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
Synonyms
SynonymSource
2-Ethyl-2-propenoic acidChEBI
2-Ethylpropenoic acidChEBI
alpha-Methylene-butanoic acidChEBI
2-Ethyl-2-propenoateGenerator
2-EthylpropenoateGenerator
a-Methylene-butanoateGenerator
a-Methylene-butanoic acidGenerator
alpha-Methylene-butanoateGenerator
Α-methylene-butanoateGenerator
Α-methylene-butanoic acidGenerator
2-EthylacrylateGenerator
2-Methylene-6ci,7ci,8ci)-butyrateHMDB
2-Methylene-6ci,7ci,8ci)-butyric acidHMDB
2-MethylenebutyrateHMDB
2-Methylenebutyric acidHMDB
EthacrylateHMDB
Ethacrylic acidHMDB
Poly(2-ethylacrylic acid)HMDB
2-Ethyl acrylateHMDB
4,5-Dihydroxybenzoic acidChEBI
4-Carboxy-1,2-dihydroxybenzeneChEBI
Protocatehuic acidChEBI
4,5-DihydroxybenzoateGenerator
ProtocatechuateGenerator, KEGG
ProtocatehuateGenerator
2,4-DihydroxybenzoateHMDB
2,4-Dihydroxybenzoic acidHMDB
3,4-DihydroxybenzoateHMDB, Generator
3,4-Dihydroxybenzoic acidHMDB, KEGG
b-ResorcylateHMDB
b-Resorcylic acidHMDB
beta-ResorcylateHMDB
beta-Resorcylic acidHMDB
Protocatechuic acid, monosodium saltMeSH, HMDB
Protocatechuic acid, carboxy-14C-labeledMeSH, HMDB
3,4-DHBAHMDB
1-Hydroxy-4-methylbenzeneChEBI
4-CresolChEBI
4-HydroxytolueneChEBI
4-MethylphenolChEBI
p-KresolChEBI
p-MethylphenolChEBI
p-Tolyl alcoholChEBI
ParacresolChEBI
1-Methyl-4-hydroxybenzeneHMDB
4-(Pentafluorosulfanyl)phenolHMDB
4-Methyl phenolHMDB
4-Methyl-phenolHMDB
p-CresylateHMDB
p-Cresylic acidHMDB
p-HydroxytolueneHMDB
p-Methyl phenolHMDB
p-MethylhydroxybenzeneHMDB
p-OxytolueneHMDB
p-ToluolHMDB
Paramethyl phenolHMDB
4-Cresol, potassium saltHMDB
m-CresolHMDB
4-Cresol, aluminum saltHMDB
4-Cresol, sodium saltHMDB
Para-cresolHMDB
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
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 branched fatty acids. These are fatty acids containing a branched chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentBranched fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Unsaturated fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0006-0913000000-0933eeed3701393aa41fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0006-0911000000-ca1452bfe34749c0d8c1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00dl-9711000000-595a58baf84bb73670aeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0006-4912000000-a095cbdb4d3809a9b775JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gb9-9800000000-f08a8e55f19d388091c0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0913000000-0933eeed3701393aa41fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0911000000-ca1452bfe34749c0d8c1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dl-9711000000-595a58baf84bb73670aeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-4912000000-a095cbdb4d3809a9b775JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0911000000-c141d09a094e57440cd4JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-114r-2900000000-ad8c99ac8e347f2d0a02JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-05aj-4092000000-dfefa4fd6fad51de9dbcJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-9e8a76eec66c42952ee9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0296-9100000000-145f71b183841a31fdc8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-9044e5839d8d0b8f8ee6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0gb9-9800000000-f08a8e55f19d388091c0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-0900000000-58c9b8232fbc187217d4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0900000000-58c9b8232fbc187217d4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-0900000000-43a650326b83e2dfe589JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-0900000000-61ebd9558aeeb60dda89JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0900000000-99ac3661fc7809f28796JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0900000000-df55ffdd340947acfac9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc9-9500000000-201668ae66ab0379946fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0900000000-99ac3661fc7809f28796JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0900000000-df55ffdd340947acfac9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc9-9500000000-201668ae66ab0379946fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-0595d63853a488b9c6cfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0900000000-d794b62eb087aaa84f94JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9700000000-32a6fa42639cb300cdc9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-0595d63853a488b9c6cfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0900000000-d794b62eb087aaa84f94JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9700000000-32a6fa42639cb300cdc9JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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