Record Information
Creation date2015-10-09 22:29:32 UTC
Update date2017-01-19 02:36:18 UTC
FoodComEx IDPC000259
FoodDB RecordFDB021899
Chemical Information
NameHomogentisic acid
DescriptionHomogentisic 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 Number451-13-8
(2,5-dihydroxyphenyl)-Acetic acidhmdb
2,5-Dihydroxy-a-toluic acidhmdb
2,5-Dihydroxy-alpha-toluic acidhmdb
2,5-Dihydroxy-benzeneacetic acidhmdb
2,5-Dihydroxyphenylacetic acidhmdb
Homogentisate acidhmdb
Homogentisinic acidhmdb
Melanic acidhmdb
Chemical FormulaC8H8O4
IUPAC name2-(2,5-dihydroxyphenyl)acetic acid
InChI IdentifierInChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
Isomeric SMILESOC(=O)CC1=C(O)C=CC(O)=C1
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acids
Direct Parent2(hydroxyphenyl)acetic acids
Alternative Parents
  • 2(hydroxyphenyl)acetic acid
  • Hydroquinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 1 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez
Commercial Vendors
AKSci X6953
Cayman Chemical 20045
MetaSci HMDB0000130
Tokyo Chemical Industry HMDB0000130
Toronto Research Chemicals H593400