND
Manual Xrefs Databases
C00002644 KNApSAcK
C00090 KEGG COMPOUND
c0097 UM-BBD
C01785 KEGG COMPOUND
C15571 KEGG COMPOUND
CAQ PDBeChem
Catechol Wikipedia
CATECHOL MetaCyc
DB02232 DrugBank
HMDB0000957 HMDB
View more database links
Registry Numbers Types Sources
120-80-9 CAS Registry Number KEGG COMPOUND
120-80-9 CAS Registry Number NIST Chemistry WebBook
120-80-9 CAS Registry Number ChemIDplus
12385-08-9 CAS Registry Number KEGG COMPOUND
2936 Gmelin Registry Number Gmelin
471401 Reaxys Registry Number Reaxys
Citations
Topal S, Kocaçalişkan I, Arslan O (2006)
Herbicidal potential of catechol as an allelochemical.
Zeitschrift fur Naturforschung. C, Journal of biosciences 61, 69-73 [PubMed:16610220]
[show Abstract]
Andersson MA, Hellman BE (2005)
Different roles of Fpg and Endo III on catechol-induced DNA damage in extended-term cultures of human lymphocytes and L5178Y mouse lymphoma cells.
Toxicology in vitro : an international journal published in association with BIBRA 19, 779-786 [PubMed:15951152]
[show Abstract]
Oikawa S, Hirosawa I, Hirakawa K, Kawanishi S (2001)
Site specificity and mechanism of oxidative DNA damage induced by carcinogenic catechol.
Carcinogenesis 22, 1239-1245 [PubMed:11470755]
[show Abstract]
Baldwin RW, Clegg JA, Curran AC, Austin EB, Khan T, Ma Y, Gunn B, Hudecz F, Byers VS, Lepoittevin JP, Price MR (1999)
Regulation of the contact sensitivity response to urushiol with anti-urushiol monoclonal antibody ALG 991.
Archives of dermatological research 291, 652-658 [PubMed:10651166]
[show Abstract]
Last Modified
07 October 2016