2,6-diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one Chemical Properties

Melting point:

242-244℃

alpha 

D26 -11.7° (c = 3.9 in 0.2N NaOH)

Boiling point:

445.09°C (rough estimate)

Density 

2.18

refractive index 

1.6200 (estimate)

solubility 

Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)

pka

9.56±0.50(Predicted)

BRN 

44407

Stability:

Hygroscopic

Safety Information

WGK Germany 

3

2,6-diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one Usage And Synthesis

Uses

Vicine is a pyrimidine glycosides, a precursor of the aglycons divicine and isouramil which is main factors of favism. It is found in faba/fava bean. Also, it is derived from Ethyl Glyoxylate (E918550), which is used as a reagent in the synthesis of a new class of cinnamyl-triazole compounds which can be used as selective inhibitors of human aromatase (cytochrome P 450 19A1)

Definition

ChEBI: Vicine is a glycoside.

Purification Methods

Crystallise Vicine from water (1%) or aqueous 85% EtOH, and dry it at 135o. [Bendich & Clements Biochim Biophys Acta 12 462 1953, Beilstein 31 H 163, 2 5 III/IV 4285.]

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