Record Information
Version1.0
Creation Date2018-10-03 16:32:23 UTC
Update Date2020-06-04 19:00:34 UTC
MCDB ID BMDB0063600
Secondary Accession Numbers
  • BMDB63600
Metabolite Identification
Common Namegallic acid
DescriptionGallic acid is an organic acid, also known as 3,4,5-trihydroxybenzoic acid has the chemical formula is C6H2(OH)3CO2H. 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 (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
3,4,5-Trihydroxybenzoic acidChEBI
Pyrogallol-5-carboxylic acidChEBI
3,4,5-TrihydroxybenzoateKegg
Pyrogallol-5-carboxylateGenerator
GallateGenerator
Acid, gallicMeSH
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
3,4,5-Hydroxybenzoic acidPhytoBank
Gallic acidHMDB
Chemical FormulaC7H6O5
Average Molecular Weight170.12
Monoisotopic Molecular Weight170.021523293
IUPAC Name3,4,5-trihydroxybenzoic acid
Traditional Namegalop
CAS Registry Number149-91-7
SMILES
OC(=O)C1=CC(O)=C(O)C(O)=C1
InChI Identifier
InChI=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
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
Experimental Properties
PropertyValueReference
Melting Point258 - 265 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.9 mg/mL at 20 °CNot Available
LogP0.7HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001i-0791200000-4d3e1baed2effb0bf15b2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-053r-0491700000-68a1d17dd1d0bb6c53542014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fk9-5900000000-6b43adb858d50b520ba72017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0791200000-4d3e1baed2effb0bf15b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-053r-0491700000-68a1d17dd1d0bb6c53542017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0691200000-8b11cbd28f656c4426b42017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fmi-1900000000-56bf9b5e0a68a9c0776a2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00xu-4009300000-4326897e134d4856b1802017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0umi-0900000000-e8e6e57cdaf8d518781a2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-9600000000-8b3c3dc9e263c174a0ac2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ue9-9000000000-da4704e31ba4de6b3aca2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0fk9-5900000000-425a258abda96a507ea02012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-951aa8106825faaca3f92012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0900000000-bdedf4b4b4fd922ec7042012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-5900000000-46d7a232b169910da4622012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9300000000-010429242e38b1b28c132012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0g29-9100000000-fb4dc241b26c248950f72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0ufr-0900000000-8e1ce790677a7c04e5802017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-004i-0900000000-8999270f1e2b746047f72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-880097b21bcd57ec8f772017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-bdedf4b4b4fd922ec7042017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-5900000000-bf4cb2a480d9abb570d42017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9300000000-63bfcc112fc600a150de2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0g29-9100000000-fb4dc241b26c248950f72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-6a9289e729e66d03cf502017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-175241488c5f0956df1f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0kor-0900000000-1ceb76e12bc399878e0d2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-8e403dcee60bc20ba7b42016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-0900000000-20a78444c2179ed7730f2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00os-9800000000-3011ae50626d9c15fadd2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-bceef5d1a34c38d340ed2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-0900000000-bbec391317d064ab4d892016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-8900000000-049b564c5923498a6f3e2016-09-12View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0fk9-2900000000-1949ca7ce1b8b610c2782015-03-01View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, experimental)Not Available2015-03-01View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)Not Available2015-03-12View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.00411 +/- 0.00024 uM
  • Shin Tsen, Jinyi ...
details
Detected and Quantified0.002 +/- 0.0011 uM
  • Shin Tsen, Jinyi ...
details
Detected and Quantified0.000235 +/- 0.000235 uM
  • Shin Tsen, Jinyi ...
details
Detected and Quantified0.00411 +/- 0.00035 uM
  • Shin Tsen, Jinyi ...
details
HMDB IDHMDB0005807
DrugBank IDNot Available
Phenol Explorer Compound ID413
FoodDB IDFDB000662
KNApSAcK IDC00002647
Chemspider ID361
KEGG Compound IDC01424
BioCyc IDCPD-183
BiGG IDNot Available
Wikipedia LinkGallic_acid
METLIN ID3295
PubChem Compound370
PDB IDNot Available
ChEBI ID30778
References
Synthesis ReferenceCheng K F; Yip C S; Yeung H W; Kong Y C Leonurine, an improved synthesis. Experientia (1979), 35(5), 571-2. PubMed ID 446644
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Shin Tsen, Jinyi Siew, Eunice Lau, Farzana A qah Bte Roslee, Hui Chan, Wai Loke (2014). Shin Tsen, Jinyi Siew, Eunice Lau, Farzana A qah Bte Roslee, Hui Chan, Wai Loke Cow’s milk as a dietary source of equol and phenolic antioxidants: di erential distribution in the milk aqueous and lipid fractions. Dairy Sci. & Technol. (2014) 94:625–632. DOI 10.1007/s13594-014-0183-4. Dairy Science & Technology.