ChemicalBook Product Catalog Analytical Chemistry Standard Analytical Standards 2,6-diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one

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

2,6-diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one Basic information
Product Name:2,6-diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one
Synonyms:2,6-Diamino-5-(β-D-glucopyranosyloxy)pyrimidin-4-ol;Divicine β-D-glucopyranoside;Vicine【phytotoxin】;Vicioside;VICINE(SH);2,6-Diamino-5-(beta-D-glucopyranosyloxy)-4(1H)-pyrimidinone;Divicine beta-D-glucopyranoside;NSC 95092
CAS:152-93-2
MF:C10H16N4O7
MW:304.26
EINECS:205-809-4
Product Categories:
Mol File:152-93-2.mol
2,6-diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one Structure
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)
pka9.56±0.50(Predicted)
form neat
BRN 44407
Stability:Hygroscopic
Safety Information
WGK Germany 3
MSDS Information
2,6-diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one Usage And Synthesis
UsesVicine 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)
DefinitionChEBI: Vicine is a glycoside.
Purification MethodsCrystallise 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.]
2,6-diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one Preparation Products And Raw materials
Daurinoline Xanthiazone veratramine VERATRIDINE Xanthiside L-Hyoscyamine daurisoline Diphenhydramine Stevioside 2-[2-(Methylamino)benzoyl]-3,4-dihydro-β-carboline-1(2H)-one VERATRINE menisdaurin 4-Hydroxypyrimidine 2,6-diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one
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