Isoalloxazine

Structural formula
General
Surname	Isoalloxazine
other names	(3 H , 10 H ) -Benzo [ g ] pteridine-2,4-dione
Molecular formula	C 10 H 6 N 4 O 2
Brief description	yellow solid
External identifiers / databases
CAS number 490-59-5 EC number 207-714-3 ECHA InfoCard 100.007.014 PubChem 5372720 ChemSpider 4522915 Wikidata Q408840
properties
Molar mass	214.18 g mol −1
Physical state	firmly
solubility	almost insoluble in water, dilute acids and ethanol bad in DMSO and diluted alkalis
safety instructions
GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Isoalloxazine is a chemical compound from the group of heterocycles . It is derived from pteridine by adding another ring. Isoalloxazine forms yellow-green crystals, the solutions of which are highly fluorescent .

The isoalloxacin ring system is an important structural element of the flavins and occurs e.g. B. in riboflavin or in the coenzymes FAD and FMN .

Manufacturing

Isoalloxazines are easily accessible synthetically via uracil derivatives. The following figure shows a simple synthesis route:

The isomer of isoalloxazine is alloxazine, (1 H , 3 H ) -Benzo [ g ] pteridine-2,4-dione, which is very similar in its properties to isoalloxazine, but is of far less importance:

Individual evidence

1. ↑ ^{a b c} data sheet isoalloxazine from Sigma-Aldrich , accessed on June 13, 2011 ( PDF ).
2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
3. ^ A. Tölpel: Chemistry and Physics of Milk: Natural Material - Raw Material - Food , Behr Verlag, 2004, 3rd edition, p. 351. ISBN 3-89947-131-8 .
4. ↑ Fumio Yoneda, Yoshiharu Sakuma, Misuzu Ichiba, Kazuko Shinomura: Syntheses of isoalloxazines and isoalloxazine 5-oxides. A new synthesis of riboflavin , in: J. Am. Chem. Soc. , 1976 , 98  (3), pp. 830-835; doi : 10.1021 / ja00419a034 .