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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-02-21 08:21:58 UTC
Update Date2018-04-16 16:59:22 UTC
HMDB IDHMDB0001856
Secondary Accession Numbers
  • HMDB01856
Metabolite Identification
Common NameProtocatechuic acid
DescriptionProtocatechuic acid (3,4-dihydroxybenzoic acid) is a natural phenolic compound found in many edible and medicinal plants. Recent studies indicate that it could be used as a protective agent against cardiovascular diseases and neoplasms. The mechanism of its action is mostly associated with antioxidant activity, including inhibition of generation as well as scavenging of free radicals and up-regulating enzymes which participate in their neutralization. (PMID 16407799 ).
Structure
Thumb
Synonyms
ValueSource
4,5-Dihydroxybenzoic acidChEBI
4-Carboxy-1,2-dihydroxybenzeneChEBI
Protocatehuic acidChEBI
4,5-DihydroxybenzoateGenerator
ProtocatechuateGenerator
ProtocatehuateGenerator
2,4-DihydroxybenzoateHMDB
2,4-Dihydroxybenzoic acidHMDB
3,4-DihydroxybenzoateHMDB
3,4-Dihydroxybenzoic acidHMDB
b-ResorcylateHMDB
b-Resorcylic acidHMDB
beta-ResorcylateHMDB
beta-Resorcylic acidHMDB
Protocatechuic acid, monosodium saltMeSH
Protocatechuic acid, carboxy-14C-labeledMeSH
Chemical FormulaC7H6O4
Average Molecular Weight154.121
Monoisotopic Molecular Weight154.026608673
IUPAC Name3,4-dihydroxybenzoic acid
Traditional Name3,4-dihydroxybenzoic acid
CAS Registry Number99-50-3
SMILES
OC(=O)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)
InChI KeyYQUVCSBJEUQKSH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. These are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Dihydroxybenzoic acid
  • Hydroxybenzoic acid
  • Benzoic acid
  • Benzoyl
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point221 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility18.2 mg/mL at 14 °CYALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP0.86HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility12.4 g/LALOGPS
logP1.32ALOGPS
logP1.02ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.28 m³·mol⁻¹ChemAxon
Polarizability13.85 ųChemAxon
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-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0006-0913000000-0933eeed3701393aa41fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0006-0911000000-ca1452bfe34749c0d8c1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00dl-9711000000-595a58baf84bb73670aeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0006-4912000000-a095cbdb4d3809a9b775View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gb9-9800000000-f08a8e55f19d388091c0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0913000000-0933eeed3701393aa41fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0911000000-ca1452bfe34749c0d8c1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dl-9711000000-595a58baf84bb73670aeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-4912000000-a095cbdb4d3809a9b775View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0911000000-c141d09a094e57440cd4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-114r-2900000000-ad8c99ac8e347f2d0a02View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-05aj-4092000000-dfefa4fd6fad51de9dbcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-9e8a76eec66c42952ee9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0296-9100000000-145f71b183841a31fdc8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-9044e5839d8d0b8f8ee6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0gb9-9800000000-f08a8e55f19d388091c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-0900000000-58c9b8232fbc187217d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0900000000-58c9b8232fbc187217d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-0900000000-43a650326b83e2dfe589View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-0900000000-61ebd9558aeeb60dda89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0900000000-99ac3661fc7809f28796View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0900000000-df55ffdd340947acfac9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc9-9500000000-201668ae66ab0379946fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0900000000-99ac3661fc7809f28796View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0900000000-df55ffdd340947acfac9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc9-9500000000-201668ae66ab0379946fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-0595d63853a488b9c6cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0900000000-d794b62eb087aaa84f94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9700000000-32a6fa42639cb300cdc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-0595d63853a488b9c6cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0900000000-d794b62eb087aaa84f94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9700000000-32a6fa42639cb300cdc9View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Fibroblasts
  • Testes
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.49 +/- 0.062 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.226 +/- 0.044 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.224 +/- 0.036 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.231 +/- 0.037 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.267 +/- 0.046 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.253 +/- 0.039 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.239 +/- 0.044 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.2 +/- 0.034 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified1.232 +/- 1.033 uMAdult (>18 years old)Male
Normal
details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 412 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 412 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 412 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 412 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 412 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 412 details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Male
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Male
Normal
details
FecesDetected and Quantified5.126 +/- 3.0496 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified6.424 +/- 7.786 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified7.397 +/- 11.420 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified8.111 +/- 6.683 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.973 (0.0130-6.0148) nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)FemaleNormal details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
UrineDetected and Quantified0.229 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0330-1.110 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.048 +/- 0.008 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.07 +/- 0.012 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.037 +/- 0.003 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 412 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 412 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 412 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 412 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 412 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 412 details
UrineDetected but not Quantified Not AvailableNot AvailableNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03946
Phenol Explorer Compound ID412
FoodDB IDFDB000847
KNApSAcK IDC00002668
Chemspider ID71
KEGG Compound IDC00230
BioCyc ID3-4-DIHYDROXYBENZOATE
BiGG IDNot Available
Wikipedia LinkProtocatechuic_acid
METLIN ID6350
PubChem Compound72
PDB IDDHB
ChEBI ID36062
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kristinsson J, Snorradottir I, Johannsson M: The metabolism of mebeverine in man: identification of urinary metabolites by gas chromatography/mass spectrometry. Pharmacol Toxicol. 1994 Mar;74(3):174-80. [PubMed:8008724 ]
  2. Liu KS, Tsao SM, Yin MC: In vitro antibacterial activity of roselle calyx and protocatechuic acid. Phytother Res. 2005 Nov;19(11):942-5. [PubMed:16317650 ]
  3. Ali BH, Al Wabel N, Blunden G: Phytochemical, pharmacological and toxicological aspects of Hibiscus sabdariffa L.: a review. Phytother Res. 2005 May;19(5):369-75. [PubMed:16106391 ]
  4. Petersen JR, Bissell MG, Mohammad AA: Laser induced resonance energy transfer--a novel approach towards achieving high sensitivity in capillary electrophoresis. I. Clinical diagnostic application. J Chromatogr A. 1996 Sep 13;744(1-2):37-44. [PubMed:8843662 ]
  5. Babich H, Sedletcaia A, Kenigsberg B: In vitro cytotoxicity of protocatechuic acid to cultured human cells from oral tissue: involvement in oxidative stress. Pharmacol Toxicol. 2002 Nov;91(5):245-53. [PubMed:12570031 ]
  6. Szumilo J: [Protocatechuic acid in cancer prevention]. Postepy Hig Med Dosw (Online). 2005;59:608-15. [PubMed:16407799 ]

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
Protocatechuic acid → Vanillic 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
Protocatechuic acid → 6-(5-carboxy-2-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Protocatechuic acid → 6-(4-carboxy-2-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Protocatechuic acid → 6-(3,4-dihydroxybenzoyloxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
Reactions
Protocatechuic acid → 2-{[(3,4-dihydroxyphenyl)(hydroxy)methylidene]amino}acetic 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
Protocatechuic acid → 4-hydroxy-3-(sulfooxy)benzoic aciddetails