Divicine

Divicine
pyrimidine tautomer
pyrimidinone tautomer
Names
IUPAC name
2,6-Diamino-4,5-dihydroxypyrimidine
Other names
2,6-Diamino-4,5-pyrimidinediol; 2,6-diamine-5-hydroxy-4(3H)-pyrimidinone; 2,4-diamino-5,6-dihydroxypyrimidine
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C4H6N4O2/c5-2-1(9)3(10)8-4(6)7-2/h9H,(H5,5,6,7,8,10) checkY
    Key: ZMWZGZSARWJATP-UHFFFAOYSA-N checkY
  • InChI=1/C4H6N4O2/c5-2-1(9)3(10)8-4(6)7-2/h9H,(H5,5,6,7,8,10)
    Key: ZMWZGZSARWJATP-UHFFFAOYAO
  • (pyrimidine tautomer): OC1=C(O)C(N)=NC(N)=N1
  • (pyrimidinone tautomer): O=C1C(O)=C(N)NC(N)=N1
Properties
C4H6N4O2
Molar mass 142.118 g·mol−1
Appearance Brownish needles
Solubility in 10% KOH Soluble[vague]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Divicine (2,6-diamino-4,5-dihydroxypyrimidine) is an oxidant and a base with alkaloidal properties found in fava beans and Lathyrus sativus. It is an aglycone of vicine. A common derivative is the diacetate form (2,6-diamino-1,6-dihydro-4,5-pyrimidinedione).[1]

  1. ^ Bendich, C. (1953). "A revision of the structural formulation of vicine and its pyrimidine aglucone, divicine". Biochim. Biophys. Acta. 12 (1–2): 462–77. doi:10.1016/0006-3002(53)90166-8. PMID 13115456.