Record Information
Version1.0
Creation date2010-04-08 22:04:39 UTC
Update date2018-05-28 23:02:31 UTC
Primary IDFDB000662
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGallic acid
DescriptionPresent in red wine. Japan approved food antioxidant additive Gallic acid is an organic acid, also known as 3,4,5-trihydroxybenzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. The chemical formula is C6H2(OH)3CO2H. Gallic acid is found both free and as part of tannins. It is commonly used in the pharmaceutical industry. Gallic acid can also be used to synthesize the hallucinogenic alkaloid mescaline, also known as 3,4,5-trimethoxyphenethylamine.; ; Salts and esters of gallic acid are termed gallates.; ; .; Gallic acid is an organic acid, also known as 3,4,5-trihydroxybenzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. The chemical formula is C6H2(OH)3COOH. Gallic acid is found both free and as part of tannins. Salts and esters of gallic acid are termed gallates. Despite its name, it does not contain gallium.; Gallic acid was one of the substances used by Angelo Mai among other early investigators of palimpsests to clear the top layer of text off and reveal hidden manuscripts underneath. Mai was the first to employ it, but did so "with a heavy hand," often damaging manuscripts for future study.[citation needed].
CAS Number149-91-7
Structure
Thumb
Synonyms
SynonymSource
3,4,5-Trihydroxybenzoic acidChEBI
Pyrogallol-5-carboxylic acidChEBI
3,4,5-TrihydroxybenzoateKegg
Pyrogallol-5-carboxylateGenerator
GallateGenerator
3,4,5-Trihydroxy-benzoateHMDB
3,4,5-Trihydroxy-benzoic acidHMDB
3,4,5-Trihydroxybenzoic acid (acd/name 4.0)HMDB
Gallic acid polymerHMDB
Gallic acid tech.HMDB
GalopHMDB
Acid, gallicHMDB
Gallic aciddb_source
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001i-0791200000-4d3e1baed2effb0bf15bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-053r-0491700000-68a1d17dd1d0bb6c5354View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fk9-5900000000-6b43adb858d50b520ba7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0791200000-4d3e1baed2effb0bf15bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-053r-0491700000-68a1d17dd1d0bb6c5354View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0691200000-8b11cbd28f656c4426b4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fmi-1900000000-56bf9b5e0a68a9c0776aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00xu-4009300000-4326897e134d4856b180View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0umi-0900000000-e8e6e57cdaf8d518781aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-9600000000-8b3c3dc9e263c174a0acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ue9-9000000000-da4704e31ba4de6b3acaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0fk9-5900000000-425a258abda96a507ea0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-951aa8106825faaca3f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0900000000-bdedf4b4b4fd922ec704View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-5900000000-46d7a232b169910da462View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9300000000-010429242e38b1b28c13View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0g29-9100000000-fb4dc241b26c248950f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0ufr-0900000000-8e1ce790677a7c04e580View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-004i-0900000000-8999270f1e2b746047f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-880097b21bcd57ec8f77View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-bdedf4b4b4fd922ec704View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-5900000000-bf4cb2a480d9abb570d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9300000000-63bfcc112fc600a150deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0g29-9100000000-fb4dc241b26c248950f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-6a9289e729e66d03cf50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-175241488c5f0956df1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0kor-0900000000-1ceb76e12bc399878e0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-8e403dcee60bc20ba7b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-0900000000-20a78444c2179ed7730fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00os-9800000000-3011ae50626d9c15faddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-bceef5d1a34c38d340edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-0900000000-bbec391317d064ab4d89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-8900000000-049b564c5923498a6f3eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0fk9-2900000000-1949ca7ce1b8b610c278View 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 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
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.