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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:09 UTC
HMDB IDHMDB0000423
Secondary Accession Numbers
  • HMDB00423
Metabolite Identification
Common Name3,4-Dihydroxyhydrocinnamic acid
Description3,4-Dihydroxyhydrocinnamic acid, also known as 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 conveys the antioxidant effect in plasma and in erythrocytes (PMID: 11768243 ). 3,4-Dihydroxyhydrocinnamic acid is a microbial metabolite found in Bifidobacterium, Escherichia, Lactobacillus, and Clostridium (PMID: 28393285 ).
Structure
Data?1563860649
Synonyms
ValueSource
3,4-Dihydroxy-beta-phenylpropionic acidChEBI
3,4-Dihydroxybenzenepropanoic acidChEBI
3,4-Dihydroxybenzenepropionic acidChEBI
3,4-Dihydroxydihydrocinnamic acidChEBI
3,4-Dihydroxyphenylpropionic acidChEBI
3-(3,4-Dihydroxyphenyl)propionic acidChEBI
Dihydrocaffeic acidChEBI
Hydrocaffeic acidChEBI
3-(3,4-Dihydroxyphenyl)propanoateKegg
3,4-Dihydroxy-b-phenylpropionateGenerator
3,4-Dihydroxy-b-phenylpropionic acidGenerator
3,4-Dihydroxy-beta-phenylpropionateGenerator
3,4-Dihydroxy-β-phenylpropionateGenerator
3,4-Dihydroxy-β-phenylpropionic acidGenerator
3,4-DihydroxybenzenepropanoateGenerator
3,4-DihydroxybenzenepropionateGenerator
3,4-DihydroxydihydrocinnamateGenerator
3,4-DihydroxyphenylpropionateGenerator
3-(3,4-Dihydroxyphenyl)propionateGenerator
DihydrocaffeateGenerator
HydrocaffeateGenerator
3-(3,4-Dihydroxyphenyl)propanoic acidGenerator
3,4-DihydroxyhydrocinnamateGenerator
3,4-Dihydroxy-(6ci,7ci,8ci)hydrocinnamateHMDB
3,4-Dihydroxy-(6ci,7ci,8ci)hydrocinnamic acidHMDB
3,4-Dihydroxyphenylpropionic acid, potassium saltHMDB
3,4-Dihydroxyhydrocinnamic acidHMDB
DHCHMDB
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(O)=C(O)C=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 KeyDZAUWHJDUNRCTF-UHFFFAOYSA-N
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.93 m³·mol⁻¹ChemAxon
Polarizability17.85 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-004i-0921000000-69e0a3dba4177ea9ada1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-0921000000-69e0a3dba4177ea9ada1JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-1900000000-8f0742a594d0db727f11JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00ur-8069000000-113cede8ffd5381ab0cbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000f-0900000000-1dc54a535903f260b0b5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-9100000000-74f0336af78b5918b04cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-1d433aef86dca3b39c53JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-4589cb5cf740dc1eefe5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-1900000000-bc36f01d18b6b4248472JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-6900000000-e57c83d231268edc054fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9700000000-53a68c60a48fdb8e01e6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4l-9600000000-a48102a57ed6eae9a8bfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-4589cb5cf740dc1eefe5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-1900000000-8a038a280dd3f89e7884JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-6900000000-2b1f1c909f6abe0d4256JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9700000000-53a68c60a48fdb8e01e6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9600000000-a48102a57ed6eae9a8bfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-2cfd60989d2ef67b4c9bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0900000000-fbaa85a997efb64c857aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0l4i-9700000000-f7bdc64c528a71696640JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-867d0860de62a4c828f0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01qi-1900000000-7a274d4ecad972f6ce6fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9700000000-110fe57d501253fffb52JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579 details
BloodDetected and Quantified0.066 +/- 0.04 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected and Quantified27.776 +/- 41.828 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified12.516 +/- 3.348 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified19.377 +/- 13.504 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified23.604 +/- 27.940 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
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 Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.27 +/- 0.079 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 579 details
UrineDetected and Quantified0.63 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0440-3.800 umol/mmol creatinineAdult (>18 years old)Both
Normal
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
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 Quantified Adult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not Quantified Adult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound ID579
FoodDB IDFDB008857
KNApSAcK IDC00002735
Chemspider ID308986
KEGG Compound IDC10447
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5412
PubChem Compound348154
PDB IDNot Available
ChEBI ID48400
Food Biomarker OntologyNot Available
VMH IDNot Available
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. [PubMed:804550 ]
  2. 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. [PubMed:15607645 ]
  3. 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. [PubMed:15693705 ]
  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. [PubMed: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. [PubMed:11768243 ]
  6. Rowland I, Gibson G, Heinken A, Scott K, Swann J, Thiele I, Tuohy K: Gut microbiota functions: metabolism of nutrients and other food components. Eur J Nutr. 2018 Feb;57(1):1-24. doi: 10.1007/s00394-017-1445-8. Epub 2017 Apr 9. [PubMed:28393285 ]
  7. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
3,4-Dihydroxyhydrocinnamic acid → Dihydroferulic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
3,4-Dihydroxyhydrocinnamic acid → 6-[5-(2-carboxyethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3,4-Dihydroxyhydrocinnamic acid → 6-[4-(2-carboxyethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3,4-Dihydroxyhydrocinnamic acid → 6-{[3-(3,4-dihydroxyphenyl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
3,4-Dihydroxyhydrocinnamic acid → Dihydrocaffeic acid 3-sulfatedetails