Pyridoxal

Pyridoxal
	; Idealised skeletal formula
	; Ball-and-stick model based on the crystal structure. Note that the acidic phenol group has donated a proton to the basic pyridine group to form a zwitterion, and the hydroxymethyl group has reacted with the aldehyde group to form a hemiacetal.
Names
	Preferred IUPAC name 3-Hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde
Identifiers
CAS Number	66-72-8 ; 65-22-5 (hydrochloride) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17310 ;
ChEMBL	ChEMBL102970 ;
ChemSpider	1021 ;
DrugBank	DB00147 ;
ECHA InfoCard	100.000.573
KEGG	C00250 ;
PubChem CID	1050;
UNII	3THM379K8A ; 1416KF0QBC (hydrochloride) ;
CompTox Dashboard (EPA)	DTXSID4046020 ;
	InChI InChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,4,10,12H,3H2,1H3 Key: RADKZDMFGJYCBB-UHFFFAOYSA-N ; 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;
	SMILES O=Cc1c(O)c(C)ncc1CO;
Properties
Chemical formula	C8H9NO3
Molar mass	167.16 g/mol
Melting point	165 °C (329 °F; 438 K) (decomposes)
Related compounds
Related arylformaldehydes	Damnacanthal; Gossypol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Pyridoxal (PL)^[3] is one form of vitamin B₆.

Some medically relevant bacteria, such as those in the genera Granulicatella and Abiotrophia, require pyridoxal for growth. This nutritional requirement can lead to the culture phenomenon of satellite growth. In in 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 the Great Oxidation Event.^[4]

References

^ "CSD Entry: BIHKEI01". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. 1985. Archived from the original on 2023-11-04. Retrieved 2023-11-04.
^ 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.
^ "Vitamin B-6". iupac.qmul.ac.uk. Retrieved 2024-09-26.
^ "Protein Domain Structure Uncovers the Origin of Aerobic Metabolism and the Rise of Planetary Oxygen", Gustavo Caetano-Anolles et al., published in Structure; paper available from University of Illinois News Bureau, 2012.

[BIHKEI01-1] "CSD Entry: BIHKEI01". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. 1985. Archived from the original on 2023-11-04. Retrieved 2023-11-04.

[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. Retrieved 2024-09-26.

[4] "Protein Domain Structure Uncovers the Origin of Aerobic Metabolism and the Rise of Planetary Oxygen", Gustavo Caetano-Anolles et al., published in Structure; paper available from University of Illinois News Bureau, 2012.

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See also

References