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Pyridoxal

From Wikipedia, the free encyclopedia
Not to be confused with pyridoxol, which ispyridoxine.
Pyridoxal
Skeletal formula of pyridoxal
Skeletal formula of pyridoxal
Ball-and-stick model of pyridoxal
Ball-and-stick model of pyridoxal
Ball-and-stick model based on thecrystal structure.[1][2] Note that the acidicphenol group has donated a proton to the basicpyridine group to form azwitterion, and thehydroxymethyl group has reacted with thealdehyde group to form ahemiacetal.
Names
Preferred IUPAC name
3-Hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.000.573Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,4,10,12H,3H2,1H3 checkY
    Key: RADKZDMFGJYCBB-UHFFFAOYSA-N checkY
  • InChI=1/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,4,10,12H,3H2,1H3
    Key: RADKZDMFGJYCBB-UHFFFAOYAP
  • O=Cc1c(O)c(C)ncc1CO
Properties
C8H9NO3
Molar mass167.16 g/mol
Melting point165 °C (329 °F; 438 K) (decomposes)
Related compounds
Related arylformaldehydes
Damnacanthal

Gossypol

Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Pyridoxal (PL)[3] is one form ofvitamin B6.

Some medically relevant bacteria, such as those in the generaGranulicatella andAbiotrophia, require pyridoxal for growth. This nutritional requirement can lead to the culture phenomenon of satellite growth. Inin vitro culture, these pyridoxal-dependent bacteria may only grow in areas surrounding colonies of bacteria from other genera ("satellitism") that are capable of producing pyridoxal.

Pyridoxal is involved in what is believed to be the most ancient reaction of aerobic metabolism on Earth, about 2.9 billion years ago, a forerunner of theGreat Oxidation Event.[4]

See also

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References

[edit]
  1. ^"CSD Entry: BIHKEI01".Cambridge Structural Database: Access Structures.Cambridge Crystallographic Data Centre. 1985.Archived from the original on 2023-11-04. Retrieved2023-11-04.
  2. ^MacLaurin, C. L.; Richardson, M. F. (1985). "Pyridoxal, C8H9NO3, and pyridoxamine dihydrate, C8H12N2O2.2H2O".Acta Crystallogr. C.41 (2):261–263.Bibcode:1985AcCrC..41..261M.doi:10.1107/S0108270185003547.
  3. ^"Vitamin B-6".iupac.qmul.ac.uk. Retrieved2024-09-26.
  4. ^"Protein Domain Structure Uncovers the Origin of Aerobic Metabolism and the Rise of Planetary Oxygen", Gustavo Caetano-Anolles et al., published inStructure; paper available from University of Illinois News Bureau, 2012.
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