Record Information
Version1.0
Creation date2010-04-08 22:04:44 UTC
Update date2018-01-23 18:46:23 UTC
Primary IDFDB000847
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProtocatechuic acid
DescriptionPresent in red wine and other plants sources. Protocatechuic acid is found in many foods, some of which are poppy, arrowhead, common salsify, and rowanberry.
CAS Number99-50-3
Structure
Thumb
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
Benzoic acid, 3,4-dihydroxy- (9CI)biospider
Carbohydroquinonic aciddb_source
Catechol-4-carboxylic aciddb_source
Hypogallic aciddb_source
Protocatechuic acidmanual
Protocatechuic acid, 8CIdb_source
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 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 54.55%; H 3.92%; O 41.52%DFC
Melting PointMp 195-196° (anhyd.)DFC
Boiling PointNot Available
Experimental Water Solubility18.2 mg/mL at 14 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP0.86HANSCH,C ET AL. (1995)
Experimental pKapKa3 1 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
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
ChemSpider ID71
ChEMBL IDCHEMBL37537
KEGG Compound IDC00230
Pubchem Compound ID72
Pubchem Substance IDNot Available
ChEBI ID36062
Phenol-Explorer ID412
DrugBank IDDB03946
HMDB IDHMDB01856
CRC / DFC (Dictionary of Food Compounds) IDBJS05-K:BJS05-K
EAFUS ID932
Dr. Duke ID3,4-DIHYDROXYBENZOIC-ACID|PROTOCATECHUIC-ACID
BIGG IDNot Available
KNApSAcK IDC00002668
HET IDDHB
Flavornet IDNot Available
GoodScent IDrw1183421
SuperScent IDNot Available
Wikipedia IDProtocatechuic_acid
Phenol-Explorer Metabolite ID412
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
alpha-glucosidase inhibitor50628 An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-glucosidase (EC 3.2.1.20).DUKE
anti aggregantDUKE
anti arrhythmic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti asthmatic49167 A drug used to treat asthma.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti clastogenDUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti ischemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti legionella33282 A substance that kills or slows the growth of bacteria.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti melanogenic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti mutagenicDUKE
anti ophidicDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti peroxidantDUKE
anti radicularDUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti sicklingDUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti tussive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
apoptoticDUKE
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
cardioprotective38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
glutathione depleting68509 A compound which causes a reduction in the levels of glutathione in cells.DUKE
hepatotoxic50908 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.DUKE
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
nephrotoxic50909 A role played by a chemical compound exihibiting itself through the ability to induce damage to the kidney in animals.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phagocytoticDUKE
prostaglandigenicDUKE
secretogogueDUKE
tyrosinase inhibitor59997 Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.DUKE
ubiquiotDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
mild
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
phenolic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsamic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.