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3-(3,4-Dihydroxyphenyl)propanoic acid (PC000389)

Record Information
Version1.0
Creation date2015-10-09 22:30:24 UTC
Update date2017-01-19 02:36:21 UTC
FoodComEx IDPC000389
FoodDB RecordFDB008857
Chemical Information
Name3-(3,4-Dihydroxyphenyl)propanoic acid
Description3,4-Dihydroxyhydrocinnamic acid (or Dihydrocaffeic acid, DHCA) is a metabolite product of the hydrogenation of caffeoylquinic acids, occurring in normal human biofluids, with potent antioxidant properties. DHCA has been detected in human plasma following coffee ingestion (PMID 15607645), and is increased with some dietary sources, such as after ingestion of phenolic constituents of artichoke leaf extract. (PMID 15693705) Polyphenol-rich foods such as vegetables and fruits have been shown to significantly improve platelet function in ex vivo studies in humans. (PMID 16038718) Its antioxidant activity has been tested to reduce ferric iron in the ferric reducing antioxidant power (FRAP) assay, and it has been suggested that its catechol structure convey the antioxidant effect in plasma and in erythrocytes. (PMID 11768243) [HMDB]. 3-(3,4-Dihydroxyphenyl)propanoic acid is found in red beetroot, common beet, and olive.
CAS Number1078-61-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3-(3,4-Dihydroxyphenyl)propanoateHMDB
3-(3,4-Dihydroxyphenyl)propanoic acidmanual
3-(3,4-Dihydroxyphenyl)propionatemanual
3-(3,4-Dihydroxyphenyl)propionic acidChEBI
3,4-Dihydroxy-(6ci,7ci,8ci)hydrocinnamateHMDB
3,4-Dihydroxy-(6ci,7ci,8ci)hydrocinnamic acidHMDB
3,4-Dihydroxy-b-phenylpropionateHMDB
3,4-Dihydroxy-b-phenylpropionic acidHMDB
3,4-Dihydroxy-beta-phenylpropionateHMDB
3,4-Dihydroxy-beta-phenylpropionic acidHMDB
3,4-DihydroxybenzenepropanoateGenerator
3,4-Dihydroxybenzenepropanoic acidChEBI
3,4-Dihydroxybenzenepropanoic acid, 9CIdb_source
3,4-DihydroxybenzenepropionateHMDB
3,4-Dihydroxybenzenepropionic acidHMDB
3,4-DihydroxydihydrocinnamateHMDB
3,4-Dihydroxydihydrocinnamic acidHMDB
3,4-DihydroxyhydrocinnamateGenerator
3,4-Dihydroxyhydrocinnamic acidChEBI
3,4-Dihydroxyhydrocinnamic acid, 8CIdb_source
3,4-DihydroxyphenylpropionateGenerator
3,4-Dihydroxyphenylpropionic acidmanual
DihydrocaffeateGenerator
Dihydrocaffeic acidChEBI
HydrocaffeateGenerator
Hydrocaffeic aciddb_source
Chemical FormulaC9H10O4
IUPAC name3-(3,4-dihydroxyphenyl)propanoic acid
InChI IdentifierInChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)
InChI KeyDZAUWHJDUNRCTF-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CCC1=CC=C(O)C(O)=C1
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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 3 g
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 0076AP
iChemical 1078-61-1
MetaSci HMDB0000423
Sigma-Aldrich HMDB0000423
Toronto Research Chemicals D448700