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Record Information
Version4.0
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
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:

Role

Industrial application:

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
Water Solubility14.3 g/LALOGPS
logP0.89ALOGPS
logP1.08ChemAxon
logS-0.99ALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-2900000000-fd0d28650a72226166e6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00yi-8690000000-16ccc54dcf22361cffb1Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0040900010-522c055741661bbc5ba8Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0002-0040900010-522c055741661bbc5ba8Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0002-0040900010-522c055741661bbc5ba8Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-002r-0905000000-7987816fb8648b0eea18Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0900000000-aa91c9c469ec39450435Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-000i-0900000000-25b5b2bc87af9df04e91Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0900000000-03d9e2dbe57c9bcfb9abSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-002r-0905000000-7987816fb8648b0eea18Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-0900000000-aa91c9c469ec39450435Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-0900000000-25b5b2bc87af9df04e91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-db13978cfcbc33c6da32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-ed3a0258f14e4361b25cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9200000000-cdb54c91531419396213Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-db13978cfcbc33c6da32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-ed3a0258f14e4361b25cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9200000000-cdb54c91531419396213Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-882b8375384be94a3491Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-25b2a170eaf9dd74c4a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kw4-9300000000-e349b638bc98dcdf0adeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-882b8375384be94a3491Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-25b2a170eaf9dd74c4a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kw4-9300000000-e349b638bc98dcdf0adeSpectrum
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 ID
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 ]