Galactoflavin

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Galactoflavin
Names
IUPAC name
7,8-Dimethyl-10-[(2S,3R,4S,5R)-2,3,4,5,6-pentahydroxyhexyl]benzo[g]pteridine-2,4-dione
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C18H22N4O7/c1-7-3-9-10(4-8(7)2)22(5-11(24)14(26)15(27)12(25)6-23)16-13(19-9)17(28)21-18(29)20-16/h3-4,11-12,14-15,23-27H,5-6H2,1-2H3,(H,21,28,29)/t11-,12+,14+,15-/m0/s1
    Key: RPADDAUXKBBASM-MXYBEHONSA-N
  • CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)C[C@@H]([C@H]([C@H]([C@@H](CO)O)O)O)O
Properties
C18H22N4O7
Molar mass 406.395 g·mol−1
Appearance Yellow solid
Melting point 260 °C (500 °F; 533 K) (dec)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Galactoflavin is a synthetic compound and riboflavin (vitamin B2) antagonist and antimetabolite. It is a biochemical tool used primarily in research to induce riboflavin deficiency in animal models and humans. It is structurally similar to riboflavin, where the ribose-derived side chain is replaced by a galactose-derived group.

Galactoflavin's chemical formula is C18H22N4O7 and has a molecular weight of 406.40 g/mol. Galactoflavin appears as yellow crystals that decompose at 260 °C and exhibit absorption maxima at 223, 267, 370, and 445 nm.[1] It displays yellow-green fluorescence in water.[1]

Biological activity

Research uses

References

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