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ISOXANTHOPTERIN

CAS No.
529-69-1
Chemical Name:
ISOXANTHOPTERIN
Synonyms
Mesopterin;Ranachrome 4;ISOXANTHOPTERIN;isoxanthopterine;ISOXANTHOPTERIN 98+%;Isoxanthopterin ,97%;2-aminopteridine-4,7-diol;2-Amino-4,7-pteridinediol;ISOXANTHOPTERIN USP/EP/BP;ISOXANTHOPTERIN APPROX. 99%
CBNumber:
CB9734674
Molecular Formula:
C6H5N5O2
Molecular Weight:
179.14
MDL Number:
MFCD00006696
MOL File:
529-69-1.mol
MSDS File:
SDS
Last updated:2023-05-25 18:01:24

ISOXANTHOPTERIN Properties

Melting point >300 °C
Density 2.17±0.1 g/cm3(Predicted)
storage temp. room temp
solubility DMSO (Very Slightly)
form powder
pka 11.32±0.20(Predicted)
color off-white
BRN 181594
LogP -3.760 (est)
FDA UNII XR11PF6TYR

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319
Precautionary statements  P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  22-24/25-36-26
WGK Germany  3
RTECS  UO3425000
10-23
HS Code  29335990

ISOXANTHOPTERIN price More Price(19)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 17564 Isoxanthopterin ≥95% 529-69-1 10mg $37 2024-03-01 Buy
Cayman Chemical 17564 Isoxanthopterin ≥95% 529-69-1 50mg $108 2024-03-01 Buy
Cayman Chemical 17564 Isoxanthopterin ≥95% 529-69-1 100mg $178 2024-03-01 Buy
TRC I918343 Isoxanthopterin 529-69-1 2.5mg $50 2021-12-16 Buy
Biosynth Carbosynth FI08026 Isoxanthopterin 529-69-1 25mg $52.5 2021-12-16 Buy
Product number Packaging Price Buy
17564 10mg $37 Buy
17564 50mg $108 Buy
17564 100mg $178 Buy
I918343 2.5mg $50 Buy
FI08026 25mg $52.5 Buy

ISOXANTHOPTERIN Chemical Properties,Uses,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.

3254-85-1
529-69-1
Synthesis of ISOXANTHOPTERIN from 2-amino-3,4,7,8-tetrahydro-4,7-dioxo-6-Pteridinecarboxylic acid

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2-amino-4,7(1h,8h)-pteridinedione 2-amino-4,7(3h,8h)-pteridinedione 8h)-pteridinedione,2-amino-7(1h 8h)-pteridinedione,2-amino-7(3h ISOXANTHOPTERIN 2-AMINO-4,7-DIHYDROXY-1,3,5,8-TETRAAZANAPHTHALENE 2-AMINO-4,7-DIHYDROXYPTERIDINE 2-aminopteridine-4,7-diol isoxanthopterine ISOXANTHOPTERIN APPROX. 99% ISOXANTHOPTERIN 98+% 2-amino-1,8-dihydropteridine-4,7-dione 4,7(1H,8H)-Pteridinedione,2-amino-(9CI) 2-AMINOPTERIDINE-4,7(1H,8H)-DIONE 2-amino-1,8-dihydropteridine-4,7-quinone 2-azanyl-1,8-dihydropteridine-4,7-dione Isoxanthopterin ,97% Isoxanthopterin,2-Amino-4,7-dihydroxy-1,3,5,8-tetraazanaphthalene, 2-Amino-4,7-dihydroxypteridine, 2-Amino-4,7-pteridinediol 2-Amino-4,7-dihydroxy-1,3,5,8-tetraazanaphthalene, 2-Amino-4,7-dihydroxypteridine, 2-Amino-4,7-pteridinediol Mesopterin Ranachrome 4 2-Amino-4,7-pteridinediol 4,7(3H,8H)-Pteridinedione, 2-amino- ISOXANTHOPTERIN USP/EP/BP 529-69-1 C6H5N5O2 Nucleoside Analogs Nucleosides, Nucleotides, Oligonucleotides Biochemicals and Reagents BioChemical PIPERIDINE