Pyridoxal (CED0001993)

Record Information
Version1.0
Creation Date2016-05-22 05:27:49 UTC
Update Date2026-08-25 06:10:42 UTC
Accession NumberCHEM018699
Identification
Common NamePyridoxal
ClassSmall Molecule
Description
Pyridoxal is an organic compound with the formula C8H9NO3 and an average molecular weight of 167.16 g/mol. Pyridoxal belongs to the pyridine carboxaldehydes, a subclass of pyridines and derivatives within the organic compounds. This compound has been identified in or released from 30 recorded sources. Within the category of food, food processing, and cookware, it is associated with fermentation processes for beer, the preparation of malt, food preservation, molasses and treatment of molasses, and agglomerated sugar products, among six other sources. In household cleaning and consumer products, it is found in bleaching agents, ash trays, cigar cigarettes, other smoking requisites, non electric simulated smoking devices, and five additional sources. It is also present in building and construction materials, specifically tents or canopies. Furthermore, it is found in electrical and electronic equipment, including amplifiers, antennas, discharge lamps, electric hearing aids, and conductors or conductive bodies characterised by the conductive materials, along with three other sources. Regarding its biological activity, pyridoxal has one recorded protein target, which is pyridoxal kinase (PDXK).
Contaminant TypeNot Available
Chemical Structure
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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-00di-2690000000-5d018202be238b10582aNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0aou-3974000000-8c963fdc714896ad343aNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-001j-0590000000-ed8a55680a0c9fa9cbafNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a4i-5695000000-bd3bb22a5dd4a600cb6cNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0aor-5895000000-e55e01ca30d17d2a8a72Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a4i-5695000000-bd3bb22a5dd4a600cb6cNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0aor-5895000000-e55e01ca30d17d2a8a72Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000i-1900000000-56d1f96c5ac868ce42a6Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00fs-6190000000-78d7f54ce0c5338f815fNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0900000000-4ce3f52baa36006ef4b2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00kg-9500000000-658a96f6cda4a96de045Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0gbc-9000000000-233fc8ab067b0dcd1f14Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-c49b207cafcf1c21302dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-cad83f5f123a879fa0bbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-4f12feae0e11a6d9016bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-2900000000-56fcdbb9b4363c84d2d0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-056r-9400000000-9700c9585f6c540bf007Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0gb9-0900000000-e646a99b0c1521d1c8ddNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-8fce1a7d8ceb3fced3edNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udl-6900000000-e2fc0eaa17e57d0a2556Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00kf-9200000000-0bda29931f8b6f2fcc77Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014l-9000000000-469c127d1aef4f8a51d7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2900000000-63ebef5a0818d6a1ccb8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05n0-0900000000-f468a00d88bedc116485Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-c49b207cafcf1c21302dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-bf0686eb8e3c28c30e85Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-686848e0f222273e5089Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-2900000000-99577e7f4a39e47c5c42Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-056r-9400000000-9700c9585f6c540bf007Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05n0-0900000000-f468a00d88bedc116485Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0gb9-0900000000-e646a99b0c1521d1c8ddNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-efa3bb6939a773839fa4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udl-6900000000-706331d9857f352a1e31Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00kf-9200000000-1970844d04848cfd3635Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014l-9000000000-469c127d1aef4f8a51d7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2900000000-63ebef5a0818d6a1ccb8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-c7fa3fe6b301c5f074e1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00kf-9000000000-9b3a140df63dbe8d0a7aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-6a0f52153163906fa3acNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014l-9000000000-9cad66caaa1e8fabf6c8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udl-5900000000-aac584f3a476bda1e0e7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-bd97f5bc4d391b181454Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4r-1900000000-f03c6e67ec131201