763. d-Araboflavin

Nomenclature

CAS number: 5978-87-0
1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-d-arabinitol; 7,8-dimethyl-10-(arabino-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione; 6,7-dimethyl-9-d-araboflavin.
C17H20N4O6; mol wt 376.36.
C 54.25%, H 5.36%, N 14.89%, O 25.51%.

Description and references

An antagonist of riboflavine. Prepd from d-(2-amino-4,5-dimethylphenyl)arabinamine and alloxan: Kuhn, Weygand, Ber. 68, 1286 (1935); Sahashi et al., Bull. Inst. Phys. Chem. Res. (Tokyo) 24, 72 (1948), C.A. 42, 5458 (1948).

Chemical structure

Properties

Orange-yellow needles from dil acetic acid. Bitter taste, mp 302-303°. [α]D20 +78.6° (c = 0.509 in 0.1N NaOH); [α]D20 441° (c = 0.253 in 0.2N NaOH satd with borax).

Derivative

Tetraacetate.
C25H28N4O10; mol wt 544.51.
C 55.14%, H 5.18%, N 10.29%, O 29.38%.

Properties

Flat yellow prisms from ethyl acetate, mp 221-222°.