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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:31:55 UTC
Update Date2020-11-09 23:19:55 UTC
HMDB IDHMDB0029666
Secondary Accession Numbers
  • HMDB29666
Metabolite Identification
Common Name2,4-Dihydroxybenzoic acid
Description2,4-Dihydroxybenzoic acid, also known as b-resorcylic acid or 4-hydroxysalicylic 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 an extremely weak basic (essentially neutral) compound (based on its pKa). 2,4-Dihydroxybenzoic acid is a mild and phenolic tasting compound. Outside of the human body, 2,4-Dihydroxybenzoic acid is found, on average, in the highest concentration within american cranberries and olives. 2,4-Dihydroxybenzoic acid has also been detected, but not quantified in, several different foods, such as alcoholic beverages, coffee and coffee products, fruits, and german camomiles. This could make 2,4-dihydroxybenzoic acid a potential biomarker for the consumption of these foods. 2,4-Dihydroxybenzoic acid (β-resorcylic acid) is a dihydroxybenzoic acid. As a resorcylic acid, it is one of the three isomeric crystalline acids that are both carboxyl derivatives of resorcinol and dihydroxy derivatives of benzoic acid. It is a degradation product of cyanidin glycosides from tart cherries in cell cultures. It is also a metabolite found in human plasma after cranberry juice consumption.
Structure
Data?1582753448
Synonyms
ValueSource
2,4-DihydroxybenzoateGenerator
24-Dihydroxybenzoic acidHMDB
24-Dihydroxy-benzoic acidHMDB
Beta-Resorcylic acidHMDB
24-DihydroxybenzoateHMDB
24-Dihydroxy-benzoateHMDB
b-ResorcylateHMDB
b-Resorcylic acidHMDB
beta-ResorcylateHMDB
Β-resorcylateHMDB
Β-resorcylic acidHMDB
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 saltHMDB
beta-Resorcylic acid, sodium saltHMDB
beta-Resorcylic acid, lead saltHMDB
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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point218 - 219 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.78 mg/mL at 25 °CNot Available
LogP1.63Not Available
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
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f79-5900000000-f66892920391d049309d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f79-5900000000-f66892920391d049309d2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-3900000000-e7332e7b36c8ef98cd3b2017-07-27View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-05aj-4092000000-f022e8259d96401d388d2017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udr-3900000000-e1633778950d594347cb2021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-5b06664c672085589e5d2017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0900000000-7defdd92875e0d2612f92017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-9400000000-34c2db0ddecca15891832017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-f371cbc9bab4c3b088632017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-86c98437f3097536f3ad2017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9700000000-d4cab43a400a6d1df5662017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-d8f66ec3df99ab1fe93a2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-2900000000-7d643edc32e6284ba4ca2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-47ed693761124857e43b2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0900000000-6cf094f769038fae172a2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-62579f22f3af1e4286f72021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lu-9000000000-c2aabbc089de9d666fb42021-09-07View 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
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