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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:54 UTC
Update Date2020-02-26 21:24:10 UTC
HMDB IDHMDB0002466
Secondary Accession Numbers
  • HMDB02466
Metabolite Identification
Common Name3-Hydroxybenzoic acid
Description3-Hydroxybenzoic acid, also known as 3-hydroxybenzoate or 3-carboxyphenol, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3-Hydroxybenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Hydroxybenzoic acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 3-hydroxybenzoic acid is found, on average, in the highest concentration in american cranberries and beers. 3-hydroxybenzoic acid has also been detected, but not quantified in, a few different foods, such as bilberries, citrus, and corns. This could make 3-hydroxybenzoic acid a potential biomarker for the consumption of these foods. As well, 3-Hydroxybenzoic Acid can be found in the pineapple fruit. It can also be formed by a Pseudomonas species from 3-Chlorobenzoic acid. 3-Hydroxybenzoic acid is a monohydroxybenzoic acid.3-Hydroxybenzoic acid can be obtained by the alkali fusion of 3-sulfobenzoic acid between 210 – 220°C.3-Hydroxybenzoic acid is a component of castoreum, the exudate from the castor sacs of the mature North American beaver (Castor canadensis) and the European beaver (Castor fiber), used in perfumery.
Structure
Data?1582752250
Synonyms
ValueSource
3-CarboxyphenolChEBI
m-Hydroxybenzoic acidChEBI
m-Salicylic acidChEBI
m-HydroxybenzoateGenerator
m-SalicylateGenerator
3-HydroxybenzoateGenerator
3-Hydroxybenzoic acid, monosodium saltHMDB
Sodium 3-hydroxybenzoic acidHMDB
3-Hydroxybenzoic acid, copper (2+) (1:1) saltHMDB
3-Hydroxy benzoateHMDB
3-Hydroxy benzoic acidHMDB
Acido m-idrossibenzoicoHMDB
Kyselina 3-hydroxybenzoovaHMDB
m-HbaHMDB
Meta-hydroxybenzoateHMDB
Meta-hydroxybenzoic acidHMDB
3-Hydroxybenzoic acidKEGG
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
Description belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives 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
Disposition

Route of exposure:

Biological location:

Source:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.3 m³·mol⁻¹ChemAxon
Polarizability12.92 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00r6-4970000000-64e7f8ae165c16e980cbSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9500000000-d9aa814a2f50d1d836f5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01b9-0490000000-8dc7d3f9d21b46e65fceSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00r6-4970000000-64e7f8ae165c16e980cbSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01bc-2970000000-477e1a234b54225b30d5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-6900000000-5fa59abbf3516f7f1f5dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00r6-7950000000-6f1a99dee5c832c26f1fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-3af4e5d6be21011f5230Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9200000000-3ab18be5287b6641a69dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-0d35a29dba0bb2378516Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-7e857f89355a610eeaffSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-939e8bb535cf95146346Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000l-4900000000-81482c693c488ad8f4c5Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0006-9300000000-3ea8e8c9716e4cd85094Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-3900000000-8414bbe165f560962094Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-9400000000-65d56d101aeab33c87bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-8e8d3089786e50374c30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3900000000-09f6fef5d396e66708ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-9500000000-c48f64be4d63def93719Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-587072f8cf909dafae1eSpectrum
MSMass Spectrum (Electron Ionization)splash10-0079-9800000000-3a33a2ce526649dfab2eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified4.272 +/- 4.416 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified4.561 +/- 2.317 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified6.878 +/- 3.548 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified7.530 +/- 9.774 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Not Specified
    Normal
    details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    FecesDetected and Quantified0.340 (0.0652-1.260) nmol/g wet fecesAdult (>18 years old)Both
    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
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    Associated Disorders and Diseases
    Disease References
    Colorectal cancer
    1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
    2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
    3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    Phenol Explorer Compound ID429
    FooDB IDFDB010507
    KNApSAcK IDC00040822
    Chemspider ID7142
    KEGG Compound IDC00587
    BioCyc ID3-HYDROXYBENZOATE
    BiGG IDNot Available
    Wikipedia Link3-Hydroxybenzoic_acid
    METLIN ID6690
    PubChem Compound7420
    PDB IDNot Available
    ChEBI ID30764
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    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. 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 ]
    2. 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 ]
    3. 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 ]
    4. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]
    5. http://www.chemicalland21.com/lifescience/phar/m-HYDROXYBENZOIC%20ACID.htm [Link]

    Enzymes

    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
    Gene Name:
    UGT1A1
    Uniprot ID:
    P22309
    Molecular weight:
    59590.91
    Reactions
    3-Hydroxybenzoic acid → 6-(3-carboxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
    3-Hydroxybenzoic acid → 3,4,5-trihydroxy-6-(3-hydroxybenzoyloxy)oxane-2-carboxylic aciddetails
    General function:
    Involved in glycine N-acyltransferase activity
    Specific function:
    Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
    Gene Name:
    GLYAT
    Uniprot ID:
    Q6IB77
    Molecular weight:
    18506.33
    Reactions
    3-Hydroxybenzoic acid → 3-Hydroxyhippuric aciddetails
    General function:
    sulfotransferase activity
    Specific function:
    Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
    Gene Name:
    SULT1A3
    Uniprot ID:
    P0DMM9
    Molecular weight:
    34195.96
    Reactions
    3-Hydroxybenzoic acid → 3-hydroxybenzoic acid-3-O-sulphatedetails