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Record Information
Version3.6
Creation Date2006-05-22 14:17:54 UTC
Update Date2016-02-11 01:05:40 UTC
HMDB IDHMDB02466
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Hydroxybenzoic acid
DescriptionProduced in the gut microflora as one of the three main metabolites formed from the catechin diet. Its use in the production of glycol benzoates for the application of plasticizer in adhesive formulations is increasing. It is also used in the manufacture of alkyd resins and drilling mud additive for crude oil recovery applications. It is used as a rubber polymerization activators and retardants.
Structure
Thumb
Synonyms
ValueSource
3-CarboxyphenolChEBI
m-Hydroxybenzoic acidChEBI
m-Salicylic acidChEBI
3-HydroxybenzoateGenerator
m-HydroxybenzoateGenerator
m-SalicylateGenerator
3-Hydroxy benzoateHMDB
3-Hydroxy benzoic acidHMDB
acido m-IdrossibenzoicoHMDB
Kyselina 3-hydroxybenzoovaHMDB
m-HbaHMDB
Meta-hydroxybenzoateHMDB
Meta-hydroxybenzoic acidHMDB
Chemical FormulaC7H6O3
Average Molecular Weight138.1207
Monoisotopic Molecular Weight138.031694058
IUPAC Name3-hydroxybenzoic acid
Traditional Name3-hydroxybenzoic acid
CAS Registry Number99-06-9
SMILES
OC(=O)C1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C7H6O3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8H,(H,9,10)
InChI KeyInChIKey=IJFXRHURBJZNAO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. These are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Hydroxybenzoic acid
  • Benzoic acid
  • Benzoyl
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point202 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.25 mg/mL at 25 °CNot Available
LogP1.50HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility10.2 mg/mLALOGPS
logP1.81ALOGPS
logP1.33ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.84ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.3 m3·mol-1ChemAxon
Polarizability12.92 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00r6-4970000000-64e7f8ae165c16e980cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-3900000000-8414bbe165f560962094View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-9400000000-65d56d101aeab33c87bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-8e8d3089786e50374c30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3900000000-09f6fef5d396e66708ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-9500000000-c48f64be4d63def93719View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-587072f8cf909dafae1eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0079-9800000000-3a33a2ce526649dfab2eView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429
  • Not Applicable
details
BloodDetected and Quantified0.119 +/- 0.023 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.103 +/- 0.015 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.149 +/- 0.024 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.194 +/- 0.056 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.09 +/- 0.01 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.089 +/- 0.006 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.089 +/- 0.008 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified1.273 +/- 1.198 uMAdult (>18 years old)Male
Normal
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
FecesDetected and Quantified4.272 +/- 4.416 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified4.561 +/- 2.317 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified6.878 +/- 3.548 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified7.530 +/- 9.774 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429
  • Not Applicable
details
UrineDetected and Quantified1,0 +/- 0.44 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.121 +/- 0.036 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 ID429
Phenol Explorer Metabolite ID429
FoodDB IDFDB010507
KNApSAcK IDNot Available
Chemspider ID7142
KEGG Compound IDC00587
BioCyc ID3-HYDROXYBENZOATE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02466
Metagene LinkHMDB02466
METLIN ID6690
PubChem Compound7420
PDB ID3HB
ChEBI ID30764
References
Synthesis ReferenceUngnade, H. E.; Henick, A. S. Preparation of m-hydroxybenzoic acid. Journal of the American Chemical Society (1942), 64 1737-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Liu JH, Smith PC: Direct analysis of salicylic acid, salicyl acyl glucuronide, salicyluric acid and gentisic acid in human plasma and urine by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Jan 12;675(1):61-70. [8634769 ]
  2. Ito S, Maruta K, Imai Y, Kato T, Ito M, Nakajima S, Fujita K, Kurahashi T: Urinary p-aminobenzoic acid determined in the pancreatic function test by liquid chromatography, with electrochemical detection. Clin Chem. 1982 Feb;28(2):323-6. [6976857 ]
  3. Dubois H, Delvoux B, Ehrhardt V, Greiling H: An enzymic assay for uric acid in serum and urine compared with HPLC. J Clin Chem Clin Biochem. 1989 Mar;27(3):151-6. [2708944 ]
  4. http://www.chemicalland21.com/lifescience/phar/m-HYDROXYBENZOIC%20ACID.htm [Link]