ISOXANTHOPTERIN Property

Melting point:

>300 °C

Density 

2.17±0.1 g/cm3(Predicted)

storage temp. 

room temp

solubility 

DMSO (Very Slightly)

pka

11.32±0.20(Predicted)

form 

powder

color 

off-white

BRN 

181594

LogP

-3.760 (est)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

RTECS 

UO3425000

F 

10-23

HS Code 

29335990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

ISOXANTHOPTERIN Chemical Properties,Usage,Production

Chemical Properties

Off-white powder

Uses

Isoxanthopterin is a substrate for the enzyme isoxanthopterin deaminase.

Definition

ChEBI: 2-aminopteridine-4,7-diol is a dihydroxypteridine.

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 4450, 1953 DOI: 10.1021/ja01114a016

Biological Activity

isoxanthopterin interferes with rna and dna synthesis.isoxanthopterin, a natural intermediate in the pteridine pathway, plays critical roles in pigmentation and cell division.

in vitro

isoxanthopterin was identified as a pteridine of wide natural occurrence and was reported to exerts an inhibitory action on the synthesis of ribosomal rna, possibly soluble rna and on dna in developing eggs of the milkweed bug oncopeltus fasciatus. such effects were measured by partially incubating dechorionated eggs in a solution containing isoxanthopterin and radioactive uridine or thymidine, and then testing the incorporation of the isotope into ribosomal rna or dna. the detailed mechanism of this inhibition had been discussed, and the tentative conclusion was agreed that it was due to an interaction between the pteridine and the nucleic acid (most probably dna) [1].

in vivo

previous animal study showed that rats with inherited retinal dystrophy appeared to differ from healthy rats by an elevated isoxanthopterin excretion in urine. rcs rats responded to feeding of monapterin with an increase of isoxanthopterin excretion. this phenomenon supported the idea that the rcs rat had an increased xanthinoxidase activity compared with healthy rats [2].

Purification Methods

Purify it by repeated precipitation from alkaline solution with acid (preferably AcOH or formic acid), filter, wash well with H2O, then EtOH and dry at 100o. The purity is checked by paper chromatography [RF 0.15 (n-BuOH/AcOH/H2O, 4:1:1); 0.33 (3% aqueous NH4OH). [Goto et al. Arch Biochem Biophys 111 8 1965.] [For biochemistry see Blakley Biochemistry of Folic Acid and Related Pteridines North Holland Publ Co, Amsterdam 1969.] [Beilstein 26 III/IV 3999.]

References

[1] lagowski, j. m. and forrest, h.s. interaction in vitro between isoxanthopterin and dna. proceedings of the national academy of sciences of the united states of america 58(4), 1541-1547 (1967).
[2] g. cremer-bartels, h. gerding, l. hanneken and k. krause. isoxanthopterin excretion of rats with inherited retinal dystrophy. pteridines vol. 2, 1990, pp. 103 -105.