catechol (CHEBI:18135)

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CHEBI:18135 - catechol

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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.

Download	Molfile XML SDF

more structures >>

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14 14 0 0 0 0 999 V2000

0.8706 -0.7194 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

0.8706 0.6937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.3537 1.3937 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.5725 0.6904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.5725 -0.7160 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.3537 -1.4193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

1.9457 -1.3732 -0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0

1.9457 1.3476 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.3679 2.4168 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4574 1.2021 -0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4574 -1.2278 -0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3679 -2.4425 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9346 -2.2547 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9346 2.2290 -0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0

6 1 4 0 0 0 0

2 1 4 0 0 0 0

7 1 1 0 0 0 0

5 6 4 0 0 0 0

4 5 4 0 0 0 0

3 4 4 0 0 0 0

2 3 4 0 0 0 0

8 2 1 0 0 0 0

3 9 1 0 0 0 0

4 10 1 0 0 0 0

5 11 1 0 0 0 0

6 12 1 0 0 0 0

7 13 1 0 0 0 0

8 14 1 0 0 0 0

M END): 29 ms

reading 14 atoms

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14 atoms created

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Molfile expand

Wikipedia	License
α-Tocopherol (alpha-tocopherol) is a type of vitamin E. Its E number is "E307". Vitamin E exists in eight different forms, four tocopherols and four tocotrienols. All feature a chromane ring, with a hydroxyl group that can donate a hydrogen atom to reduce free radicals and a hydrophobic side chain, along with an aromatic ring is situated near the carbonyls in the fatty acyl chains of the phospholipid bilayer, allows for penetration into biological membranes. It is found most in the membrane's non-raft domains, associated with omega-3 and 6 fatty acids, to partially prevent oxidation. The most prevalent form, α-tocopherol, is involved in molecular, cellular, biochemical processes closely related to overall lipoprotein and lipid homeostasis. Compared to the others, α-tocopherol is preferentially absorbed and accumulated in humans. Vitamin E is found in a variety of tissues, being lipid-soluble, and taken up by the body in a wide variety of ways. Ongoing research is believed to be "critical for manipulation of vitamin E homeostasis in a variety of oxidative stress-related disease conditions in humans." One of these disease conditions is the α-tocopherol role in the use by malaria parasites to protect themselves from the highly oxidative environment in erythrocytes. A second of these disease conditions is the α-tocopherol antioxidant properties' role cardiovascular heart disease. In preventing LDL (low-density lipoprotein) oxidation, it is able to decrease chances of atherosclerosis and arterial build-up.
Read full article at Wikipedia

Formula

C6H6O2

Net Charge

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.

View more via ChEBI Ontology

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	Types	Sources
10651166	PubMed citation	Europe PMC
11470755	PubMed citation	Europe PMC
15951152	PubMed citation	Europe PMC
16610220	PubMed citation	Europe PMC

Last Modified

07 October 2016

CHEBI:18135 - catechol

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