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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:14 UTC
HMDB IDHMDB0000500
Secondary Accession Numbers
  • HMDB00500
Metabolite Identification
Common Name4-Hydroxybenzoic acid
Description4-Hydroxybenzoic acid, or p-hydroxybenzoic acid, is a phenolic derivative of benzoic acid. It a white crystalline solid that is slightly soluble in water and chloroform, but well soluble in alcohols, ether, and acetone. 4-Hydroxybenzoic acid is a microbial metabolite found in Arthrobacter, Bifidobacterium, Clostridium, Corynebacterium, Eubacterium, Escherichia coli, and Microbulbifer (PMID: 16885309 , 28393285 , 29753327 ). 4-Hydroxybenzoic acid is a metabolite formed by the gut microflora detected after the consumption of whole grain.
Structure
Data?1563860654
Synonyms
ValueSource
4-CarboxyphenolChEBI
p-HYDROXYBENZOIC ACIDChEBI
p-Salicylic acidChEBI
Hydroxybenzoic acidKegg
Hydroxybenzenecarboxylic acidKegg
p-HYDROXYBENZOateGenerator
p-SalicylateGenerator
HydroxybenzoateGenerator
HydroxybenzenecarboxylateGenerator
4-HydroxybenzoateGenerator
4-Hydroxy-benzoateHMDB
4-Hydroxy-benzoesaeureHMDB
4-Hydroxy-benzoic acidHMDB
p-CarboxyphenolHMDB
p-Hydroxy-benzoateHMDB
p-Hydroxy-benzoic acidHMDB
Paraben-acidHMDB
4-Hydroxybenzoic acid, calcium saltHMDB
4-Hydroxybenzoic acid, dilithium saltHMDB
4-Hydroxybenzoic acid, disodium saltHMDB
Para-hydroxybenzoic acidHMDB
Sodium p-hydroxybenzoate tetrahydrateHMDB
4-Hydroxybenzoic acid, copper(2+)(1:1) saltHMDB
4-Hydroxybenzoic acid, dipotassium saltHMDB
4-Hydroxybenzoic acid, monopotassium saltHMDB
4-Hydroxybenzoic acid, monosodium saltHMDB
4-Hydroxybenzoic acid, monosodium salt, 11C-labeledHMDB
Chemical FormulaC7H6O3
Average Molecular Weight138.122
Monoisotopic Molecular Weight138.031694053
IUPAC Name4-hydroxybenzoic acid
Traditional NameP-hydroxybenzoic acid
CAS Registry Number99-96-7
SMILES
OC(=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)
InChI KeyFJKROLUGYXJWQN-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-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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility5 mg/mLNot Available
LogP1.58HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility11.9 g/LALOGPS
logP1.58ALOGPS
logP1.33ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.38ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.3 m³·mol⁻¹ChemAxon
Polarizability12.94 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-01b9-0490000000-89473836b0071542185eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00xu-2890000000-dd5367ba838ccd5b29d8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9540000000-11db590137f79b7a32bfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00xu-3890000000-7e553522b6ec5c075e25JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dr-5900000000-9b1d88421f1e1ded16f9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9700000000-a9bb4b71d8b23a56ca67JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0079-6900000000-617d58eb059c1e918ca0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dr-4900000000-97bfa38b0d6bc152d470JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dr-7900000000-290af590b1fc44a86969JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01b9-0490000000-d6001fb50397705d3e0bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01b9-0490000000-89473836b0071542185eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00xu-2890000000-dd5367ba838ccd5b29d8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9540000000-11db590137f79b7a32bfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00xu-3890000000-7e553522b6ec5c075e25JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00xu-2980000000-0ba0ea7d63bd7fff3b22JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-5900000000-fcde26d72ca8445dff7eJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xu-7950000000-cc553d409cc2a872749dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000f-9400000000-9fb9f8fbd7cf90a88604JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-9000000000-f5d09d09184f72ec3bd7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9000000000-d31cea608d0764edf5d0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-00dr-5900000000-9b1d88421f1e1ded16f9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-00di-9700000000-3ac766249fee4c68b8f4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0079-6900000000-4e15a4102e0b3bc8ddceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4r-9800000000-9e7208bfb79f9cca336bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9000000000-1ed6d8123d44d126ed64JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-63a0e9c65e315bb89281JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-a8befcaa45eced4a9a51JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-26788d399f2b459abc21JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0072-6900000000-ba06f5c422d59cd10ceaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-9100000000-193fd4eb0cf324fb3abcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0006-9200000000-c834f7be13341f3e19b8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00di-0900000000-4f58e660923e896589a3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4r-9800000000-9e7208bfb79f9cca336bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-1ed6d8123d44d126ed64JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-e80d9637393e63e2d07cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-a8befcaa45eced4a9a51JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0900000000-6351b89d53d1742a1fbbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-bdd873f3d1dc0f2af556JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fu-9400000000-37262c1edda5dec21a19JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3900000000-fcd512c9827982e7c9aaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-9600000000-36013030005316a50fabJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-5efa05442f95e2900559JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-00dr-6900000000-71548845dbf99346758dJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 