9297. Thiamine Disulfide

Nomenclature

CAS number: 67-16-3
N,N′-[Dithiobis[2-(2-hydroxyethyl)-1-methyl-2,1-ethenediyl]]bis[N-[(4-amino-2-methyl-5-pyrimidinyl)methyl]formamide]; aneurin disulfide; vitamin B1 disulfide; Aktivin (Kobayashi); Neolamin (Nippon Kayaku).
C24H34N8O4S2; mol wt 562.71.
C 51.23%, H 6.09%, N 19.91%, O 11.37%, S 11.40%.

Description and references

Isoln: Zima, Williams, Ber. 73, 941 (1940). Prepn: Warnat, US 2458453 (1949 to Hoffmann-La Roche); Matsukawa, Hirano, J. Pharm. Soc. Jpn. 73, 379 (1953); Hirano, Iwatsu, ibid. 73, 1115 (1953); Kawasaki, ibid. 76, 706 (1956). Bioavailability: N. Aoyagi et al., Chem. Pharm. Bull. 34, 281 (1986).

Chemical structure

Properties

When anhydr, mp 177° with intense yellow coloration. Very sparingly sol in benzene, acetone, ether, ethanol; freely sol if the crystals contain solvated acetone or water. Soly in water at 37° (mg/ml): 37.7 (pH 1.2); 3.0 (pH 3); 1.33 (pH 5); 0.568 (pH 7.2).

Derivative

Hydrochloride.

Nomenclature

CAS number: 18642-10-9

Properties

Crystals from methanol + water, dec 231°.

Derivative

Phosphate.

Nomenclature

CAS number: 992-46-1
Thiamine monophosphate disulfide; Biotinin (Sankyo); Vitamogen (Tanabe).
C24H36N8O10P2S2; mol wt 722.67.
C 39.89%, H 5.02%, N 15.51%, O 22.14%, P 8.57%, S 8.87%.

Derivative

O,O-Diisobutyrate.

Nomenclature

CAS number: 3286-46-2
O-Isobutyrylthiamine disulfide; bisibutiamine; sulbutiamine; Arcalion (Servier); Neodaian (Nichiiko); Vitaberin (Taisho).
C32H46N8O6S2; mol wt 702.89.
C 54.68%, H 6.60%, N 15.94%, O 13.66%, S 9.12%.

Therapeutic Category

Vitamin (enzyme cofactor).

Keywords

Enzyme Cofactor; Vitamin/Vitamin Source; Vitamin B1