Back to Compounds

Showing Compound protocatechuate (FDB031135)

Record Information
Version1.0
Creation date2015-05-07 21:06:27 UTC
Update date2019-11-26 03:22:09 UTC
Primary IDFDB031135
Secondary Accession Numbers
  • FDB000847
Chemical Information
FooDB Nameprotocatechuate
Description3,4-dihydroxybenzoic acid, also known as protocatechuic acid or 4-carboxy-1,2-dihydroxybenzene, belongs to hydroxybenzoic acid derivatives class of compounds. Those are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3,4-dihydroxybenzoic acid is soluble (in water) and a weakly acidic compound (based on its pKa). 3,4-dihydroxybenzoic acid can be synthesized from benzoic acid. 3,4-dihydroxybenzoic acid is also a parent compound for other transformation products, including but not limited to, methyl 3,4-dihydroxybenzoate, ethyl 3,4-dihydroxybenzoate, and 1-(3,4-dihydroxybenzoyl)-beta-D-glucopyranose. 3,4-dihydroxybenzoic acid is a mild, balsamic, and phenolic tasting compound and can be found in a number of food items such as white mustard, grape wine, abalone, and asian pear, which makes 3,4-dihydroxybenzoic acid a potential biomarker for the consumption of these food products. 3,4-dihydroxybenzoic acid can be found primarily in blood, feces, and urine, as well as in human fibroblasts and testes tissues. 3,4-dihydroxybenzoic acid exists in all eukaryotes, ranging from yeast to humans. Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in in vitro and in vivo studies .
CAS Number99-50-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
4,5-Dihydroxybenzoic acidChEBI
4-Carboxy-1,2-dihydroxybenzeneChEBI
Protocatehuic acidChEBI
3,4-Dihydroxybenzoic acidKegg
ProtocatechuateKegg
4,5-DihydroxybenzoateGenerator
ProtocatehuateGenerator
3,4-DihydroxybenzoateGenerator
Protocatechuic acid, monosodium saltHMDB
Protocatechuic acid, carboxy-14C-labeledHMDB
2,4-DihydroxybenzoateHMDB
2,4-Dihydroxybenzoic acidHMDB
b-ResorcylateHMDB
b-Resorcylic acidHMDB
beta-ResorcylateHMDB
beta-Resorcylic acidHMDB
3,4-DHBAHMDB
1,2-Dihydroxybenzene-4-carboxylic acidPhytoBank
Protocatechoic acidPhytoBank
Proto-catechuic acidPhytoBank
Protocatechuic acidHMDB
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H6O4
IUPAC name3,4-dihydroxybenzoic acid
InChI IdentifierInChI=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
Isomeric SMILESOC(=O)C1=CC(O)=C(O)C=C1
Average Molecular Weight154.121
Monoisotopic Molecular Weight154.026608673
Classification
Description Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives 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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSProtocatechuic acid, 3 TMS, GC-MS Spectrumsplash10-0006-0913000000-0933eeed3701393aa41fSpectrum
GC-MSProtocatechuic acid, non-derivatized, GC-MS Spectrumsplash10-0006-0911000000-ca1452bfe34749c0d8c1Spectrum
GC-MSProtocatechuic acid, 3 TMS, GC-MS Spectrumsplash10-00dl-9711000000-595a58baf84bb73670aeSpectrum
GC-MSProtocatechuic acid, 3 TMS, GC-MS Spectrumsplash10-0006-4912000000-a095cbdb4d3809a9b775Spectrum
GC-MSProtocatechuic acid, non-derivatized, GC-MS Spectrumsplash10-0gb9-9800000000-f08a8e55f19d388091c0Spectrum
GC-MSProtocatechuic acid, non-derivatized, GC-MS Spectrumsplash10-0006-0913000000-0933eeed3701393aa41fSpectrum
GC-MSProtocatechuic acid, non-derivatized, GC-MS Spectrumsplash10-0006-0911000000-ca1452bfe34749c0d8c1Spectrum
GC-MSProtocatechuic acid, non-derivatized, GC-MS Spectrumsplash10-00dl-9711000000-595a58baf84bb73670aeSpectrum
GC-MSProtocatechuic acid, non-derivatized, GC-MS Spectrumsplash10-0006-4912000000-a095cbdb4d3809a9b775Spectrum
GC-MSProtocatechuic acid, non-derivatized, GC-MS Spectrumsplash10-0006-0911000000-c141d09a094e57440cd4Spectrum
Predicted GC-MSProtocatechuic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-114r-2900000000-ad8c99ac8e347f2d0a02Spectrum
Predicted GC-MSProtocatechuic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05aj-4092000000-dfefa4fd6fad51de9dbcSpectrum
Predicted GC-MSProtocatechuic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProtocatechuic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-9e8a76eec66c42952ee92012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0296-9100000000-145f71b183841a31fdc82012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-9044e5839d8d0b8f8ee62012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0gb9-9800000000-f08a8e55f19d388091c02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-0900000000-58c9b8232fbc187217d42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0900000000-58c9b8232fbc187217d42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-0900000000-43a650326b83e2dfe5892017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-0900000000-61ebd9558aeeb60dda892017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6900000000-dbc2159e590d48566b2c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0900000000-e6774ca1e916f97ad70d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0900000000-0bc46bd9df728e43dc632021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-0d999db8c8012fe5222c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-7ecb0cf92a0c6bd881502021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0900000000-99ac3661fc7809f287962015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0900000000-df55ffdd340947acfac92015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc9-9500000000-201668ae66ab0379946f2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0900000000-99ac3661fc7809f287962015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0900000000-df55ffdd340947acfac92015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc9-9500000000-201668ae66ab0379946f2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-0595d63853a488b9c6cf2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0900000000-d794b62eb087aaa84f942015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9700000000-32a6fa42639cb300cdc92015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-0595d63853a488b9c6cf2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0900000000-d794b62eb087aaa84f942015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9700000000-32a6fa42639cb300cdc92015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference