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Xanthine

Xanthine Structure
CAS No.
69-89-6
Chemical Name:
Xanthine
Synonyms
XANTHINE;Xan;Xanthin;ISOXANTHINE;3,7-Dihydro-1H-purine-2,6-dione;7H-xanthine;9H-PURINE-2,6-DIOL;1H-Purine-2,6(3H,7H)-dione;Xanthione;usafcb-17
CBNumber:
CB0197999
Molecular Formula:
C5H4N4O2
Molecular Weight:
152.11
MOL File:
69-89-6.mol
MSDS File:
SDS
Modify Date:
2024/5/23 13:57:25

Xanthine 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
form Powder
pka pKa 9.95 (Uncertain)
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

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H317-H319
Precautionary statements  P280-P305+P351+P338
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
NFPA 704
1
2 0

Xanthine price More Price(19)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) X7375 Xanthine ≥99% 69-89-6 10G ₹6748.8 2022-06-14 Buy
Sigma-Aldrich(India) X7375 Xanthine ≥99% 69-89-6 25G ₹14840.7 2022-06-14 Buy
Sigma-Aldrich(India) X7375 Xanthine ≥99% 69-89-6 100G ₹40759.2 2022-06-14 Buy
Sigma-Aldrich(India) X4002 Xanthine BioUltra, ≥99% 69-89-6 1G ₹8003.1 2022-06-14 Buy
Sigma-Aldrich(India) X4002 Xanthine BioUltra, ≥99% 69-89-6 5G ₹15573.3 2022-06-14 Buy
Product number Packaging Price Buy
X7375 10G ₹6748.8 Buy
X7375 25G ₹14840.7 Buy
X7375 100G ₹40759.2 Buy
X4002 1G ₹8003.1 Buy
X4002 5G ₹15573.3 Buy

Xanthine Chemical Properties,Uses,Production

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.

Definition

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

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].

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

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).

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