e09eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05r0-9300000000-98ede09bbd6655752715Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-53345be81f950dd7a2e6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-685a964ebb07b4eb876fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-e65779203a7ec2b47cfaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-16eddf61d7042079638cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00ke-9800000000-68f7733397ebf500dc59Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-981ec5d66ec50d1d25e4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1900000000-c8378dddea1dccb09adaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-9000000000-3c8cb859d42266e19013Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uxr-0900000000-7f4ef736d1a810b2e8abNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-9c4ead9423b52a47b2feNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-9500000000-aa6a11948622748c8469Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0900000000-dd6386614990770eaae5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-e9de9bab2598f0316525Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0abc-9300000000-f4bc767c42577b6a1d5fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-cfda2ca4b4d82aaf521cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uk9-0900000000-54b410ff17d5d92faf9dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fl0-7900000000-6b0e05ef963346e09881Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4r-0900000000-761bebfcfb68ec2be973Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0900000000-cd98b24e8b66b398a756Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05mk-9500000000-da67e1a40519bc8f1b38Not AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2654.0Log mg/kg[1500:4700]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
541Agglomerated Sugar ProductsFood, food processing & cookwareNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
546Molasses And Treatment Of MolassesFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
554Ash TraysHousehold cleaning & consumer productsNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
599Harvesters For PeanutsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
36 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Pyridoxine-5'-phosphate oxidase structureClick to view 3D structurePyridoxine-5'-phosphate oxidaseQ9NVS9HumansPredicted (SEA)0.0778492
Click to view 3D structureP2X purinoceptor 1P47824Rattus norvegicusPredicted (SEA)3.89246
Click to view 3D structureP2X purinoceptor 3P49654Rattus norvegicusPredicted (SEA)2.10193
Click to view 3D structureL-lactate dehydrogenase B chainP16125Mus musculusPredicted (SEA)1.01204
Click to view 3D structureAromatic-L-amino-acid decarboxylaseO88533Mus musculusPredicted (SEA)3.58106
Click to view 3D structureThioredoxin reductase 2, mitochondrialQ9Z0J5Rattus norvegicusPredicted (SEA)0.622794
Click to view 3D structureP2X purinoceptor 1P51576Mus musculusPredicted (SEA)0.467095
Dihydrofolate reductase structureClick to view 3D structureDihydrofolate reductaseP0ABQ4Escherichia coli (strain K12)Predicted (SEA)91.4728
Click to view 3D structureDihydrofolate reductaseQ920D2Rattus norvegicusPredicted (SEA)107.354
Click to view 3D structureMannose-6-phosphate isomeraseP34949HumansPredicted (SEA)32.9302
Click to view 3D structureDihydrofolate reductaseQ59487Lactococcus lactis subsp. lactis (strain IL1403) (Streptococcuslactis)Predicted (SEA)13.0787
Click to view 3D structureThiamine transporter ThiTA2RI47Lactococcus lactis subsp. cremoris (strain MG1363)Predicted (SEA)4.12601
Click to view 3D structureLarge T antigenP03070Simian virus 40Predicted (SEA)152.04
Click to view 3D structureDihydrofolate reductaseP04174Neisseria gonorrhoeaePredicted (SEA)18.4503
Click to view 3D structureP2X purinoceptor 2P49653Rattus norvegicusPredicted (SEA)81.1189
Click to view 3D structureBifunctional dihydrofolate reductase-thymidylate synthaseQ27713Plasmodium berghei str. ANKAPredicted (SEA)24.6004
P2Y purinoceptor 1 structureClick to view 3D structureP2Y purinoceptor 1P47900HumansPredicted (SEA)242.345
Dihydrofolate reductase structureClick to view 3D structureDihydrofolate reductaseP00374HumansPredicted (SEA)454.25
Induced myeloid leukemia cell differentiation protein Mcl-1 structureClick to view 3D structureInduced myeloid leukemia cell differentiation protein Mcl-1Q07820HumansPredicted (SEA)1674.54
Click to view 3D structureSerine/threonine-protein kinase/endoribonuclease IRE1Q9EQY0Mus musculusPredicted (SEA)27.9479
Click to view 3D structureP2X purinoceptor 7Q99572HumansPredicted (SEA)384.419
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)5671.63
Dihydrofolate reductase structureClick to view 3D structureDihydrofolate reductaseP00381Lactobacillus caseiPredicted (SEA)312.798
P2X purinoceptor 1 structureClick to view 3D structureP2X purinoceptor 1P51575HumansPredicted (SEA)242.578
Click to view 3D structureDihydrofolate reductaseQ8Z9J9Salmonella enterica subsp. enterica serovar TyphiPredicted (SEA)98.09
Concentrations
Not Available
External Links
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.