Pyridoxal 5-Phosphate
Structural Formula Vector Image
Title: Pyridoxal 5-Phosphate
CAS Registry Number: 54-47-7
CAS Name: 3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde
Additional Names: pyridoxal 5-monophosphoric acid ester; 3-hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphate; codecarboxylase
Trademarks: Pyromijin; Sechvitan; Vitazechs
Molecular Formula: C8H10NO6P
Molecular Weight: 247.14
Percent Composition: C 38.88%, H 4.08%, N 5.67%, O 38.84%, P 12.53%
Literature References: Prepn by the action of adenosine triphosphate on pyridoxal: Gunsalus et al., J. Biol. Chem. 155, 685 (1944); by the action of phosphorus oxychloride on pyridoxal in aq soln: Gunsalus et al., ibid. 161, 743 (1945); Umbreit et al., Arch. Biochem. 7, 189 (1945); by phosphorylation of pyridoxamine with 100% H3PO4 followed by oxidation: Wilson, Harris, J. Am. Chem. Soc. 73, 4693 (1951). Alternate route: Schorre, US 3124587 (1964 to E. Merck). Isoln in pure form as the oxime and as the O-methyl oxime and structure: Heyl et al., J. Am. Chem. Soc. 73, 3430 (1951). Activity as a cotransaminase in the synthesis of amino acids: Lichstein et al., J. Biol. Chem. 161, 311 (1945). Activity of natural and synthetic material: Umbreit et al., loc. cit.
Properties: Colorless in acid soln, bright-yellow in alkaline soln. uv max (alkaline soln): 390 nm (Em 3.7); in acid soln: 295 nm (Em 5.1). Gives a negative 2,6-dichloroquinone chlorimide test. On oxidation with H2O2 in alkaline solution yields [(2-methyl-3,4-dihydroxy-5-pyridyl)methyl]phosphoric acid.
Absorption maximum: uv max (alkaline soln): 390 nm (Em 3.7); in acid soln: 295 nm (Em 5.1)
Derivative Type: Oxime
CAS Registry Number: 634-25-3
Molecular Formula: C8H11N2O6P
Molecular Weight: 262.16
Percent Composition: C 36.65%, H 4.23%, N 10.69%, O 36.62%, P 11.81%
Properties: Crystals, dec 229-230°. Practically insol in water, alcohol, ether.
Derivative Type: O-Methyloxime
CAS Registry Number: 20905-71-9
Molecular Formula: C9H13N2O6P
Molecular Weight: 276.18
Percent Composition: C 39.14%, H 4.74%, N 10.14%, O 34.76%, P 11.22%
Properties: Crystals, dec 212-213°. Practically insol in water, alcohol, ether.
Derivative Type: Calcium salt
CAS Registry Number: 29956-24-9
Trademarks: Aderoxal
Properties: Yellow precipitate. Practically insol in water, alcohol or ether.
Therap-Cat: Vitamin (enzyme co-factor).
Keywords: Enzyme Cofactor; Vitamin/Vitamin Source; Vitamin B6.

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