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4-Hydroxybenzoic acid (FDB010508)

Record Information
Version1.0
Creation date2010-04-08 22:09:10 UTC
Update date2020-09-17 15:31:12 UTC
Primary IDFDB010508
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Hydroxybenzoic acid
Description4-Hydroxybenzoic acid, also known as p-hydroxybenzoate or 4-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 group. 4-Hydroxybenzoic acid is a neutral compound with a nutty and phenolic taste. 4-Hydroxybenzoic acid exists in all living species, from bacteria to humans. In humans, 4-hydroxybenzoic acid is involved in ubiquinone biosynthesis. 4-Hydroxybenzoic acid is found in highest concentrations in red huckleberries, corianders, and garden onions and in lower concentrations in soybeans, rye bread, and almonds. 4-hydroxybenzoic acid has also been detected in sour cherries, common beans, wild carrots, common oregano, and soft-necked garlics. This could make 4-hydroxybenzoic acid a potential biomarker for the consumption of these foods. 4-Hydroxybenzoic acid esters, known as parabens, are used as preservatives in cosmetics and some ophthalmic solutions. It is isomeric with 2-hydroxybenzoic acid, known as salicylic acid, a precursor to aspirin, and with 3-hydroxybenzoic acid. 4-Hydroxybenzoic acid has estrogenic activity and stimulated the growth of breast cancer cell lines (PMID: 16021681). It can be found in Escherichia coli as part of the ubiquinone pathway. In the first step of this pathway, chorismate lyase transforms chorismate into 4-hydroxybenzoate and pyruvate (PMID 1644758). In Pseudomonas sp., 4-hydroxybenzoate and chloride are produced when the enzyme 4-chlorobenzoate dehalogenase acts on the halide bond of 4-chlorobenzoate with H2O (PMID: 6497878).
CAS Number99-96-7
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H6O3
IUPAC name4-hydroxybenzoic acid
InChI IdentifierInChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)
InChI KeyFJKROLUGYXJWQN-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1=CC=C(O)C=C1
Average Molecular Weight138.122
Monoisotopic Molecular Weight138.031694053
Classification
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:

Foods
  • Cocoa and cocoa products

    • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 60.87%; H 4.38%; O 34.75%DFC
    Melting PointMp 213-214°DFC
    Boiling PointNot Available
    Experimental Water Solubility5 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
    Experimental logP1.58HANSCH,C ET AL. (1995)
    Experimental pKapKa2 9.37 (25°,50% EtOH aq.)DFC
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV Data255 () (HCl) (Berdy)DFC
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-00dr-6900000000-71548845dbf99346758d2015-03-01View Spectrum
    GC-MS4-Hydroxybenzoic acid, 2 TMS, GC-MS Spectrumsplash10-01b9-0490000000-89473836b0071542185eSpectrum
    GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00xu-2890000000-dd5367ba838ccd5b29d8Spectrum
    GC-MS4-Hydroxybenzoic acid, 2 TMS, GC-MS Spectrumsplash10-00di-9540000000-11db590137f79b7a32bfSpectrum
    GC-MS4-Hydroxybenzoic acid, 2 TMS, GC-MS Spectrumsplash10-00xu-3890000000-7e553522b6ec5c075e25Spectrum
    GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00dr-5900000000-9b1d88421f1e1ded16f9Spectrum
    GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9700000000-a9bb4b71d8b23a56ca67Spectrum
    GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0079-6900000000-617d58eb059c1e918ca0Spectrum
    GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00dr-4900000000-97bfa38b0d6bc152d470Spectrum
    GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00dr-7900000000-290af590b1fc44a86969Spectrum
    GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-01b9-0490000000-d6001fb50397705d3e0bSpectrum
    GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-01b9-0490000000-89473836b0071542185eSpectrum
    GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00xu-2890000000-dd5367ba838ccd5b29d8Spectrum
    GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9540000000-11db590137f79b7a32bfSpectrum
    GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00xu-3890000000-7e553522b6ec5c075e25Spectrum
    GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00xu-2980000000-0ba0ea7d63bd7fff3b22Spectrum
    Predicted GC-MS4-Hydroxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-5900000000-fcde26d72ca8445dff7eSpectrum
    Predicted GC-MS4-Hydroxybenzoic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00xu-7950000000-cc553d409cc2a872749dSpectrum
    Predicted GC-MS4-Hydroxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS4-Hydroxybenzoic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS4-Hydroxybenzoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS4-Hydroxybenzoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS4-Hydroxybenzoic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS4-Hydroxybenzoic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000f-9400000000-9fb9f8fbd7cf90a886042012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-9000000000-f5d09d09184f72ec3bd72012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9000000000-d31cea608d0764edf5d02012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-00dr-5900000000-9b1d88421f1e1ded16f92012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-00di-9700000000-3ac766249fee4c68b8f42012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0079-6900000000-4e15a4102e0b3bc8ddce2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4r-9800000000-9e7208bfb79f9cca336b2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9000000000-1ed6d8123d44d126ed642012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-63a0e9c65e315bb892812012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-a8befcaa45eced4a9a512012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-26788d399f2b459abc212012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0072-6900000000-ba06f5c422d59cd10cea2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-9100000000-193fd4eb0cf324fb3abc2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0006-9200000000-c834f7be13341f3e19b82012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00di-0900000000-4f58e660923e896589a32017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4r-9800000000-9e7208bfb79f9cca336b2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-1ed6d8123d44d126ed642017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-e80d9637393e63e2d07c2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-a8befcaa45eced4a9a512017-09-14View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0900000000-6351b89d53d1742a1fbb2016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-bdd873f3d1dc0f2af5562016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fu-9400000000-37262c1edda5dec21a192016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3900000000-fcd512c9827982e7c9aa2016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-9600000000-36013030005316a50fab2016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-5efa05442f95e29005592016-09-12View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, DMSO, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, DMSO, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    ChemSpider ID132
    ChEMBL IDCHEMBL441343
    KEGG Compound IDC00156
    Pubchem Compound ID135
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID418
    DrugBank IDDB04242
    HMDB IDHMDB00500
    CRC / DFC (Dictionary of Food Compounds) IDFBS67-S:FBS67-S
    EAFUS ID1726
    Dr. Duke ID4-HYDROXY-BENZOIC-ACID|P-HYDROXY-BENZOIC-ACID|HYDROXYBENZOIC-ACID
    BIGG ID34069
    KNApSAcK IDC00000856
    HET IDPHB
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDrw1040201
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite ID418
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
    anti mutagenicDUKE
    antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
    anti radicularDUKE
    anti sicklingDUKE
    cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    fungistatDUKE
    immunosuppressant35705 An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.DUKE
    pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
    phytoalexin26115 A toxin made by a plant that acts against an organism attacking it.DUKE
    prostaglandigenicDUKE
    secretogogueDUKE
    ubiquiotDUKE
    Enzymes
    NameGene NameUniProt ID
    4-hydroxybenzoate polyprenyltransferase, mitochondrialCOQ2Q96H96
    Pathways
    NameSMPDB LinkKEGG Link
    Ubiquinone BiosynthesisSMP00065 map00130
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    Flavours
    FlavorCitations
    phenolic
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    nutty
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
    — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
    — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.