Thiamine Diphosphate
Title: Thiamine Diphosphate
CAS Registry Number: 154-87-0
CAS Name: 3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-(4,6,6-trihydroxy-3,5-dioxa-4,6-diphosphahex-1-yl)thiazolium chloride P,P¢-dioxide
Additional Names: thiamine trihydrogen pyrophosphate (ester); cocarboxylase; thiamine pyrophosphate; thiamine diphosphate ester chloride; TDP; TPP
Trademarks: Berolase (Roche); Bivitasi (ISI); Cocalose (Maruko); Cocarvit (CT); Nutrase (Kyorin); Pyrolase (Chugai)
Molecular Formula: C12H19ClN4O7P2S
Molecular Weight: 460.77
Percent Composition: C 31.28%, H 4.16%, Cl 7.69%, N 12.16%, O 24.31%, P 13.44%, S 6.96%
Literature References: Coenzyme required for the decarboxylation of a-keto acids. Most abundant form of thiamine in animal tissues. Identification as cofactor and enzymatic synthesis: K. Lohmann, P. Schuster, Biochem. Z. 294, 183 (1937). Chemical synthesis: Weijlard, Tauber, J. Am. Chem. Soc. 60, 2263 (1938); Weil-Malherbe, Biochem. J. 34, 980 (1940); Weijlard, J. Am. Chem. Soc. 63, 1160 (1941); Karrer, Viscontini, Helv. Chim. Acta 29, 711 (1946). LC determn in blood: J. W. I. Brunnekreeft et al., J. Chromatogr. 491, 89 (1989). Role in pathogenesis of Wernicke-Korsakoff Syndrome: R. F. Butterworth et al., Alcohol. Clin. Exp. Res. 17, 1084 (1993). Review of enzyme activity: J. Ullrich et al., Vitam. Horm. 28, 365 (1970); of mechanism of action: R. Kluger, Chem. Rev. 87, 863-876 (1987); M. Louloudi, N. Hadjiliadis, Coord. Chem. Rev. 135, 429-468 (1994).
 
Derivative Type: Monohydrate
Properties: Crystals from alc contg some HCl, dec 240-244°. mp 238-240° from abs ethanol. uv max: 242 nm. Soluble in water. pH of 0.3% soln 2.23. The dry substance is very stable.
Melting point: mp 238-240° from abs ethanol
Absorption maximum: uv max: 242 nm
 
Derivative Type: Free ester tetrahydrate
Molecular Formula: C12H18N4O7P2S.4H2O
Molecular Weight: 496.37
Percent Composition: C 29.04%, H 5.28%, N 11.29%, O 35.46%, P 12.48%, S 6.46%
Literature References: Prepn: Wenz et al., US 2991284 (1961 to E. Merck).
Properties: Dec 220-225°.
 
Derivative Type: Thiamine monophosphate
CAS Registry Number: 532-40-1
CAS Name: 3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]thiazolium chloride
Additional Names: thiamine monophosphate chloride
Molecular Formula: C12H18ClN4O4PS
Molecular Weight: 380.79
Percent Composition: C 37.85%, H 4.76%, Cl 9.31%, N 14.71%, O 16.81%, P 8.13%, S 8.42%
Literature References: Prepd by sulfuric acid hydrolysis of thiamine diphosphate: Lohmann, Schuster, loc. cit.
Properties: Monohydrate; prisms from dil acetone or water, mp ~200°. Freely sol in water.
Melting point: mp ~200°
 
Therap-Cat: Vitamin (enzyme cofactor).
Keywords: Enzyme Cofactor; Vitamin/Vitamin Source; Vitamin B1.

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