2023. Cetotiamine

Nomenclature

CAS number: 137-76-8
Thiocarbonic acid O-ethyl ester, S-ester with N-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-N-(4-hydroxy-2-mercapto-1-methyl-1-butenyl)formamide ethyl carbonate (ester); O,S-bis(ethoxycarbonyl)thiamine; O,S-dicarbethoxythiamine; DCET.
C18H26N4O6S; mol wt 426.49.
C 50.69%, H 6.14%, N 13.14%, O 22.51%, S 7.52%.

Description and references

Prepn: Takamizawa, Hirai, Chem. Pharm. Bull. 10, 1102 (1962); Takamizawa et al., ibid. 1107; Yamamoto et al., Bitamin 25, 472 (1962), C.A. 60, 9773e (1964); GB 944641 (1963 to Shionogi).

Chemical structure

Properties

Prisms from ethyl acetate + petr ether, mp 113.5-114.5°.

Derivative

Hydrochloride monohydrate.

Nomenclature

Dicethiamin; Dicetamin (Shionogi).
C18H26N4O6S.HCl.H2O; mol wt 480.96.
C 44.95%, H 6.08%, N 11.65%, O 23.29%, S 6.67%, Cl 7.37%.

Properties

Crystals from ethyl acetate, dec 122-124°. Sol in water, methanol. Practically insol in ether, benzene.

Therapeutic Category

Vitamin B1 source.

Keywords

Enzyme Cofactor; Vitamin/Vitamin Source; Vitamin B1