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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2013-04-09 21:16:38 UTC
Update Date2020-11-09 23:21:30 UTC
HMDB IDHMDB0059965
Secondary Accession Numbers
  • HMDB59965
Metabolite Identification
Common Name3,4-Dihydroxybenzaldehyde
Description3,4-Dihydroxybenzaldehyde, also known as protocatechualdehyde or 1,2-dihydroxy-4-formylbenzene, belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. 3,4-Dihydroxybenzaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,4-Dihydroxybenzaldehyde is an almond, bitter, and dry tasting compound. Outside of the human body, 3,4-Dihydroxybenzaldehyde is found, on average, in the highest concentration within vinegars and grape wines. 3,4-Dihydroxybenzaldehyde has also been detected, but not quantified in, several different foods, such as orange bell peppers, common wheats, spelts, horseradish tree, and muskmelons. This could make 3,4-dihydroxybenzaldehyde a potential biomarker for the consumption of these foods.
Structure
Data?1563865998
Synonyms
ValueSource
1,2-Dihydroxy-4-formylbenzeneChEBI
3,4-DihydroxybenzenecarbonalChEBI
4-Formyl-1,2-benzenediolChEBI
4-Formyl-1,2-dihydroxybenzeneChEBI
ProtocatechualdehydeChEBI
Protocatechuic aldehydeChEBI
Protocatechualdehyde, 3H-labeledMeSH
Rancinamycin IVMeSH
Protocatechualdehyde, formyl-14C-labeledMeSH
3,4-DihydroxybenzaldehydeHMDB
Chemical FormulaC7H6O3
Average Molecular Weight138.1207
Monoisotopic Molecular Weight138.031694058
IUPAC Name3,4-dihydroxybenzaldehyde
Traditional Name3,4-dihydroxybenzaldehyde
CAS Registry Number139-85-5
SMILES
OC1=CC=C(C=O)C=C1O
InChI Identifier
InChI=1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H
InChI KeyIBGBGRVKPALMCQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentHydroxybenzaldehydes
Alternative Parents
Substituents
  • Hydroxybenzaldehyde
  • Catechol
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility14.3 g/LALOGPS
logP10(0.89) g/LALOGPS
logP10(1.08) g/LChemAxon
logS10(-0.99) g/LALOGPS
pKa (Strongest Acidic)7.46ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.6 m³·mol⁻¹ChemAxon
Polarizability12.87 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+127.5931661259
DarkChem[M-H]-124.83731661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-Dihydroxybenzaldehyde,1TMS,#1C[Si](C)(C)OC1=CC=C(C=O)C=C1O1535.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
3,4-Dihydroxybenzaldehyde,1TMS,#2C[Si](C)(C)OC1=CC(C=O)=CC=C1O1512.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
3,4-Dihydroxybenzaldehyde,2TMS,#1C[Si](C)(C)OC1=CC=C(C=O)C=C1O[Si](C)(C)C1619.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
3,4-Dihydroxybenzaldehyde,1TBDMS,#1CC(C)(C)[Si](C)(C)OC1=CC=C(C=O)C=C1O1804.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
3,4-Dihydroxybenzaldehyde,1TBDMS,#2CC(C)(C)[Si](C)(C)OC1=CC(C=O)=CC=C1O1772.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
3,4-Dihydroxybenzaldehyde,2TBDMS,#1CC(C)(C)[Si](C)(C)OC1=CC=C(C=O)C=C1O[Si](C)(C)C(C)(C)C2070.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxybenzaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-2900000000-fd0d28650a72226166e62017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxybenzaldehyde GC-MS (2 TMS) - 70eV, Positivesplash10-00yi-8690000000-16ccc54dcf22361cffb12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxybenzaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde ESI-TOF 10V, Negative-QTOFsplash10-0002-0040900010-522c055741661bbc5ba82017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde ESI-TOF 20V, Negative-QTOFsplash10-0002-0040900010-522c055741661bbc5ba82017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde ESI-TOF , Negative-QTOFsplash10-0002-0040900010-522c055741661bbc5ba82017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde ESI-TOF 10V, Negative-QTOFsplash10-002r-0905000000-7987816fb8648b0eea182017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde ESI-TOF 10V, Negative-QTOFsplash10-000i-0900000000-aa91c9c469ec394504352017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde ESI-TOF 20V, Negative-QTOFsplash10-000i-0900000000-25b5b2bc87af9df04e912017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde ESI-TOF , Negative-QTOFsplash10-000i-0900000000-03d9e2dbe57c9bcfb9ab2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde ESI-TOF 10V, Negative-QTOFsplash10-002r-0905000000-7987816fb8648b0eea182017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde LC-ESI-TOF , negative-QTOFsplash10-000i-0900000000-aa91c9c469ec394504352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde LC-ESI-TOF , negative-QTOFsplash10-000i-0900000000-25b5b2bc87af9df04e912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde 10V, Positive-QTOFsplash10-000i-0900000000-aa91c9c469ec394504352021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde 20V, Positive-QTOFsplash10-000i-0900000000-25b5b2bc87af9df04e912021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde 10V, Positive-QTOFsplash10-000i-0900000000-db13978cfcbc33c6da322015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde 20V, Positive-QTOFsplash10-000i-1900000000-ed3a0258f14e4361b25c2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde 40V, Positive-QTOFsplash10-0pb9-9200000000-cdb54c915314193962132015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde 10V, Positive-QTOFsplash10-000i-0900000000-db13978cfcbc33c6da322015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde 20V, Positive-QTOFsplash10-000i-1900000000-ed3a0258f14e4361b25c2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde 40V, Positive-QTOFsplash10-0pb9-9200000000-cdb54c915314193962132015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde 10V, Negative-QTOFsplash10-000i-0900000000-882b8375384be94a34912015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde 20V, Negative-QTOFsplash10-000i-1900000000-25b2a170eaf9dd74c4a02015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde 40V, Negative-QTOFsplash10-0kw4-9300000000-e349b638bc98dcdf0ade2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde 10V, Negative-QTOFsplash10-000i-0900000000-882b8375384be94a34912015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde 20V, Negative-QTOFsplash10-000i-1900000000-25b2a170eaf9dd74c4a02015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzaldehyde 40V, Negative-QTOFsplash10-0kw4-9300000000-e349b638bc98dcdf0ade2015-05-27Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.577 +/- 0.566 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11268
Phenol Explorer Compound ID723
FooDB IDFDB012060
KNApSAcK IDC00018099
Chemspider ID8438
KEGG Compound IDC16700
BioCyc IDCPD-7616
BiGG IDNot Available
Wikipedia LinkProtocatechuic aldehyde
METLIN IDNot Available
PubChem Compound8768
PDB IDNot Available
ChEBI ID50205
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Loke WM, Jenner AM, Proudfoot JM, McKinley AJ, Hodgson JM, Halliwell B, Croft KD: A metabolite profiling approach to identify biomarkers of flavonoid intake in humans. J Nutr. 2009 Dec;139(12):2309-14. doi: 10.3945/jn.109.113613. Epub 2009 Oct 7. [PubMed:19812218 ]