418 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 418 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 418 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 418 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 418 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 418 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 418 details
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    BloodDetected and Quantified2.447 +/- 0.192 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified2.423 +/- 0.19 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified2.599 +/- 0.232 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified2.73 +/- 0.226 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified2.676 +/- 0.168 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified2.387 +/- 0.158 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified2.326 +/- 0.221 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified20.885 +/- 18.445 uMAdult (>18 years old)Male
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified4.996 +/- 4.923 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified5.358 +/- 5.575 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified6.516 +/- 5.647 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified8.326 +/- 10.136 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 but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Not SpecifiedBoth
    Normal
    details
    FecesDetected and Quantified5.430 +/- 4.416 nmol/g wet fecesNot SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified1.441 (0.203-12.0690) nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified29.684 +/- 31.132 nmol/g wet fecesNot SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    SalivaDetected and Quantified30.23 +/- 31.32 uMAdult (>18 years old)BothNormal
      • Zerihun T. Dame, ...
    details
    SweatDetected but not Quantified Adult BothNormal details
    UrineDetected and Quantified1.346 +/- 1.104 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
      • Mordechai, Hien, ...
    details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 418 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 418 details
    UrineDetected and Quantified1.7 (0.9-3.0) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 418 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 418 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 418 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 418 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 418 details
    UrineDetected and Quantified0.39-0.75 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified2.751 +/- 2.414 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified1.8 (0.7-29) umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified4.66+/- 1.18 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified1.8 +/- 1.8 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.36-0.57 umol/mmol creatinineAdult (>18 years old)MaleNormal details
    UrineDetected and Quantified1.291 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.230-5.900 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified3.0 (0.1-13.5) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
    UrineDetected and Quantified1.5 (0.1-2.8) umol/mmol creatinineInfant (0-1 year old)BothNormal details
    UrineDetected and Quantified2.5 (0.7-13.7) umol/mmol creatinineChildren (1-13 years old)Both
    Normal
    details
    UrineDetected and Quantified2.6 (0.1-11.1) umol/mmol creatinineChildren (1-13 years old)Both
    Normal
    details
    UrineDetected and Quantified2.0 (0.6-4.2) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified1.717 +/- 0.196 umol/mmol creatinineAdult (>18 years old)Male
    Normal
    details
    UrineDetected and Quantified2.4(1.3-3.6) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    Cerebrospinal Fluid (CSF)Detected and Quantified0.5 +/- 0.22 uMAdult (>18 years old)Both
    Supradiaphragmatic malignancy
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    UrineDetected and Quantified2.988 +/- 2.795 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified3.158 +/- 2.557 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Gastroesophageal reflux disease
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified8.201 +/- 12.712 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Hypertension (mild)
    details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Hypertension (mild)
    details
    UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
    Associated Disorders and Diseases
    Disease References
    Supradiaphragmatic malignancy
    1. Goudas LC, Langlade A, Serrie A, Matson W, Milbury P, Thurel C, Sandouk P, Carr DB: Acute decreases in cerebrospinal fluid glutathione levels after intracerebroventricular morphine for cancer pain. Anesth Analg. 1999 Nov;89(5):1209-15. [PubMed:10553836 ]
    Colorectal cancer
    1. 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 ]
    2. 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 ]
    Eosinophilic esophagitis
    1. (). Mordechai, Hien, and David S. Wishart. .
