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Record Information
Version3.6
Creation Date2007-01-23 13:04:37 UTC
Update Date2014-06-23 20:49:58 UTC
HMDB IDHMDB05807
Secondary Accession NumbersNone
Metabolite Identification
Common NameGallic acid
DescriptionGallic 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. (Wikipedia).
Structure
Thumb
Synonyms
  1. 3,4,5-Trihydroxy-Benzoate
  2. 3,4,5-Trihydroxy-Benzoic acid
  3. 3,4,5-Trihydroxybenzoate
  4. 3,4,5-Trihydroxybenzoic acid
  5. 3,4,5-Trihydroxybenzoic acid (ACD/Name 4.0)
  6. Gallate
  7. Gallic acid
  8. Gallic acid polymer
  9. Gallic acid tech.
  10. Galop
  11. Pyrogallol-5-carboxylic acid
Chemical FormulaC7H6O5
Average Molecular Weight170.1195
Monoisotopic Molecular Weight170.021523302
IUPAC Name3,4,5-trihydroxybenzoic acid
Traditional IUPAC Namegallic acid
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
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassBenzoic Acid and Derivatives
Sub ClassHydroxybenzoic Acid Derivatives
Other Descriptors
  • Gallotannins(KEGG)
  • Hydroxybenzoic Acid Derivatives
  • trihydroxybenzoic acid(ChEBI)
Substituents
  • 1,2 Diphenol
  • Benzoyl
  • Carboxylic Acid
  • Phenol
  • Phenol Derivative
  • Pyrogallol Derivative
  • Resorcinol
Direct ParentGallic Acid and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Plant
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point258 - 265 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.9 mg/mL at 20 °CNot Available
LogP0.70HANSCH,C ET AL. (1995)
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 area97.99ChemAxon
rotatable bond count1ChemAxon
refractivity39.26ChemAxon
polarizability14.75ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.008 +/- 0.005 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.003 +/- 0.001 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.01 +/- 0.005 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.007 +/- 0.003 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.002 +/- 0 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.002 +/- 0 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.001 +/- 0 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.005 +/- 0.004 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified2.09 +/- 0.22 uMAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0533 +/- 0 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.073 +/- 0.06 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.019 +/- 0.052 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.38 +/- 0.092 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.003 +/- 0 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413
  • Not Applicable
details
UrineDetected and Quantified0.003 +/- 0.001 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.006 +/- 0.001 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID413
Phenol Explorer Metabolite ID413
FoodDB IDFDB000662
KNApSAcK IDC00002647
Chemspider ID361
KEGG Compound IDC01424
BioCyc ID1-O6-O-DIGALLOYL-BETA-D-GLUCOSE
BiGG IDNot Available
Wikipedia LinkGallic acid
NuGOwiki LinkHMDB05807
Metagene LinkHMDB05807
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 ReferencesNot Available