You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-05-22 14:17:54 UTC
Update Date2017-09-21 20:33:21 UTC
HMDB IDHMDB0002466
Secondary Accession Numbers
  • HMDB02466
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
Sodium 3-hydroxybenzoic acidMeSH
3-Hydroxybenzoic acid, copper (2+) (1:1) saltMeSH
3-Hydroxybenzoic acid, monosodium saltMeSH
Chemical FormulaC7H6O3
Average Molecular Weight138.122
Monoisotopic Molecular Weight138.031694053
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 KeyIJFXRHURBJZNAO-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
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - EI-Bsplash10-000i-9500000000-d9aa814a2f50d1d836f5View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-01b9-0490000000-8dc7d3f9d21b46e65fceView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00r6-4970000000-64e7f8ae165c16e980cbView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-01bc-2970000000-477e1a234b54225b30d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-3af4e5d6be21011f5230View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9200000000-3ab18be5287b6641a69dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-0d35a29dba0bb2378516View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-7e857f89355a610eeaffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-939e8bb535cf95146346View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000l-4900000000-81482c693c488ad8f4c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0006-9300000000-3ea8e8c9716e4cd85094View 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
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 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 Quantified Not AvailableNot Available
Normal
    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 Quantified Not SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
    UrineDetected and Quantified1,0 +/- 0.44 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.135 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.00300-2.510 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.121 +/- 0.036 umol/mmol creatinineAdult (>18 years old)Male
    Normal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    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 LinkHMDB0002466
    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. [PubMed: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. [PubMed: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. [PubMed:2708944 ]
    4. http://www.chemicalland21.com/lifescience/phar/m-HYDROXYBENZOIC%20ACID.htm [Link]