References of Thiazolium,3-[(1,6-dihydro-2-methyl-6-oxo-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-,chloride (1:1)
Title: Oxythiamine
CAS Registry Number: 582-36-5
CAS Name: 3-[(1,4-Dihydro-2-methyl-4-oxo-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methylthiazolium chloride
Synonyms: 5-(2-hydroxyethyl)-3-[(4-hydroxy-2-methyl-5-pyrimidinyl)methyl]-4-methylthiazolium chloride
Molecular Formula: C12H16ClN3O2S
Molecular Weight: 301.79
Percent Composition: C 47.76%, H 5.34%, Cl 11.75%, N 13.92%, O 10.60%, S 10.62%
Literature References: Prepn: F. Bergel, A. R. Todd,
J. Chem. Soc. 1937, 1504; M. Soodak, L. R. Cerecedo,
J. Am. Chem. Soc. 66, 1988 (1944). Improved prepn: H. N. Rydon,
Biochem. J. 48, 383 (1951). Thiamine antagonist activity: A. J. Eusebi, L. R. Cerecedo,
Science 110, 162 (1949); L. J. Daniel, L. C. Norris,
Proc. Soc. Exp. Biol. Med. 72, 165 (1949); and distribution in tissues: C. J. Gubler, D. S. Murdock,
J. Nutr. Sci. Vitaminol. 28, 217 (1982). Proposed mechanism of action: S. A. Strumilo
et al., Biomed. Biochim. Acta 43, 159 (1984). Determn by HPLC: B. C. Hemming, C. J. Gubler,
J. Liq. Chromatogr. 3, 1697 (1980).
Derivative Type: Hydrochloride
Molecular Formula: C12H16ClN3O2S.HCl
Molecular Weight: 338.25
Percent Composition: C 42.61%, H 5.07%, Cl 20.96%, N 12.42%, O 9.46%, S 9.48%
Properties: Flat needles grouped in rosettes, dec 195°. uv max (acid soln): 265, 258, 228, 223 nm; (alkaline soln): 268, 260, 228, 221 nm. Does not give the thiochrome reaction.
Absorption maximum: uv max (acid soln): 265, 258, 228, 223 nm; (alkaline soln): 268, 260, 228, 221 nm
Derivative Type: Diphosphate
Properties: Crystals, mp 127-129°.
Melting point: mp 127-129°
Derivative Type: Monophosphoric acid ester
Properties: Hygroscopic crystals, dec 185-186°.
Derivative Type: Triphosphoric acid ester
Properties: Minute crystals, dec 245-255°.