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Showing Compound 2,4-Dihydroxybenzoic acid (FDB000842)

Record Information
Version1.0
Creation date2010-04-08 22:04:44 UTC
Update date2020-02-24 19:10:15 UTC
Primary IDFDB000842
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2,4-Dihydroxybenzoic acid
Description2,4-Dihydroxybenzoic acid 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. 2,4-Dihydroxybenzoic acid is a mild and phenolic tasting compound. 2,4-Dihydroxybenzoic acid is found, on average, in the highest concentration within american cranberries (Vaccinium macrocarpon) and olives (Olea europaea). 2,4-Dihydroxybenzoic acid has also been detected, but not quantified in, several different foods, such as alcoholic beverages, german camomiles (Matricaria recutita), fruits, coffee and coffee products, and arabica coffees (Coffea arabica). This could make 2,4-dihydroxybenzoic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2,4-Dihydroxybenzoic acid.
CAS Number89-86-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2,4-DihydroxybenzoateGenerator
24-Dihydroxybenzoic acidChEMBL, HMDB
24-Dihydroxy-benzoic acidChEMBL, HMDB
Beta-Resorcylic acidChEMBL, HMDB, MeSH
24-DihydroxybenzoateGenerator, HMDB
24-Dihydroxy-benzoateGenerator, HMDB
b-ResorcylateGenerator, HMDB
b-Resorcylic acidGenerator, HMDB
beta-ResorcylateGenerator, HMDB
β-resorcylateGenerator, HMDB
β-resorcylic acidGenerator, HMDB
2,4-DHBAHMDB
2,4-Dihydroxy-benzoic acidHMDB
4-CarboxyresorcinolHMDB
4-Hydroxysalicylic acidHMDB
b-Resorcylic acid, 8ciHMDB
beta-Resorcinolic acidHMDB
FEMA 3798HMDB
P-Hydroxysalicylic acidHMDB
Resorcinol-4-carboxylic acidHMDB
Resorcylic acid, betaHMDB
beta-Resorcylic acid, monosodium saltMeSH, HMDB
beta-Resorcylic acid, sodium saltMeSH, HMDB
beta-Resorcylic acid, lead saltMeSH, HMDB
β-Resorcinolic acidbiospider
β-Resorcylic acidbiospider
4-Dihydroxy-benzoateGenerator
4-DihydroxybenzoateGenerator
b-Resorcylic acid, 8CIdb_source
Benzoic acid, 2,4-dihydroxy-biospider
beta-Resorcylic acidbiospider
p-Hydroxysalicylic acidbiospider
Resorcylic acid, βbiospider
Predicted Properties
PropertyValueSource
Water Solubility12.4 g/LALOGPS
logP1.23ALOGPS
logP1.67ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.1ChemAxon
pKa (Strongest Basic)-5.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.28 m³·mol⁻¹ChemAxon
Polarizability13.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H6O4
IUPAC name2,4-dihydroxybenzoic acid
InChI IdentifierInChI=1S/C7H6O4/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,8-9H,(H,10,11)
InChI KeyUIAFKZKHHVMJGS-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1=C(O)C=C(O)C=C1
Average Molecular Weight154.121
Monoisotopic Molecular Weight154.026608673
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
  • Dihydroxybenzoic acid
  • Hydroxybenzoic acid
  • Salicylic acid
  • Salicylic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
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 54.55%; H 3.92%; O 41.52%DFC
    Melting PointMp 218-219° (213° rapid heat)DFC
    Boiling PointNot Available
    Experimental Water Solubility5.78 mg/mL at 25 oCBEILSTEIN
    Experimental logP1.63HANSCH,C ET AL. (1995)
    Experimental pKapKa3 14 (25°)DFC
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    GC-MS2,4-Dihydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0f79-5900000000-f66892920391d049309dSpectrum
    GC-MS2,4-Dihydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0f79-5900000000-f66892920391d049309dSpectrum
    Predicted GC-MS2,4-Dihydroxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udr-3900000000-e7332e7b36c8ef98cd3bSpectrum
    Predicted GC-MS2,4-Dihydroxybenzoic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05aj-4092000000-f022e8259d96401d388dSpectrum
    Predicted GC-MS2,4-Dihydroxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS2,4-Dihydroxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-5b06664c672085589e5d2017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0900000000-7defdd92875e0d2612f92017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-9400000000-34c2db0ddecca15891832017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-f371cbc9bab4c3b088632017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-86c98437f3097536f3ad2017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9700000000-d4cab43a400a6d1df5662017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-d8f66ec3df99ab1fe93a2021-09-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-2900000000-7d643edc32e6284ba4ca2021-09-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-47ed693761124857e43b2021-09-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0900000000-6cf094f769038fae172a2021-09-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-62579f22f3af1e4286f72021-09-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lu-9000000000-c2aabbc089de9d666fb42021-09-22View Spectrum
    NMRNot Available
    ChemSpider ID1446
    ChEMBL IDCHEMBL328910
    KEGG Compound IDNot Available
    Pubchem Compound ID1491
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID431
    DrugBank IDDB02839
    HMDB IDHMDB29666
    CRC / DFC (Dictionary of Food Compounds) IDBJR86-E:BJR86-E
    EAFUS ID931
    Dr. Duke ID2,4-DIHYDROXYBENZOIC-ACID
    BIGG IDNot Available
    KNApSAcK IDC00033542
    HET IDDOB
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDrw1097221
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite ID431
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    Flavours
    FlavorCitations
    mild
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    phenolic
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    Files
    MSDSNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
    — 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.