2-Amino-4-hydroxy-1H-pteridine

2-Amino-4-hydroxy-1H-pteridine Property

Melting point:

300 °C

Boiling point:

290.2°C (rough estimate)

Density 

1.4240 (rough estimate)

refractive index 

1.9000 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Acetonitrile: Soluble
Water: Soluble

form 

powder

pka

2.27(at 20℃)

biological source

synthetic

Water Solubility 

17.54mg/L(22.5 ºC)

BRN 

150294

InChI

InChI=1S/C6H5N5O/c7-6-10-4-3(5(12)11-6)8-1-2-9-4/h1-2H,(H3,7,9,10,11,12)

InChIKey

HNXQXTQTPAJEJL-UHFFFAOYSA-N

SMILES

N1C2C(=NC=CN=2)C(=O)NC=1N

CAS DataBase Reference

2236-60-4(CAS DataBase Reference)

NIST Chemistry Reference

4(1H)-pteridinone, 2-amino-(2236-60-4)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

UO3505000

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

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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.

2-Amino-4-hydroxy-1H-pteridine Chemical Properties,Usage,Production

Chemical Properties

YELLOW-BEIGE CRYSTALLINE POWDER

Uses

Pterin is used in the biosynthesis and metabolism of tetrahydrobiopterin and molybdopterin.

Definition

ChEBI: 2-aminopteridin-4-ol is a 2-amino-4-hydroxypteridine. It is a tautomer of a 2-aminopteridin-4(3H)-one and a 2-aminopteridin-4(1H)-one.

Biological Activity

Pterine consists of pyrazine and pyrimidine with substitutions in keto and amino group. Pterine is present in all organisms including cyanobacteria. It acts as a cofactor for redox enzymes and serves as a precursor for folic acid synthesis. Pterine from the butterfly wings absorb light and elicit incoherent scattering. Pterine induces alterations in DNA by hydroxylation of deoxyguanosine.

Purification Methods

It is dissolved in hot 1% aqueous ammonia, filtered, and an equal volume of hot 1M aqueous formic acid is added. The solution is allowed to cool at 0-2o overnight. The solid is collected and washed with distilled water several times by centrifugation and dried in vacuo over P2O5 overnight, and then at 100o overnight (any ammonium formate in the sample evaporates off). [Beilstein 26 III/IV 3936.]

References

[1] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[2] RAMASAMY MAHENDRAN. Evaluation of Pterin, a Promising Drug Candidate from Cyanide Degrading Bacteria.[J]. Current Microbiology, 2018, 75 6: 684-693. DOI: 10.1007/s00284-018-1433-0
[3] SANJEEWA GAMAGEDARA  Yinfa M  Stephen Gibbons. Investigation of urinary pteridine levels as potential biomarkers for noninvasive diagnosis of cancer[J]. Clinica Chimica Acta, 2011, 412 1: Pages 120-128. DOI: 10.1016/j.cca.2010.09.015