Identification
YMDB IDYMDB01323
NameGallic acid
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
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 exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on Gallic acid.
Structure
Thumb
Synonyms
  • 3,4,5-trihydroxy-Benzoate
  • 3,4,5-trihydroxy-Benzoic acid
  • 3,4,5-Trihydroxybenzoate
  • 3,4,5-Trihydroxybenzoic acid
  • Benzoic acid, 3,4,5-trihydroxy-
  • Gallate
  • Gallic acid
  • Gallic acid polymer
  • Gallic acid tech.
  • Gallic acid, tech.
  • Galop
  • Kyselina 3,4,5-trihydroxybenzoova
  • Kyselina gallova
  • Pyrogallol-5-carboxylic acid
  • Pyrogallol-5-carboxylate
  • Acid, gallic
  • 3,4,5-Trihydroxybenzoic acid (acd/name 4.0)
  • 3,4,5-Hydroxybenzoic acid
CAS number149-91-7
WeightAverage: 170.1195
Monoisotopic: 170.021523302
InChI KeyLNTHITQWFMADLM-UHFFFAOYSA-N
InChIInChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)
IUPAC Name3,4,5-trihydroxybenzoic acid
Traditional IUPAC Namegalop
Chemical FormulaC7H6O5
SMILES[H]OC(=O)C1=C([H])C(O[H])=C(O[H])C(O[H])=C1[H]
Chemical Taxonomy
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
Physical Properties
StateSolid
Charge0
Melting point258-265 °C
Experimental Properties
PropertyValueReference
Water Solubility11.9 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP0.70 [HANSCH,C ET AL. (1995)]PhysProp
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
Biological Properties
Cellular Locations
  • extracellular
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001i-0791200000-4d3e1baed2effb0bf15bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-053r-0491700000-68a1d17dd1d0bb6c5354JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fk9-5900000000-6b43adb858d50b520ba7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0791200000-4d3e1baed2effb0bf15bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-053r-0491700000-68a1d17dd1d0bb6c5354JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0691200000-8b11cbd28f656c4426b4JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fmi-1900000000-56bf9b5e0a68a9c0776aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00xu-4009300000-4326897e134d4856b180JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0umi-0900000000-e8e6e57cdaf8d518781aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-9600000000-8b3c3dc9e263c174a0acJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ue9-9000000000-da4704e31ba4de6b3acaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0fk9-5900000000-425a258abda96a507ea0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-951aa8106825faaca3f9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0900000000-bdedf4b4b4fd922ec704JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-5900000000-46d7a232b169910da462JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9300000000-010429242e38b1b28c13JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0g29-9100000000-fb4dc241b26c248950f7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0ufr-0900000000-8e1ce790677a7c04e580JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-004i-0900000000-8999270f1e2b746047f7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-880097b21bcd57ec8f77JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-bdedf4b4b4fd922ec704JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-5900000000-bf4cb2a480d9abb570d4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9300000000-63bfcc112fc600a150deJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0g29-9100000000-fb4dc241b26c248950f7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-6a9289e729e66d03cf50JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-175241488c5f0956df1fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0kor-0900000000-1ceb76e12bc399878e0dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-8e403dcee60bc20ba7b4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-0900000000-20a78444c2179ed7730fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00os-9800000000-3011ae50626d9c15faddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-bceef5d1a34c38d340edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-0900000000-bbec391317d064ab4d89JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-8900000000-049b564c5923498a6f3eJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0fk9-2900000000-1949ca7ce1b8b610c278JSpectraViewer | MoNA
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
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Okabe, Y., Katayama, N., Iwama, M., Watanabe, H., Ohgi, K., Irie, M., Nitta, K., Kawauchi, H., Takayanagi, Y., Oyama, F., et, a. l. .. (1991). "Comparative base specificity, stability, and lectin activity of two lectins from eggs of Rana catesbeiana and R. japonica and liver ribonuclease from R. catesbeiana." J Biochem 109:786-790.1917903
Synthesis Reference:Cheng K F; Yip C S; Yeung H W; Kong Y C Leonurine, an improved synthesis. Experientia (1979), 35(5), 571-2. PubMed ID 446644
External Links:
ResourceLink
CHEBI ID30778
HMDB IDHMDB05807
Pubchem Compound ID370
Kegg IDC01424
ChemSpider ID361
FOODB IDFDB000662
WikipediaGallic_acid
BioCyc ID1-O6-O-DIGALLOYL-BETA-D-GLUCOSE