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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:31:55 UTC
Update Date2022-03-07 02:52:14 UTC
HMDB IDHMDB0029666
Secondary Accession Numbers
  • HMDB29666
Metabolite Identification
Common 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 coffee and coffee products, alcoholic beverages, robusta coffees (Coffea canephora), arabica coffees (Coffea arabica), and fruits. 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.
Structure
Data?1582753448
Synonyms
ValueSource
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
Chemical FormulaC7H6O4
Average Molecular Weight154.121
Monoisotopic Molecular Weight154.026608673
IUPAC Name2,4-dihydroxybenzoic acid
Traditional Name2,4-dihydroxybenzoic acid
CAS Registry Number89-86-1
SMILES
OC(=O)C1=C(O)C=C(O)C=C1
InChI Identifier
InChI=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
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
  • 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

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point218 - 219 °CNot Available
Boiling Point309.00 to 310.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility5.78 mg/mL at 25 °CNot Available
LogP1.63Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.40331661259
DarkChem[M-H]-129.25431661259
DeepCCS[M+H]+133.07730932474
DeepCCS[M-H]-130.03130932474
DeepCCS[M-2H]-166.96930932474
DeepCCS[M+Na]+142.47130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,4-Dihydroxybenzoic acidOC(=O)C1=C(O)C=C(O)C=C12952.6Standard polar33892256
2,4-Dihydroxybenzoic acidOC(=O)C1=C(O)C=C(O)C=C11606.9Standard non polar33892256
2,4-Dihydroxybenzoic acidOC(=O)C1=C(O)C=C(O)C=C11521.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,4-Dihydroxybenzoic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(O)C=C1O1781.4Semi standard non polar33892256
2,4-Dihydroxybenzoic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC=C1C(=O)O1744.8Semi standard non polar33892256
2,4-Dihydroxybenzoic acid,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(C(=O)O)C(O)=C11781.5Semi standard non polar33892256
2,4-Dihydroxybenzoic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C)C=C1O1728.6Semi standard non polar33892256
2,4-Dihydroxybenzoic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC=C(O)C=C1O[Si](C)(C)C1772.3Semi standard non polar33892256
2,4-Dihydroxybenzoic acid,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(C(=O)O)C(O[Si](C)(C)C)=C11798.7Semi standard non polar33892256
2,4-Dihydroxybenzoic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C1822.4Semi standard non polar33892256
2,4-Dihydroxybenzoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O)C=C1O2029.3Semi standard non polar33892256
2,4-Dihydroxybenzoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC=C1C(=O)O2002.0Semi standard non polar33892256
2,4-Dihydroxybenzoic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)O)C(O)=C12032.3Semi standard non polar33892256
2,4-Dihydroxybenzoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O2211.8Semi standard non polar33892256
2,4-Dihydroxybenzoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C2236.1Semi standard non polar33892256
2,4-Dihydroxybenzoic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)O)C(O[Si](C)(C)C(C)(C)C)=C12301.2Semi standard non polar33892256
2,4-Dihydroxybenzoic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2461.3Semi standard non polar33892256
Spectra

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.102 +/- 0.022 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.099 +/- 0.027 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.096 +/- 0.025 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.142 +/- 0.03 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.113 +/- 0.024 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.116 +/- 0.022 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.104 +/- 0.017 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.632 +/- 0.539 uMAdult (>18 years old)Male
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 431 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 431 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.084 +/- 0.019 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02839
Phenol Explorer Compound ID431
FooDB IDFDB000842
KNApSAcK IDC00033542
Chemspider ID1446
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2,4-Dihydroxybenzoic acid
METLIN IDNot Available
PubChem Compound1491
PDB IDDOB
ChEBI ID248101
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1015101
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

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
2,4-Dihydroxybenzoic acid → 6-(4-carboxy-3-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2,4-Dihydroxybenzoic acid → 6-(2-carboxy-5-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2,4-Dihydroxybenzoic acid → 6-(2,4-dihydroxybenzoyloxy)-3,4,5-trihydroxyoxane-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
2,4-Dihydroxybenzoic acid → 2-{[(2,4-dihydroxyphenyl)(hydroxy)methylidene]amino}acetic aciddetails