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Gallic acid (FDB000662)

Record Information
Version1.0
Creation date2010-04-08 22:04:39 UTC
Update date2020-09-17 15:39:19 UTC
Primary IDFDB000662
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGallic acid
DescriptionGallic acid, also known as gallate or acid, gallic, belongs to the class of organic compounds known as gallic acids. These are organic compounds that contain a 3,4,5-trihydroxybenzoic acid moiety. Gallic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Gallic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, Gallic acid is found, on average, in the highest concentration within a few different foods, such as mango, pomegranates, and cloves and in a lower concentration in red raspberries, cumins, and turnips. Gallic acid has also been detected, but not quantified in, several different foods, such as common walnuts, tarragons, gingers, fruit juices, and corns. This could make gallic acid a potential biomarker for the consumption of these foods. A trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5.
CAS Number149-91-7
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.94 g/LALOGPS
logP1.17ALOGPS
logP0.72ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.94ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.26 m³·mol⁻¹ChemAxon
Polarizability14.75 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H6O5
IUPAC name3,4,5-trihydroxybenzoic acid
InChI IdentifierInChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)
InChI KeyLNTHITQWFMADLM-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1=CC(O)=C(O)C(O)=C1
Average Molecular Weight170.12
Monoisotopic Molecular Weight170.021523293
Classification
Description Belongs to the class of organic compounds known as gallic acids. These are organic compounds that contain a 3,4,5-trihydroxybenzoic acid moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentGallic acids
Alternative Parents
Substituents
  • Gallic acid
  • Benzenetriol
  • Benzoic acid
  • Pyrogallol derivative
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Foods
  • Cocoa and cocoa products

    • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 49.42%; H 3.55%; O 47.02%DFC
    Melting PointMp 235-240° (225°)DFC
    Boiling PointNot Available
    Experimental Water Solubility11.9 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
    Experimental logP0.70HANSCH,C ET AL. (1995)
    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
    EI-MSMass Spectrum (Electron Ionization)splash10-0fk9-2900000000-1949ca7ce1b8b610c2782015-03-01View Spectrum
    GC-MSGallic acid, non-derivatized, GC-MS Spectrumsplash10-001i-0791200000-4d3e1baed2effb0bf15bSpectrum
    GC-MSGallic acid, 4 TMS, GC-MS Spectrumsplash10-053r-0491700000-68a1d17dd1d0bb6c5354Spectrum
    GC-MSGallic acid, non-derivatized, GC-MS Spectrumsplash10-0fk9-5900000000-6b43adb858d50b520ba7Spectrum
    GC-MSGallic acid, non-derivatized, GC-MS Spectrumsplash10-001i-0791200000-4d3e1baed2effb0bf15bSpectrum
    GC-MSGallic acid, non-derivatized, GC-MS Spectrumsplash10-053r-0491700000-68a1d17dd1d0bb6c5354Spectrum
    GC-MSGallic acid, non-derivatized, GC-MS Spectrumsplash10-001i-0691200000-8b11cbd28f656c4426b4Spectrum
    Predicted GC-MSGallic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fmi-1900000000-56bf9b5e0a68a9c0776aSpectrum
    Predicted GC-MSGallic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00xu-4009300000-4326897e134d4856b180Spectrum
    Predicted GC-MSGallic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSGallic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0umi-0900000000-e8e6e57cdaf8d518781a2012-07-25View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-9600000000-8b3c3dc9e263c174a0ac2012-07-25View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ue9-9000000000-da4704e31ba4de6b3aca2012-07-25View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0fk9-5900000000-425a258abda96a507ea02012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-951aa8106825faaca3f92012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0900000000-bdedf4b4b4fd922ec7042012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-5900000000-46d7a232b169910da4622012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9300000000-010429242e38b1b28c132012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0g29-9100000000-fb4dc241b26c248950f72012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0ufr-0900000000-8e1ce790677a7c04e5802017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-004i-0900000000-8999270f1e2b746047f72017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-880097b21bcd57ec8f772017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-bdedf4b4b4fd922ec7042017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-5900000000-bf4cb2a480d9abb570d42017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9300000000-63bfcc112fc600a150de2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0g29-9100000000-fb4dc241b26c248950f72017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-6a9289e729e66d03cf502017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-175241488c5f0956df1f2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - , positivesplash10-0kor-0900000000-1ceb76e12bc399878e0d2017-09-14View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-8e403dcee60bc20ba7b42016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-0900000000-20a78444c2179ed7730f2016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00os-9800000000-3011ae50626d9c15fadd2016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-bceef5d1a34c38d340ed2016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-0900000000-bbec391317d064ab4d892016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-8900000000-049b564c5923498a6f3e2016-09-12View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    ChemSpider ID361
    ChEMBL IDCHEMBL288114
    KEGG Compound IDC01424
    Pubchem Compound ID370
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID413
    DrugBank IDNot Available
    HMDB IDHMDB05807
    CRC / DFC (Dictionary of Food Compounds) IDBFL35-I:BFL35-I
    EAFUS IDNot Available
    Dr. Duke IDGALLIC-ACID
    BIGG IDNot Available
    KNApSAcK IDC00002647
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDGallic_acid
    Phenol-Explorer Metabolite ID413
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    angiotensin converting enzyme inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
    analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
    anti adenovirus22587 A substance that destroys or inhibits replication of viruses.DUKE
    anti allergenic50857 A drug used to treat allergic reactions.DUKE
    anti anaphylactic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti angiogenic48422 An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.DUKE
    anti asthmatic49167 A drug used to treat asthma.DUKE
    anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
    anti bronchitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti carcinomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti escherichicDUKE
    anti fibrinolyticDUKE
    anti flu22587 A substance that destroys or inhibits replication of viruses.DUKE
    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 HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
    anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
    anti leishmanic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
    anti methicillin-resistant Staphylococcus aureus33282 A substance that kills or slows the growth of bacteria.DUKE
    anti mutagenicDUKE
    anti nitrosaminicDUKE
    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 periodontiticDUKE
    anti peroxidantDUKE
    anti polio22587 A substance that destroys or inhibits replication of viruses.DUKE
    anti proteolyticDUKE
    anti radicularDUKE
    anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
    anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
    antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
    apoptoticDUKE
    astringent74783 A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.DUKE
    bacteristat33282 A substance that kills or slows the growth of bacteria.DUKE
    bronchodilator35523 An agent that causes an increase in the expansion of a bronchus or bronchial tubes.DUKE
    cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    candidicideDUKE
    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
    cholereticDUKE
    cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
    cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
    floral inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
    Gram(+)icide33282 A substance that kills or slows the growth of bacteria.DUKE
    Gram(-)icide33282 A substance that kills or slows the growth of bacteria.DUKE
    hemostatDUKE
    hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
    immunomodulator50846 Biologically active substance whose activity affects or plays a role in the functioning of the immune system.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
    immunosuppressant35705 An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.DUKE
    insulin-sparingDUKE
    myorelaxantDUKE
    nephrotoxic50909 A role played by a chemical compound exihibiting itself through the ability to induce damage to the kidney in animals.DUKE
    nitric-oxide inhibitor35222 A substance that diminishes the rate of a chemical reaction.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
    stypticDUKE
    topoisomerase-I inhibitor50276 A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.DUKE
    xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).DUKE
    cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.CHEBI
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    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.