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Protocatechuic acid (FDB000847)

Record Information
Version1.0
Creation date2010-04-08 22:04:44 UTC
Update date2019-08-01 18:42:23 UTC
Primary IDFDB000847
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProtocatechuic acid
DescriptionProtocatechuic acid, also known as protocatechuate or 3,4-dihydroxybenzoate, 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. Protocatechuic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Protocatechuic acid has been detected, but not quantified in, several different foods, such as cornmints, ceylon cinnamons, macadamia nuts, spelts, and lingonberries. This could make protocatechuic acid a potential biomarker for the consumption of these foods.
CAS Number99-50-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted PropertiesNot Available
Chemical FormulaC7H6O4
IUPAC name
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
Foods
  • Cocoa and cocoa products

    • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties
    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
    EI-MS/GC-MSNot Available
    MS/MSNot Available
    NMRNot Available
    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
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    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.