    Associated OMIM IDs
    DrugBank IDDB04242
    Phenol Explorer Compound ID418
    FoodDB IDFDB010508
    KNApSAcK IDC00000856
    Chemspider ID132
    KEGG Compound IDC00156
    BioCyc IDNot Available
    BiGG ID34069
    Wikipedia Link4-Hydroxybenzoic_acid
    METLIN ID5486
    PubChem Compound135
    PDB IDNot Available
    ChEBI ID30763
    References
    Synthesis ReferenceIvanov, G. E.; Slavcheva, L. Preparation, properties, and applications of p-hydroxy-benzoic acid. Khimiya i Industriya (1922-1988) (1966), 38(10), 458-63.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Soni MG, Taylor SL, Greenberg NA, Burdock GA: Evaluation of the health aspects of methyl paraben: a review of the published literature. Food Chem Toxicol. 2002 Oct;40(10):1335-73. [PubMed:12387298 ]
    2. Shibusawa H, Sano Y, Yamamoto T, Kambegawa A, Ohkawa T, Satoh N, Okinaga S, Arai K: A radioimmunoassay of serum 16alpha-hydroxypregnenolone with specific antiserum. Endocrinol Jpn. 1978 Apr;25(2):185-9. [PubMed:668632 ]
    3. Wiebe LI, Mercer JR, Ryan AJ: Urinary metabolites of 3,5-di-(1-[13C]methyl-1-methylethyl)4-hydroxytoluene (BHT-13C) in man. Drug Metab Dispos. 1978 May-Jun;6(3):296-302. [PubMed:26551 ]
    4. Sakurai M, Ohsako M, Nagano M, Nakamura C, Tsuzuki O, Ichikawa M, Matsumoto Y: [Effect of human serum albumin on transport of drugs through human erythrocyte membranes]. Yakugaku Zasshi. 1996 Aug;116(8):630-8. [PubMed:8831264 ]
    5. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
    6. Soni MG, Burdock GA, Taylor SL, Greenberg NA: Safety assessment of propyl paraben: a review of the published literature. Food Chem Toxicol. 2001 Jun;39(6):513-32. [PubMed:11346481 ]
    7. Peng X, Adachi K, Chen C, Kasai H, Kanoh K, Shizuri Y, Misawa N: Discovery of a marine bacterium producing 4-hydroxybenzoate and its alkyl esters, parabens. Appl Environ Microbiol. 2006 Aug;72(8):5556-61. doi: 10.1128/AEM.00494-06. [PubMed:16885309 ]
    8. Rowland I, Gibson G, Heinken A, Scott K, Swann J, Thiele I, Tuohy K: Gut microbiota functions: metabolism of nutrients and other food components. Eur J Nutr. 2018 Feb;57(1):1-24. doi: 10.1007/s00394-017-1445-8. Epub 2017 Apr 9. [PubMed:28393285 ]
    9. Kallscheuer N, Marienhagen J: Corynebacterium glutamicum as platform for the production of hydroxybenzoic acids. Microb Cell Fact. 2018 May 12;17(1):70. doi: 10.1186/s12934-018-0923-x. [PubMed:29753327 ]
    10. 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 ]

    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
    4-Hydroxybenzoic acid → 6-(4-carboxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
    4-Hydroxybenzoic acid → 3,4,5-trihydroxy-6-(4-hydroxybenzoyloxy)oxane-2-carboxylic aciddetails
    General function:
    Involved in prenyltransferase activity
    Specific function:
    Catalyzes the prenylation of para-hydroxybenzoate (PHB) with an all-trans polyprenyl group. Mediates the second step in the final reaction sequence of coenzyme Q (CoQ) biosynthesis, which is the condensation of the polyisoprenoid side chain with PHB.
    Gene Name:
    COQ2
    Uniprot ID:
    Q96H96
    Molecular weight:
    45593.67
    Reactions
    A polyprenyl diphosphate + 4-Hydroxybenzoic acid → Pyrophosphate + a 4-hydroxy-3-polyprenylbenzoatedetails
    Geranyl-PP + 4-Hydroxybenzoic acid → 4-Hydroxy-3-polyprenylbenzoate + Pyrophosphatedetails
    All-trans-hexaprenyl diphosphate + 4-Hydroxybenzoic acid → 3-Hexaprenyl-4-hydroxybenzoic acid + Pyrophosphatedetails
    Solanesyl-PP + 4-Hydroxybenzoic acid → Pyrophosphate + Prenyl benzoatedetails
    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
    4-Hydroxybenzoic acid → 4-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
    4-Hydroxybenzoic acid → 4-hydroxybenzoic acid-4-O-sulphatedetails