7982. Pyridoxine Hydrochloride

Nomenclature

CAS number: 58-56-0
5-Hydroxy-6-methyl-3,4-pyridinedimethanol hydrochloride; pyridoxol hydrochloride; vitamin B6 hydrochloride; pyridoxinium chloride; adermine hydrochloride; 2-methyl-3-hydroxy-4,5-bis(hydroxymethyl)pyridine hydrochloride; 5-hydroxy-6-methyl-3,4-pyridinedicarbinol hydrochloride; 3-hydroxy-4,5-dimethylol-α-picoline hydrochloride; Bonasanit (Weimer); Hexabione hydrochloride; Hexabetalin; Hexavibex (Parke-Davis); Pyridipca; Pyridox (Oxford); Bécilan; Benadon (Roche); Hexermin; Campoviton 6; Hexobion (Merck KGaA).
C8H12ClNO3; mol wt 205.64.
C 46.73%, H 5.88%, Cl 17.24%, N 6.81%, O 23.34%.

Description and references

One of the vitamins of the B6 complex; see also Codecarboxylase; Pyridoxal; Pyridoxamine Dihydrochloride. Present in many foodstuffs; esp good sources are yeast, liver and cereals. Isoln: Keresztesy, Stevens, Proc. Soc. Exp. Biol. Med. 38, 64 (1938); Gy"orgy, J. Am. Chem. Soc. 60, 983 (1938); Kuhn, Wendt, Ber. 71, 780, 1118 (1938). Structure: E. T. Stiller et al., J. Am. Chem. Soc. 61, 1237 (1939); R. Kuhn et al., Ber. 72, 305 sqq. (1939). uv absorption spectrum: E. A. Peterson, H. A. Sober, J. Am. Chem. Soc. 76, 169 (1954). Synthesis: Harris, Folkers, J. Am. Chem. Soc. 61, 1242, 1245, 3307 (1939); P. G. Stevens, US 2680743 and US 2734063 (1954, 1956 both to Gen. Aniline); P. I. Pollak, US 2904551, US 3024244, US 3024245 (1959, 1962, 1962 all to Merck & Co.); E. E. Harris et al., J. Org. Chem. 27, 2705 (1962); W. B"oll, H. K"onig, Ann. 1979, 1657; T. Shono et al., Chem. Lett. 1981, 1121. Biosynthesis: Hiel, Spenser, Science 169, 773 (1970). Review: The Vitamins vol. 2, W. H. Sebrell, R. S. Harris, Eds. (Academic, New York, 2nd ed., 1968) pp 1-117.

Chemical structure

Properties

Platelets or thick, birefringent rods from alcohol + acetone. Reasonably stable to light and air. Dec 205-212°. Sublimes. (Free base, mp 160°.) uv max (0.1N HCl): 290 nm (ε 8400); (phosphate buffer, pH 7): 253, 325 nm (ε 3700, 7100). One gram dissolves in about 4.5 ml water, 90 ml alcohol. Sol in propylene glycol. Sparingly sol in acetone. Insol in ether, chloroform. pH of a 10% w/v soln in water: 3.2. Acidic aq solns are stable and may be heated for 30 min at 120° without decompn.

Therapeutic Category

Vitamin (enzyme cofactor).

Therapeutic Category (Veterinary)

Nutritional factor.

Keywords

Enzyme Cofactor; Vitamin/Vitamin Source; Vitamin B6