ChemFOnt: Showing chemical card for 2-Pyrocatechuic acid (CFc000000296)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:39 UTC

Chemfont ID

CFc000000296

Molecule Identification

Common Name

2-Pyrocatechuic acid

Definition

2-Pyrocatechuic acid is a normal human benzoic acid metabolite found in plasma (PMID 16351159 ), and is normally found with increased levels after consumption of many nutrients and drugs, i.e.: cranberry juice (PMID 14733499 ), aspirin ingestion. (PMID 3342084 ) It has been found associated with idiopathic oro-facial pain due to stress (oxidative stress might enhance the production of free radicals); it has been suggested that OH radicals are responsible for the production of many systemic and local tissue injury diseases which may initially manifest as pain syndrome, and 2-Pyrocatechuic acid is a biological marker for the detection and quantification of OH radicals, and patients had significantly increased circulating levels of 2-Pyrocatechuic acid after aspirin ingestion than control subjects. (PMID 7748148 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,3 DHB	ChEBI
2,3-DIHYDROXY-benzoIC ACID	ChEBI
3-Hydroxysalicylic acid	ChEBI
Catechol-3-carboxylic acid	ChEBI
DOBK	ChEBI
O-Pyrocatechuic acid	ChEBI
Pyrocatechuic acid	ChEBI
2,3-Dihydroxybenzoic acid	Kegg
2,3-DIHYDROXY-benzoate	Generator
3-Hydroxysalicylate	Generator
Catechol-3-carboxylate	Generator
O-Pyrocatechuate	Generator
Pyrocatechuate	Generator
2,3-Dihydroxybenzoate	Generator
2-Pyrocatechuate	Generator
Catecholcarboxylate	HMDB
Catecholcarboxylic acid	HMDB
DHBA	HMDB
2,3-Dihydroxy benzoic acid	MeSH, HMDB
2-Pyrocatechuic acid, sodium salt	MeSH, HMDB
Ferri-2,3-dihydroxybenzoic acid	MeSH, HMDB
1,2-Dihydroxybenzene-3-carboxylic acid	PhytoBank

Chemical Formula

C₇H₆O₄

Average Molecular Weight

154.121

Monoisotopic Molecular Weight

154.026608673

IUPAC Name

2,3-dihydroxybenzoic acid

Traditional Name

2,3-dihydroxy-benzoic acid

CAS Registry Number

303-38-8

SMILES

OC(=O)C1=C(O)C(O)=CC=C1

InChI Identifier

InChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11)

InChI Key

GLDQAMYCGOIJDV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Salicylic acids

Alternative Parents

Substituents

Salicylic acid
Benzoic acid
Benzoyl
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dihydroxybenzoic acid (CHEBI:18026 )

Functional Ontology

Physiological effect

Health effect

Nonspecific condition

Idiopathic oro-facial pain (HMDB: HMDB0000397)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 7668368)

Excreta

Biofluid or Excreta

Urine (PMID: 9212290)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000397)

Source

Exogenous

Exogenous (HMDB: HMDB0000397)

Food

Food (HMDB: HMDB0000397)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Garden tomato (FooDB: FOOD00171)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Italian sweet red pepper (FooDB: FOOD00881)

Cabbage

Broccoli (FooDB: FOOD00034)

Root vegetable

Carrot (FooDB: FOOD00245)
Root vegetables (FooDB: FOOD00873)

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

Leaf vegetable

Romaine lettuce (FooDB: FOOD00888)

Gourd

Herb and spice

Herb

Dill (FooDB: FOOD00013)
Garlic (FooDB: FOOD00008)
Turnip (FooDB: FOOD00036)

Oilseed crop

Evening primrose (FooDB: FOOD00120)

Herbs and Spices (FooDB: FOOD00866)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Fruit

Berry

American cranberry (FooDB: FOOD00192)

Pulse

Bean

Yellow wax bean (FooDB: FOOD00882)

Endogenous

Endogenous (HMDB: HMDB0000397)

Plant

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Enterobactin Biosynthesis (PathBank: SMP0122232)
2,3-Dihydroxybenzoate Biosynthesis (PathBank: SMP0121259)
Biosynthesis of Siderophore Group Nonribosomal Peptides (PathBank: SMP0121262)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000397)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.88 g/L	ALOGPS
logP	1.42	ALOGPS
logP	1.67	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.56	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.28 m³·mol⁻¹	ChemAxon
Polarizability	13.71 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon