Record Information
Version1.0
Creation date2010-04-08 22:09:30 UTC
Update date2020-09-17 15:38:58 UTC
Primary IDFDB011169
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePyridoxal
DescriptionPyridoxal, also known as pyridoxaldehyde, belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives are compounds containing a pyridoxal moiety, which consists of a pyridine ring substituted at positions 2,3,4, and 5 by a methyl group, a hydroxyl group, a carbaldehyde group, and a hydroxymethyl group, respectively. The 4-carboxyaldehyde form of vitamin B 6 which is converted to pyridoxal phosphate which is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. Pyridoxal is a strong basic compound (based on its pKa). Pyridoxal exists in all living species, ranging from bacteria to humans. In humans, pyridoxal is involved in glycine and serine metabolism. Outside of the human body, Pyridoxal is found, on average, in the highest concentration within milk (cow). Pyridoxal has also been detected, but not quantified in, several different foods, such as tarragons, peppermints, jicama, shallots, and dandelions. This could make pyridoxal a potential biomarker for the consumption of these foods. Pyridoxal is a potentially toxic compound. Pyridoxal is the precursor to pyridoxal phosphate.
CAS Number66-72-8
Structure
Thumb
Synonyms
SynonymSource
3-HYDROXY-5-(hydroxymethyl)-2-methylisonicotinaldehydeChEBI
PyridoxaldehydeChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carboxaldehydeHMDB
3-HYDROXY-5-(HYDROXYMETHYL)-2-METHYLISONICOTINALDEHYDEbiospider
3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehydebiospider
3-Hydroxy-5-hydroxymethyl-2-methyl-4-pyridincarbaldehydbiospider
3-Hydroxy-5-hydroxymethyl-2-methyl-4-pyridinecarboxaldehyde, 9CIdb_source
3-Hydroxy-5-hydroxymethyl-2-methylisonicotinic aldehydedb_source
PLbiospider
PXLbiospider
Vitamin B6 hydrochloridebiospider
Predicted Properties
PropertyValueSource
Water Solubility11.7 g/LALOGPS
logP0.02ALOGPS
logP0.18ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)7.97ChemAxon
pKa (Strongest Basic)4.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.42 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.87 m³·mol⁻¹ChemAxon
Polarizability16.28 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H9NO3
IUPAC name3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde
InChI IdentifierInChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,4,10,12H,3H2,1H3
InChI KeyRADKZDMFGJYCBB-UHFFFAOYSA-N
Isomeric SMILESCC1=NC=C(CO)C(C=O)=C1O
Average Molecular Weight167.162
Monoisotopic Molecular Weight167.058243159
Classification
Description Belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives are compounds containing a pyridoxal moiety, which consists of a pyridine ring substituted at positions 2,3,4, and 5 by a methyl group, a hydroxyl group, a carbaldehyde group, and a hydroxymethyl group, respectively.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridine carboxaldehydes
Direct ParentPyridoxals and derivatives
Alternative Parents
Substituents
  • Pyridoxal
  • Aryl-aldehyde
  • Hydroxypyridine
  • Methylpyridine
  • Vinylogous acid
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Aldehyde
  • Alcohol
  • Organic oxygen compound
  • Aromatic alcohol
  • Organic nitrogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 57.48%; H 5.43%; N 8.38%; O 28.71%DFC
Melting Point165 oC
Boiling PointNot Available
Experimental Water Solubility500 mg/mLCOFFEN,DL (1978)
Experimental logPNot Available
Experimental pKapKa3 13 (25°)DFC
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPyridoxal, non-derivatized, GC-MS Spectrumsplash10-00di-2690000000-5d018202be238b10582aSpectrum
GC-MSPyridoxal, non-derivatized, GC-MS Spectrumsplash10-0aou-3974000000-8c963fdc714896ad343aSpectrum
GC-MSPyridoxal, non-derivatized, GC-MS Spectrumsplash10-001j-0590000000-ed8a55680a0c9fa9cbafSpectrum
GC-MSPyridoxal, 1 MEOX; 2 TMS, GC-MS Spectrumsplash10-0a4i-5695000000-bd3bb22a5dd4a600cb6cSpectrum
GC-MSPyridoxal, 1 MEOX; 2 TMS, GC-MS Spectrumsplash10-0aor-5895000000-e55e01ca30d17d2a8a72Spectrum
GC-MSPyridoxal, non-derivatized, GC-MS Spectrumsplash10-0a4i-5695000000-bd3bb22a5dd4a600cb6cSpectrum
GC-MSPyridoxal, non-derivatized, GC-MS Spectrumsplash10-0aor-5895000000-e55e01ca30d17d2a8a72Spectrum
Predicted GC-MSPyridoxal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-1900000000-56d1f96c5ac868ce42a6Spectrum
Predicted GC-MSPyridoxal, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fs-6190000000-78d7f54ce0c5338f815fSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-c49b207cafcf1c21302dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-0900000000-cad83f5f123a879fa0bbSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-0900000000-4f12feae0e11a6d9016bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-2900000000-56fcdbb9b4363c84d2d0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-056r-9400000000-9700c9585f6c540bf007Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-05n0-0900000000-f468a00d88bedc116485Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-c49b207cafcf1c21302dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-bf0686eb8e3c28c30e85Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0900000000-686848e0f222273e5089Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-2900000000-99577e7f4a39e47c5c42Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-056r-9400000000-9700c9585f6c540bf007Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-05n0-0900000000-f468a00d88bedc116485Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-bd97f5bc4d391b181454Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-1900000000-f03c6e67ec131201e09eSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-05r0-9300000000-98ede09bbd6655752715Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-4ce3f52baa36006ef4b2Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kg-9500000000-658a96f6cda4a96de045Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0gbc-9000000000-233fc8ab067b0dcd1f14Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0gb9-0900000000-e646a99b0c1521d1c8ddSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-0900000000-8fce1a7d8ceb3fced3edSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0udl-6900000000-e2fc0eaa17e57d0a2556Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00kf-9200000000-0bda29931f8b6f2fcc77Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014l-9000000000-469c127d1aef4f8a51d7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-2900000000-63ebef5a0818d6a1ccb8Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0gb9-0900000000-e646a99b0c1521d1c8ddSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID1021
ChEMBL IDCHEMBL102970
KEGG Compound IDC00250
Pubchem Compound ID1050
Pubchem Substance IDNot Available
ChEBI ID17310
Phenol-Explorer IDNot Available
DrugBank IDDB00147
HMDB IDHMDB01545
CRC / DFC (Dictionary of Food Compounds) IDGCG08-L:GCG08-L
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34393
KNApSAcK IDC00007509
HET IDPXL
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPyridoxal
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glycine dehydrogenase [decarboxylating], mitochondrialGLDCP23378
Pathways
NameSMPDB LinkKEGG Link
Vitamin B6 MetabolismSMP00017 map00750
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference