FComEx: Homogentisic acid (PC000259)

Record Information

Version

1.0

Creation date

2015-10-09 22:29:32 UTC

Update date

2017-01-19 02:36:18 UTC

FoodComEx ID

PC000259

FoodDB Record

FDB021899

Chemical Information

Name

Homogentisic acid

Description

Homogentisic acid, also known as homogentisate or acid, homogentisic, belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position. A dihydroxyphenylacetic acid having the two hydroxy substituents at the 2- and 5-positions. Homogentisic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Homogentisic acid exists in all living organisms, ranging from bacteria to humans. Within humans, homogentisic acid participates in a number of enzymatic reactions. In particular, homogentisic acid can be biosynthesized from 4-hydroxyphenylpyruvic acid through the action of the enzyme 4-hydroxyphenylpyruvate dioxygenase. In addition, homogentisic acid can be converted into maleylacetoacetic acid; which is mediated by the enzyme homogentisate 1,2-dioxygenase. In humans, homogentisic acid is involved in the metabolic disorder called tyrosinemia, transient, of the newborn. Outside of the human body, Homogentisic acid has been detected, but not quantified in, several different foods, such as green beans, prunus (cherry, plum), black cabbages, hyacinth beans, and gram beans. This could make homogentisic acid a potential biomarker for the consumption of these foods. Homogentisic acid is a potentially toxic compound. Homogentisic acid, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, ulcerative colitis, and crohn's disease; homogentisic acid has also been linked to the inborn metabolic disorder alkaptonuria.

CAS Number

451-13-8

Structure

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

Synonyms

Synonym	Source
(2,5-dihydroxyphenyl)-Acetate	hmdb
(2,5-dihydroxyphenyl)-Acetic acid	hmdb
2-(3,6-DIHYDROXYPHENYL)acetate	Generator
2-(3,6-DIHYDROXYPHENYL)acetIC ACID	ChEBI
2,5-Dihydroxy-a-toluate	hmdb
2,5-Dihydroxy-a-toluic acid	hmdb
2,5-Dihydroxy-alpha-toluate	hmdb
2,5-Dihydroxy-alpha-toluic acid	hmdb
2,5-Dihydroxy-benzeneacetate	hmdb
2,5-Dihydroxy-benzeneacetic acid	hmdb
2,5-Dihydroxyphenylacetate	hmdb
2,5-Dihydroxyphenylacetic acid	hmdb
Alcapton	hmdb
Homogentisate	hmdb
Homogentisate acid	hmdb
Homogentisinate	hmdb
Homogentisinic acid	hmdb
Melanic acid	hmdb

Chemical Formula

C8H8O4

IUPAC name

2-(2,5-dihydroxyphenyl)acetic acid

InChI Identifier

InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)

InChI Key

IGMNYECMUMZDDF-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CC1=C(O)C=CC(O)=C1

Average Molecular Weight

168.1467

Monoisotopic Molecular Weight

168.042258744

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylacetic acids

Direct Parent

2(hydroxyphenyl)acetic acids

Alternative Parents