Showing Compound Card for 3,4-dihydroxybenzoic acid (CDB006364)

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Record Information
Version1.0
Created at2020-11-02 22:39:04 UTC
Updated at2022-12-13 19:31:27 UTC
CannabisDB IDCDB006364
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name3,4-dihydroxybenzoic acid
DescriptionProtocatechuic acid, also known as protocatechuate or 3,4-dihydroxybenzoate, 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. A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. Protocatechuic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Protocatechuic acid has been detected, but not quantified in, several different foods, such as dills, nuts, fireweeds, almonds, and muscadine grapes. This could make protocatechuic acid a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4,5-Dihydroxybenzoic acidChEBI
4-Carboxy-1,2-dihydroxybenzeneChEBI
Protocatehuic acidChEBI
3,4-Dihydroxybenzoic acidKegg
ProtocatechuateKegg
4,5-DihydroxybenzoateGenerator
ProtocatehuateGenerator
3,4-DihydroxybenzoateGenerator
Protocatechuic acid, monosodium saltHMDB
Protocatechuic acid, carboxy-14C-labeledHMDB
2,4-DihydroxybenzoateHMDB
2,4-Dihydroxybenzoic acidHMDB
b-ResorcylateHMDB
b-Resorcylic acidHMDB
beta-ResorcylateHMDB
beta-Resorcylic acidHMDB
3,4-DHBAHMDB
1,2-Dihydroxybenzene-4-carboxylic acidPhytoBank
Protocatechoic acidPhytoBank
Proto-catechuic acidPhytoBank
Protocatechuic acidHMDB
Chemical FormulaC7H6O4
Average Molecular Weight154.121
Monoisotopic Molecular Weight154.026608673
IUPAC Name3,4-dihydroxybenzoic acid
Traditional Name3,4-dihydroxybenzoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)
InChI KeyYQUVCSBJEUQKSH-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
  • Benzoic acid
  • Benzoyl
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.32ALOGPS
logP1.02ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.28 m³·mol⁻¹ChemAxon
Polarizability13.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS3,4-dihydroxybenzoic acid, 3 TMS, GC-MS Spectrumsplash10-0006-0913000000-0933eeed3701393aa41fSpectrum
GC-MS3,4-dihydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0006-0911000000-ca1452bfe34749c0d8c1Spectrum
GC-MS3,4-dihydroxybenzoic acid, 3 TMS, GC-MS Spectrumsplash10-00dl-9711000000-595a58baf84bb73670aeSpectrum
GC-MS3,4-dihydroxybenzoic acid, 3 TMS, GC-MS Spectrumsplash10-0006-4912000000-a095cbdb4d3809a9b775Spectrum
GC-MS3,4-dihydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0gb9-9800000000-f08a8e55f19d388091c0Spectrum
GC-MS3,4-dihydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0006-0913000000-0933eeed3701393aa41fSpectrum
GC-MS3,4-dihydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0006-0911000000-ca1452bfe34749c0d8c1Spectrum
GC-MS3,4-dihydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00dl-9711000000-595a58baf84bb73670aeSpectrum
GC-MS3,4-dihydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0006-4912000000-a095cbdb4d3809a9b775Spectrum
GC-MS3,4-dihydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0006-0911000000-c141d09a094e57440cd4Spectrum
Predicted GC-MS3,4-dihydroxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-114r-2900000000-ad8c99ac8e347f2d0a02Spectrum
Predicted GC-MS3,4-dihydroxybenzoic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05aj-4092000000-dfefa4fd6fad51de9dbcSpectrum
Predicted GC-MS3,4-dihydroxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,4-dihydroxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-9e8a76eec66c42952ee92012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0296-9100000000-145f71b183841a31fdc82012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-9044e5839d8d0b8f8ee62012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0gb9-9800000000-f08a8e55f19d388091c02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-0900000000-58c9b8232fbc187217d42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0900000000-58c9b8232fbc187217d42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-0900000000-43a650326b83e2dfe5892017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-0900000000-61ebd9558aeeb60dda892017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6900000000-dbc2159e590d48566b2c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0900000000-e6774ca1e916f97ad70d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0900000000-0bc46bd9df728e43dc632021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-0d999db8c8012fe5222c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-7ecb0cf92a0c6bd881502021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0900000000-99ac3661fc7809f287962015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0900000000-df55ffdd340947acfac92015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc9-9500000000-201668ae66ab0379946f2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0900000000-99ac3661fc7809f287962015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0900000000-df55ffdd340947acfac92015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc9-9500000000-201668ae66ab0379946f2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-0595d63853a488b9c6cf2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0900000000-d794b62eb087aaa84f942015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9700000000-32a6fa42639cb300cdc92015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-0595d63853a488b9c6cf2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0900000000-d794b62eb087aaa84f942015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9700000000-32a6fa42639cb300cdc92015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, 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, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.0451 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.0253 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.0224 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.0426 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.0213 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.0336 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0001856
DrugBank IDDB03946
Phenol Explorer Compound ID412
FoodDB IDFDB031135
KNApSAcK IDC00002668
Chemspider ID71
KEGG Compound IDC00230
BioCyc ID3-4-DIHYDROXYBENZOATE
BiGG IDNot Available
Wikipedia LinkProtocatechuic_acid
METLIN ID6350
PubChem Compound72
PDB IDNot Available
ChEBI ID36062
References
General ReferencesNot Available