Hypoxanthine

Structural formula
General
Surname	Hypoxanthine
other names	6-hydroxypurine; 1,7-dihydro-6 H -purin-6-one; Purine-6 (1 H ) -one; 9 H -purine-6-ol;
Molecular formula	C 5 H 4 N 4 O
Brief description	colorless crystals
External identifiers / databases
EC number	200-697-3
ECHA InfoCard	100,000,634
PubChem	790
ChemSpider	768
DrugBank	DB04076
Wikidata	Q410305
properties
Molar mass	136.11 g · mol -1
Physical state	firmly
Melting point	> 300 ° C
solubility	25 g · l −1 in 1M sodium hydroxide solution
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	750 mg kg −1 ( LD 50 , mouse , ip )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hypoxanthine is a naturally occurring purine derivative and formed by the action of xanthine oxidase on xanthine although the Purinabbau normally proceeds so that hypoxanthine by xanthine to xanthine oxidized is. Hypoxanthine very rarely forms the basic structure of nucleic acids . It is contained in the anticodon of tRNA in the form of the nucleoside inosine .

Occurrence

Hypoxanthine occurs, for example, in the urine in free form, as well as bound in nucleosides.

properties

The hypoxanthine molecule has several tautomers that are in equilibrium with one another:

Imine - enamine tautomerism of hypoxanthin.

Lactam - lactim -Tautomerie of hypoxanthine.

The nucleoside inosine and the nucleotide inosine monophosphate are derived from hypoxanthine .

Biological importance

Hypoxanthine is a growth factor for some microorganisms. It also contributes to the color of fish (see fish silver ). In the shell of fish swim bladders , dense layers of hypoxanthine crystallites reduce their gas permeability. The hypoxanthine oxidized at the 3-position is the frightening substance of the cypriniformes .

Historical

Hypoxanthine was discovered in the spleen and heart muscle by Josef Scherer . He described his observations in 1850.

Individual evidence

↑ Hypoxanthine data sheet at AlfaAesar, accessed on March 2, 2010 ( PDF )(JavaScript required) .

↑ ^a ^b ^c ^d Datasheet Hypoxanthine from Sigma-Aldrich , accessed on April 4, 2011 ( PDF ).

↑ Josef Scherer: About a body that occurs in the animal organism and is related to xanthicoxide . In: Friedrich Wöhler, Justus Liebig (Ed.): Annals of Chemistry and Pharmacy . tape 73 , no. 3 . Christian Friedrich Winter, 1850, ISSN 0075-4617 , p. 328–334 , doi : 10.1002 / jlac.18500730304 ( online at HathiTrunst.org ).

[alfa-1] Hypoxanthine data sheet at AlfaAesar, accessed on March 2, 2010 ( PDF )(JavaScript required) .

[Sigma-2] Datasheet Hypoxanthine from Sigma-Aldrich , accessed on April 4, 2011 ( PDF ).

[3] Josef Scherer: About a body that occurs in the animal organism and is related to xanthicoxide . In: Friedrich Wöhler, Justus Liebig (Ed.): Annals of Chemistry and Pharmacy . tape 73 , no. 3 . Christian Friedrich Winter, 1850, ISSN 0075-4617 , p. 328–334 , doi : 10.1002 / jlac.18500730304 ( online at HathiTrunst.org ).