6-Hydroxypurine Chemical Properties

Melting point:

>300 °C (lit.)

Boiling point:

250.36°C (rough estimate)

Density 

1.4295 (rough estimate)

refractive index 

1.8500 (estimate)

storage temp. 

2-8°C

solubility 

1 M NaOH: 25 mg/mL

form 

powder

pka

8.7(at 25℃)

color 

Colorless to yellow to brown, darken on storage with no loss of purity

Odor

Odorless

Water Solubility 

practically insoluble

Merck 

14,4869

BRN 

5811

InChIKey

FDGQSTZJBFJUBT-UHFFFAOYSA-N

LogP

-0.910 (est)

CAS DataBase Reference

68-94-0(CAS DataBase Reference)

NIST Chemistry Reference

Hypoxanthine(68-94-0)

EPA Substance Registry System

Hypoxanthine (68-94-0)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-22-40

Safety Statements 

22-24/25-37/39-26-36

WGK Germany 

3

RTECS 

UP0791000

Hazard Note 

Harmful

TSCA 

Yes

HS Code 

29335990

Toxicity

LD50 intraperitoneal in mouse: 750mg/kg

MSDS

• Language:English Provider:6-Hydroxypurine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

6-Hydroxypurine Usage And Synthesis

Description

Hypoxanthine is a naturally occurring purine derivative and intermediate in the synthesis of uric acid. It is elevated in the spinal fluid of patients with Lesch-Nyhan syndrome, a metabolic disorder whose symptoms include cerebral palsy, cognitive deficits, motor dysfunction, self-mutilation, and hyperuricemia. Injection of hypoxanthine (10 μM) increases succinate dehydrogenase and complex II activities and decreases cytochrome c oxidase activity, resulting in neuroenergetic impairment, ATP depletion, and cellular apoptosis in rat striatum. It is also used to induce hyperuricemia in mice for use in the development of hypouricemic agents.

Chemical Properties

White to off-white powder

Uses

A naturally occurring purine derivative. Pharmaceuticals, Intermediates & Fine Chemicals

Uses

Hypoxanthine is a nutrient additive for a variety of cell culture applications involving bacterial, parasite (Plasmodium falciparum) and animal cells. Hypoxanthine is a component of selection media used in hybridoma technologies.

Uses

Hypoxanthine, is used as a marker for energy perturbation in hypoxia/ ischemia. The compound has been used in studies as in indicator, along with uric acid and allantoin , of in vivo free radical reactions. It has been also used in DNA studies to investigate the destabilizing effect it has on DNA duplexes containing hypoxanthine as a base, in a gas phase versus a liquid phase. Hypoxanthine has also been used in studies along with 8-oxoguanine nucleotides to investigate their interaction with human DNA pol ? (DNA polymerase alpha) and DNA polymerase I from Bacillus stearothermophilus. It is also used as a pharmaceutical intermediate.

Definition

ChEBI: A purine nucleobase that consists of purine bearing an oxo substituent at position 6.

General Description

Hypoxanthine (6-hydroxypurine), a purine derivative is a naturally occurring compound. It is the deaminated form of adenine and a breakdown product of adenosine monophosphate (AMP).

Biochem/physiol Actions

Hypoxanthine?is capable of stimulating cell death. It can also induce reactive oxygen species (ROS). It results in endothelial dysfunction via apoptosis, stimulated by oxidative stress.

Safety Profile

Moderately toxic by intraperitoneal route. An experimental teratogen. When heated to decomposition it emits toxic fumes of Nox

Purification Methods

Crystallise it from hot water and dry it at 105o. [Beilstein 26 II 252, 26 III/IV 2081.]

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