Record Information
Version1.0
Creation date2015-10-09 22:27:36 UTC
Update date2017-01-19 02:36:10 UTC
FoodComEx IDPC000034
FoodDB RecordFDB022193
Chemical Information
Name4-Hydroxyphenylpyruvic acid
Description4-Hydroxyphenylpyruvic acid (4-HPPA) is a keto acid. It is a product of the enzyme (R)-4-hydroxyphenyllactate dehydrogenase [EC 1.1.1.222] and is formed during tyrosine metabolism (KEGG). There are two isomers of HPPA, specifically 4HPPA and 3HPPA, of which 4HPPA is the most common. The enzyme 4-hydroxyphenylpyruvic acid dioxygenase (HPD) catalyzes the reaction of 4-hydroxyphenylpyruvic acid to homogentisic acid in the tyrosine catabolism pathway. A deficiency in the catalytic activity of HPD is known to lead to tyrosinemia type III, an autosomal recessive disorder characterized by elevated levels of blood tyrosine and massive excretion of tyrosine derivatives into urine. It has been shown that hawkinsinuria, an autosomal dominant disorder characterized by the excretion of 'hawkinsin,' may also be a result of HPD deficiency (PMID: 11073718). [HMDB]
CAS Number156-39-8
Structure
Thumb
Synonyms
SynonymSource
(p-hydroxyphenyl)-Pyruvatehmdb
(p-hydroxyphenyl)-Pyruvic acidhmdb
(p-Hydroxyphenyl)pyruvatehmdb
(p-Hydroxyphenyl)pyruvic acidhmdb
3-(4-HYDROXY-phenyl)pyruvateGenerator
3-(4-HYDROXY-phenyl)pyruvIC ACIDChEBI
3-(4-hydroxyphenyl)-2-oxo-propanoatehmdb
3-(4-hydroxyphenyl)-2-oxo-propanoic acidhmdb
3-(4-Hydroxyphenyl)-2-oxopropionatehmdb
3-(4-Hydroxyphenyl)-2-oxopropionic acidhmdb
3-(4-Hydroxyphenyl)pyruvatehmdb
3-(4-Hydroxyphenyl)pyruvic acidhmdb
3-(P-Hydroxyphenyl)-2-oxopropanoateGenerator
3-(P-Hydroxyphenyl)-2-oxopropanoic acidChEBI
3-(p-Hydroxyphenyl)-2-oxopropionatehmdb
3-(p-Hydroxyphenyl)-2-oxopropionic acidhmdb
3-(p-Hydroxyphenyl)pyruvatehmdb
3-(p-Hydroxyphenyl)pyruvic acidhmdb
4-Hydroxy a-oxobenzenepropanoateGenerator
4-Hydroxy a-oxobenzenepropanoic acidGenerator
4-Hydroxy alpha-oxobenzenepropanoateGenerator
4-Hydroxy alpha-oxobenzenepropanoic acidChEBI
4-Hydroxy α-oxobenzenepropanoateGenerator
4-Hydroxy α-oxobenzenepropanoic acidGenerator
4-Hydroxy-a-oxobenzenepropanoatehmdb
4-Hydroxy-a-oxobenzenepropanoic acidhmdb
4-Hydroxy-alpha-oxobenzenepropanoatehmdb
4-Hydroxy-alpha-oxobenzenepropanoic acidhmdb
4-hydroxyphenylpyruvatehmdb
4HPPAhmdb
Hydroxyphenylpyruvatehmdb
Hydroxyphenylpyruvic acidhmdb
P-HydroxyphenylpyruvateGenerator
p-hydroxyphenylpyruvichmdb
P-Hydroxyphenylpyruvic acidChEBI
Testacidhmdb
Chemical FormulaC9H8O4
IUPAC name3-hydroxy-2-oxo-3-phenylpropanoic acid
InChI IdentifierInChI=1S/C9H8O4/c10-7(8(11)9(12)13)6-4-2-1-3-5-6/h1-5,7,10H,(H,12,13)
InChI KeyZHLWCBHWYUISFY-UHFFFAOYSA-N
Isomeric SMILESOC(C(=O)C(O)=O)C1=CC=CC=C1
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpyruvic acid derivatives
Direct ParentPhenylpyruvic acid derivatives
Alternative Parents
Substituents
  • Phenylpyruvate
  • 3-phenylpropanoic-acid
  • Beta-hydroxy acid
  • Alpha-keto acid
  • Acyloin
  • Hydroxy acid
  • Keto acid
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Aromatic alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 30 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci C107
MetaSci HMDB0000707
Sigma-Aldrich HMDB0000707
Toronto Research Chemicals H949870