Xanthine Chemical Properties

Melting point:

300 °C

Boiling point:

274.55°C (rough estimate)

Density 

1.5452 (rough estimate)

vapor density 

5.3 (vs air)

refractive index 

1.8500 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

NH₄OH: freely soluble

pka

pKa 9.95 (Uncertain)

form 

Powder

color 

White to slightly yellow

Odor

Odorless

Water Solubility 

Soluble in water(0.067g/L).

Merck 

14,10059

BRN 

8733

InChIKey

LRFVTYWOQMYALW-UHFFFAOYSA-N

LogP

-0.730

CAS DataBase Reference

69-89-6(CAS DataBase Reference)

NIST Chemistry Reference

Xanthine(69-89-6)

EPA Substance Registry System

Xanthine (69-89-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36-43-36/37/38

Safety Statements 

36/37-37/39-26

WGK Germany 

3

RTECS 

ZD7700000

TSCA 

Yes

HS Code 

29335990

MSDS

• Language:English Provider:2,6-Dihydroxypurine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Xanthine Usage And Synthesis

Chemical Properties

White to off-white crystalline powder

Uses

2,6-Dihydroxypurine was fund in animal organs, yeast, patatoes, coffee beans, tea. 2,6-Dihydroxypurine can be used to relax and widen certain breathing passages of the lungs. It is also found that a large number of derivatives have adenoside receptor antagonist properties.

Uses

Xanthine and xanthine oxidase system can be used to produce superoxide radicals.

Definition

A poisonous colorless crystalline organic compound that occurs in blood, coffee beans, potatoes, and urine. It is used as a chemical intermediate.

Definition

Xanthine: a purine base, C₅H₄N₄O₂,found in many organisms.

Origin

Xanthines (1H-purine-2,6(3H,7H)-diones) are purine based natural heterocyclic alkaloids. They were first discovered in 1817 by German chemist Emil Fisher and later the name ‘xanthine’ was coined in 1899[1].

Biological Functions

In fact, xanthine and its derivatives act as intermediate molecules in generation of GMP, GDP and GTP via the salvage pathway inside the cells. In addition, xanthine plays imperative role in catabolism of nucleotides and nucleic acids as xanthine acts as precursor of uric acid. Therefore, xanthine contains similar skeleton as that of purines which forms the building blocks of unit of life i.e. ribonucleotides (RNA) and deoxyribonucleotides (DNA). The structural resemblance with two of the important purine derivatives Adenine and Guanine; makes xanthine a good therapeutic molecule[1].

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 22, p. 1200, 1974 DOI: 10.1248/cpb.22.1200

General Description

Xanthine is a purine that can be produced in the purine metabolic pathway via different precursors:

• Guanine deamination by guanine deaminase
• Hypoxanthine conversion by xanthine oxidoreductase

Biochem/physiol Actions

A high level of xanthine is implicated in metabolic disorders like Lesch-Nyhan syndrome. A xanthine-based biosensor may be useful for detecting xanthine in food and clinical samples. Blood and urine samples of patients with renal failure, gout and xanthinuria show high levels of xanthine.

Purification Methods

The monohydrate separates in a microcrystalline form on slow acidification with acetic acid of a solution of xanthine in dilute NaOH. It is also precipitated by addition of conc NH3 to its solution in hot 2N HCl (charcoal). After washing with H2O and EtOH, it is dehydrated by heating above 125o. Its solubility in H2O is 1 in 14,000parts at 16o and 1 in 1,500parts of boiling H2O, and separates as plates . It has no m, but the perchlorate has m 262-264o [Lister Purines Part II, Fused Pyrimidines Brown Ed, Wiley-Interscience pp252-253 1971, ISBN 0-471-38205-1]. [Beilstein 26 H 447, 26 I 131, 26 II 260, 26 III/IV 2327.]

References

[1] Ahlawat, Jyoti Minakshi Sharma and Chandra S. Pundir. “Advances in xanthine biosensors and sensors: A review.” Enzyme and Microbial Technology 69 1 (2023).

Xanthine(69-89-6)Related Product Information

• XANTHOSINE
• Diprophylline
• 8-Bromotheophylline
• 3-ISOBUTYL-1-METHYLXANTHINE
• ISOCAFFEINE
• Aminophylline
• 7-METHYLXANTHINE
• CAFFEINE
• PROXYPHYLLINE
• XANTHOSINE 5'-MONOPHOSPHATE DISODIUM SALT
• 7-(2-CHLOROETHYL)THEOPHYLLINE
• Theophylline-7-acetic acid
• 3-Methylxanthine
• 1,7-DIMETHYLXANTHINE
• 8-Aza-2,6-dihydroxypurine, Semihydrate, 3H-1,2,3-Triazolo(4,5-d)pyrimidine-5,7-diol
• 3-METHYL-7-PROPYL-2,6-DIHYDROXYPURINE
• 2,6-DIHYDROXYPURINE SODIUM SALT
• Oxipurinol