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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2013-04-09 21:16:38 UTC
Update Date2019-07-23 07:13:18 UTC
HMDB IDHMDB0059965
Secondary Accession Numbers
  • HMDB59965
Metabolite Identification
Common Name3,4-Dihydroxybenzaldehyde
Description3,4-Dihydroxybenzaldehyde, also known as protocatechuic aldehyde, is a phenolic aldehyde, a compound released from cork stoppers into wine. This molecule can be used as a precursor in vanillin synthesis via biotransformation by cell cultures of Capsicum frutescens, a type of chili pepper. It is also found in the mushroom Phellinus linteus (Wikipedia).
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
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
DescriptionThis compound 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 ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzaldehydes
Direct ParentHydroxybenzaldehydes
Alternative Parents
Substituents
  • Hydroxybenzaldehyde
  • 1,2-diphenol
  • Benzoyl
  • Aryl-aldehyde
  • Phenol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-2900000000-fd0d28650a72226166e6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00yi-8690000000-16ccc54dcf22361cffb1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0040900010-522c055741661bbc5ba8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0002-0040900010-522c055741661bbc5ba8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0002-0040900010-522c055741661bbc5ba8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-002r-0905000000-7987816fb8648b0eea18JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0900000000-aa91c9c469ec39450435JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-000i-0900000000-25b5b2bc87af9df04e91JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0900000000-03d9e2dbe57c9bcfb9abJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-002r-0905000000-7987816fb8648b0eea18JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-0900000000-aa91c9c469ec39450435JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-0900000000-25b5b2bc87af9df04e91JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-db13978cfcbc33c6da32JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-ed3a0258f14e4361b25cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9200000000-cdb54c91531419396213JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-db13978cfcbc33c6da32JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-ed3a0258f14e4361b25cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9200000000-cdb54c91531419396213JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-882b8375384be94a3491JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-25b2a170eaf9dd74c4a0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kw4-9300000000-e349b638bc98dcdf0adeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-882b8375384be94a3491JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-25b2a170eaf9dd74c4a0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kw4-9300000000-e349b638bc98dcdf0adeJSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified3.577 +/- 0.566 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID723
FoodDB IDFDB012060
KNApSAcK IDNot Available
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
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 ]