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Xanthine

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
MDL Number:
MFCD00078453
MOL File:
69-89-6.mol
MSDS File:
SDS
Last updated:2024-05-15 13:17:26

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)
EWG's Food Scores 1
FDA UNII 1AVZ07U9S7
NIST Chemistry Reference Xanthine(69-89-6)
EPA Substance Registry System Xanthine (69-89-6)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
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(43)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich X0626 Xanthine ≥99.5% (HPLC), purified by recrystallization 69-89-6 5g $94.6 2024-03-01 Buy
TCI Chemical X0004 Xanthine >98.0%(HPLC) 69-89-6 25g $65 2024-03-01 Buy
Alfa Aesar A11077 Xanthine, 99% 69-89-6 25g $84 2024-03-01 Buy
Alfa Aesar A11077 Xanthine, 99% 69-89-6 100g $207.65 2024-03-01 Buy
Sigma-Aldrich X7375 Xanthine ≥99% 69-89-6 10g $73.4 2024-03-01 Buy
Product number Packaging Price Buy
X0626 5g $94.6 Buy
X0004 25g $65 Buy
A11077 25g $84 Buy
A11077 100g $207.65 Buy
X7375 10g $73.4 Buy

Xanthine Chemical Properties,Uses,Production

Chemical Properties

White to off-white crystalline powder

Uses

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

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

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

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].

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).

2969-81-5
76194-10-0
69-89-6
Synthesis of Xanthine from Ethyl 4-bromobutyrate and Formamide, N-(6-amino-1-butyl-1,2,3,4-tetrahydro-2,4-dioxo-5-pyrimidinyl)-
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View Lastest Price from Xanthine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2,6-Dihydroxypurine pictures 2024-05-16 2,6-Dihydroxypurine
69-89-6
US $9.90 / kg 1kg 99% 2000kg hebei hongtan Biotechnology Co., Ltd
2,6-Dihydroxypurine pictures 2024-05-16 2,6-Dihydroxypurine
69-89-6
US $80.00 / kg 1kg 99.9% 1000 hebei hongtan Biotechnology Co., Ltd
2,6-Dihydroxypurine pictures 2024-05-15 2,6-Dihydroxypurine
69-89-6
US $0.00-0.00 / kg 1kg 0.99 50000kg Hebei Kingfiner Technology Development Co.Ltd
2,6-DIOXOPURINE 2,6-DIOXYPURINE 2,6-DIHYDROXYPURINE PURINE-2,6(1H,3H)-DIONE TIMTEC-BB SBB004054 UREOUS ACID 3,7-dihydro-1h-purine-6-dione 1H-Purine-2,6-diol 1H-Purine-2,6-dione, 3,7-dihydro- 2,6(1,3)-Purinedion 2,6-Dioxo-1,2,3,6-tetrahydropurine 2,6-Dixoxpurine purine-2(3H),6(1H)-dione xanthine 99-100% xanthine sigmaultra 2,6-DihydroxyPurine(Xanthine) XanthineForBiochemistry Lutein(MarigoldP.E)5%,20%ByHplc Xanthine, 98+% Xanthine,99% 2,6[1,3]-Purinedione 2,6-dihydroxypurin Xanthione XANTHINE OR 2,6-DIHYDROXYPURINE XANTHINE(RG) Xanthine (2,6-Dihydroxypurine) 2,6-Dihydropurine 2,6(1H,3H)purinedione 6-dione,3,7-dihydro-1H-Purine-2 9h-purine-2,6-(1h,3h)-dione 9H-Purine-2,6(1H,3H)-dione Dioxopurine Pseudoxanthine Purine-2,6-diol USAF CB-17 usafcb-17 Xanthic oxide xanthicoxide XANTHINE extrapure CHR 3,9-Dihydropurine-2,6-dione H,3H,7H-Xanthine 1H-Purine-2,6-dione XANTHINEANALYTICAL GRADE 3,7-Dihydroxy-1H-purine-2,6-dione 2,3,6,7-tetrahydro-1H-purine-2,6-dione Xanthine, 98% 25GR Xanthine, 98% 5GR 1H,3H,7H-Xanthine 1H,3H,9H-Xanthine 9H-xanthine 3,7-dihydropurine-2,6-dione Xanthine, ≥99.5%(HPLC) ,6-Dihydroxypurine Xanthine - CAS 69-89-6 - Calbiochem 7H-purine-2,6-diol JACS-69-89-6 Xanthine, 99%, for bio 1H-Purine-2,6-dione, 3,9-dihydro-