Pyridoxal (CHEM018699)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:27:49 UTC
Update Date2016-11-09 01:15:51 UTC
Accession NumberCHEM018699
Identification
Common NamePyridoxal
ClassSmall Molecule
DescriptionA pyridinecarbaldehyde that is pyridine-4-carbaldehyde bearing methyl, hydroxy and hydroxymethyl substituents at positions 2, 3 and 5 respectively. The 4-carboxyaldehyde form of vitamin B6, it is converted into pyridoxal phosphate, a coenzyme for the synthesis of amino acids, neurotransmitters, sphingolipids and aminolevulinic acid.
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-HYDROXY-5-(hydroxymethyl)-2-methylisonicotinaldehydeChEBI
PyridoxaldehydeChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carboxaldehydeHMDB
Chemical FormulaC8H9NO3
Average Molecular Mass167.162 g/mol
Monoisotopic Mass167.058 g/mol
CAS Registry Number66-72-8
IUPAC Name3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde
Traditional Namepyridoxal
SMILESCC1=NC=C(CO)C(C=O)=C1O
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-2690000000-5d018202be238b10582aSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0aou-3974000000-8c963fdc714896ad343aSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001j-0590000000-ed8a55680a0c9fa9cbafSpectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0a4i-5695000000-bd3bb22a5dd4a600cb6cSpectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0aor-5895000000-e55e01ca30d17d2a8a72Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-5695000000-bd3bb22a5dd4a600cb6cSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0aor-5895000000-e55e01ca30d17d2a8a72Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1900000000-56d1f96c5ac868ce42a6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fs-6190000000-78d7f54ce0c5338f815fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-4ce3f52baa36006ef4b2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kg-9500000000-658a96f6cda4a96de045Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0gbc-9000000000-233fc8ab067b0dcd1f14Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-c49b207cafcf1c21302dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-0900000000-cad83f5f123a879fa0bbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-0900000000-4f12feae0e11a6d9016bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-2900000000-56fcdbb9b4363c84d2d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-056r-9400000000-9700c9585f6c540bf007Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0gb9-0900000000-e646a99b0c1521d1c8ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-0900000000-8fce1a7d8ceb3fced3edSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0udl-6900000000-e2fc0eaa17e57d0a2556Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00kf-9200000000-0bda29931f8b6f2fcc77Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014l-9000000000-469c127d1aef4f8a51d7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-2900000000-63ebef5a0818d6a1ccb8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-05n0-0900000000-f468a00d88bedc116485Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-c49b207cafcf1c21302dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-bf0686eb8e3c28c30e85Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0900000000-686848e0f222273e5089Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-2900000000-99577e7f4a39e47c5c42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0900000000-7f4ef736d1a810b2e8abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-9c4ead9423b52a47b2feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9500000000-aa6a11948622748c8469Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-dd6386614990770eaae5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-e9de9bab2598f0316525Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9300000000-f4bc767c42577b6a1d5fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00147
HMDB IDHMDB0001545
FooDB IDFDB011169
Phenol Explorer IDNot Available
KNApSAcK IDC00007509
BiGG ID34393
BioCyc IDPYRIDOXAL
METLIN ID6312
PDB IDNot Available
Wikipedia LinkPyridoxal
Chemspider ID1021
ChEBI ID17310
PubChem Compound ID1050
Kegg Compound IDC00250
YMDB IDYMDB00392
ECMDB IDECMDB01545
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17765195
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20381632
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23801094
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24365359
6. Fujimoto, Yasuo. Pyridoxal. Jpn. Tokkyo Koho (1971), 2 pp.
7. Coburn SP, Mahuren JD, Pauly TA, Ericson KL, Townsend DW: Alkaline phosphatase activity and pyridoxal phosphate concentrations in the milk of various species. J Nutr. 1992 Dec;122(12):2348-53. doi: 10.1093/jn/122.12.2348.
8. Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309.
9. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.
10. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.
11. Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.
12. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.
13. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386
14. Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013
15. Fujimoto, Yasuo. Pyridoxal. Jpn. Tokkyo Koho (1971), 2 pp.
16. Rajamohan F, Nelms L, Joslin DL, Lu B, Reagan WJ, Lawton M: cDNA cloning, expression, purification, distribution, and characterization of biologically active canine alanine aminotransferase-1. Protein Expr Purif. 2006 Jul;48(1):81-9. Epub 2006 Jan 30.
17. Huang YC, Lan PH, Cheng CH, Lee BJ, Kan MN: Vitamin B6 intakes and status of mechanically ventilated critically ill patients in Taiwan. Eur J Clin Nutr. 2002 May;56(5):387-92.
18. Fonda ML: Vitamin B6 metabolism and binding to proteins in the blood of alcoholic and nonalcoholic men. Alcohol Clin Exp Res. 1993 Dec;17(6):1171-8.
19. el-Habet AE, el-Sewedy SM, el-Sharaky A, Gaafar NK, Abdel-Rafee A, Hamoud F: Biochemical studies on bilharzial and nonbilharzial hyperoxaluria: effect of pyridoxine and allopurinol treatment. Biochem Med Metab Biol. 1987 Aug;38(1):1-8.
20. Mehansho H, Henderson LM: Transport and accumulation of pyridoxine and pyridoxal by erythrocytes. J Biol Chem. 1980 Dec 25;255(24):11901-7.
21. Kark JA, Bongiovanni R, Hicks CU, Tarassoff PG, Hannah JS, Yoshida GY: Modification of intracellular hemoglobin with pyridoxal and pyridoxal 5'-phosphate. Blood Cells. 1982;8(2):299-314.
22. Bosse TR, Donald EA: The vitamin B6 requirement in oral contraceptive users. I. Assessment by pyridoxal level and transferase activity in erythrocytes. Am J Clin Nutr. 1979 May;32(5):1015-23.
23. Linares P, Luque de Castro MD, Valcarcel M: Simultaneous determination of pyridoxal and pyridoxal 5-phosphate in human serum by flow injection analysis. Anal Chem. 1985 Sep;57(11):2101-6.
24. Schenker S, Johnson RF, Mahuren JD, Henderson GI, Coburn SP: Human placental vitamin B6 (pyridoxal) transport: normal characteristics and effects of ethanol. Am J Physiol. 1992 Jun;262(6 Pt 2):R966-74.
25. Brenner A, Wapnir RA: A pyridoxine-dependent behavioral disorder unmasked by isoniazid. Am J Dis Child. 1978 Aug;132(8):773-6.
26. Kark JA, Tarassoff PG, Bongiovanni R: Pyridoxal phosphate as an antisickling agent in vitro. J Clin Invest. 1983 May;71(5):1224-9.
27. Yiakouvaki A, Savovic J, Al-Qenaei A, Dowden J, Pourzand C: Caged-iron chelators a novel approach towards protecting skin cells against UVA-induced necrotic cell death. J Invest Dermatol. 2006 Oct;126(10):2287-95. Epub 2006 May 18.