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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:39 UTC
HMDB IDHMDB00423
Secondary Accession NumbersNone
Metabolite Identification
Common Name3,4-Dihydroxyhydrocinnamic 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 ).
Structure
Thumb
Synonyms
ValueSource
3,4-Dihydroxybenzenepropanoic acidChEBI
3,4-Dihydroxyhydrocinnamic acidChEBI
3,4-Dihydroxyphenylpropionic acidChEBI
3-(3,4-Dihydroxyphenyl)propionic acidChEBI
Dihydrocaffeic acidChEBI
Hydrocaffeic acidChEBI
3,4-DihydroxybenzenepropanoateGenerator
3-(3,4-Dihydroxyphenyl)propanoateGenerator
3,4-DihydroxyhydrocinnamateGenerator
3,4-DihydroxyphenylpropionateGenerator
3-(3,4-Dihydroxyphenyl)propionateGenerator
DihydrocaffeateGenerator
HydrocaffeateGenerator
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-DihydroxybenzenepropionateHMDB
3,4-Dihydroxybenzenepropionic acidHMDB
3,4-DihydroxydihydrocinnamateHMDB
3,4-Dihydroxydihydrocinnamic acidHMDB
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Name3-(3,4-dihydroxyphenyl)propanoic acid
Traditional Namedihydrocaffeic acid
CAS Registry Number1078-61-1
SMILES
OC(=O)CCC1=CC=C(O)C(O)=C1
InChI Identifier
InChI=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 KeyInChIKey=DZAUWHJDUNRCTF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanoic acids. These 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
  • 1,2-diphenol
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point136 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility428 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.62 mg/mLALOGPS
logP1.04ALOGPS
logP1.45ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.84ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.93 m3·mol-1ChemAxon
Polarizability17.85 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-004i-0921000000-69e0a3dba4177ea9ada1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000f-0900000000-1dc54a535903f260b0b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-9100000000-74f0336af78b5918b04cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-1d433aef86dca3b39c53View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-4589cb5cf740dc1eefe5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-1900000000-bc36f01d18b6b4248472View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-6900000000-e57c83d231268edc054fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9700000000-53a68c60a48fdb8e01e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4l-9600000000-a48102a57ed6eae9a8bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-2cfd60989d2ef67b4c9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0900000000-fbaa85a997efb64c857aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0l4i-9700000000-f7bdc64c528a71696640View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-867d0860de62a4c828f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01qi-1900000000-7a274d4ecad972f6ce6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9700000000-110fe57d501253fffb52View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.029 +/- 0.01 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.017 +/- 0.004 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.038 +/- 0.009 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.034 +/- 0.008 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.016 +/- 0.005 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.022 +/- 0.007 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.018 +/- 0.006 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.121 +/- 0.107 uMAdult (>18 years old)Male
Normal
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579
  • Not Applicable
details
BloodDetected and Quantified0.066 +/- 0.04 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected and Quantified27.776 +/- 41.828 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified12.516 +/- 3.348 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified19.377 +/- 13.504 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified23.604 +/- 27.940 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
UrineDetected and Quantified15.849 +/- 5.603 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified6.861 +/- 2.937 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.27 +/- 0.079 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579
  • Not Applicable
details
UrineDetected and Quantified0.174 +/- 0.055 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.252 +/- 0.034 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.154 +/- 0.02 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified9.273 +/- 5.803 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified4.853 +/- 2.891 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
UrineDetected and Quantified6.946 +/- 5.086 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified10.117 +/- 14.922 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Hypertension (mild)
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID579
Phenol Explorer Metabolite ID579
FoodDB IDFDB008857
KNApSAcK IDC00002735
Chemspider ID308986
KEGG Compound IDC10447
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00423
Metagene LinkHMDB00423
METLIN ID5412
PubChem Compound348154
PDB IDNot Available
ChEBI ID48400
References
Synthesis ReferenceSabally Kebba; Karboune Salwa; St-Louis Richard; Kermasha Selim Lipase-catalyzed transesterification of dihydrocaffeic acid with flaxseed oil for the synthesis of phenolic lipids. Journal of biotechnology (2006), 127(1), 167-76.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Vickers S, Stuart EK, Hucker HB: Further studies on the metabolism of carbidopa, (minus)-L-alpha-hydrazino-3,4-dihydroxy-alpha-methylbenzenepropanoic acid monohydrate, in the human, Rhesus monkey, dog, and rat. J Med Chem. 1975 Feb;18(2):134-8. [804550 ]
  2. Wittemer SM, Ploch M, Windeck T, Muller SC, Drewelow B, Derendorf H, Veit M: Bioavailability and pharmacokinetics of caffeoylquinic acids and flavonoids after oral administration of Artichoke leaf extracts in humans. Phytomedicine. 2005 Jan;12(1-2):28-38. [15693705 ]
  3. Huang J, de Paulis T, May JM: Antioxidant effects of dihydrocaffeic acid in human EA.hy926 endothelial cells. J Nutr Biochem. 2004 Dec;15(12):722-9. [15607645 ]
  4. Rechner AR, Kroner C: Anthocyanins and colonic metabolites of dietary polyphenols inhibit platelet function. Thromb Res. 2005;116(4):327-34. Epub 2005 Feb 8. [16038718 ]
  5. Lekse JM, Xia L, Stark J, Morrow JD, May JM: Plant catechols prevent lipid peroxidation in human plasma and erythrocytes. Mol Cell Biochem. 2001 Oct;226(1-2):89-95. [11768243 ]