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ALLOXAN MONOHYDRATE

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ALLOXAN MONOHYDRATE Basic information

Product Name:
ALLOXAN MONOHYDRATE
Synonyms:
  • 2,4,5,6(1H,3H)-Pyrimidinetetrone, 2,4,5,6-Tetraoxypyrimidine, 5,6-Dioxyuracil
  • 2,4,5,6-tetraoxohexahydropyrimidinehydrate
  • mesoxalylcarbamidemonohydrate
  • LABOTEST-BB LT00138148
  • MESOXALYLUREA
  • MESOXALYLUREA, MONOHYDRATE
  • 5,6-DIOXYURACIL
  • 5,6-DIOXYURACIL MONOHYDRATE
CAS:
2244-11-3
MF:
C4H4N2O5
MW:
160.09
EINECS:
607-078-0
Product Categories:
  • buildingblock
  • Pyridines, Pyrimidines, Purines and Pteredines
  • Active Pharmaceutical Ingredients
Mol File:
2244-11-3.mol
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ALLOXAN MONOHYDRATE Chemical Properties

Melting point:
255 °C (dec.)(lit.)
storage temp. 
2-8°C
solubility 
H2O: may be hazy yellow
form 
Crystalline Powder
color 
Off-white to beige-yellow
Water Solubility 
Soluble in water, ethanol, acetone, glacial acetic acid and methanol. Slightly soluble in chloroform, petroleum ether, toluene, ethyl acetate and acetic anhydride. Insoluble in ether.
Sensitive 
Air Sensitive
Merck 
14,282
BRN 
5309394
InChI
InChI=1S/C4H2N2O4.H2O/c7-1-2(8)5-4(10)6-3(1)9;/h(H2,5,6,8,9,10);1H2
InChIKey
DSXMTJRUNLATRP-UHFFFAOYSA-N
SMILES
O=C1C(NC(=O)NC1=O)=O.O
CAS DataBase Reference
2244-11-3(CAS DataBase Reference)
EPA Substance Registry System
2,4,5,6(1H,3H)-Pyrimidinetetrone, monohydrate (2244-11-3)
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Safety Information

Hazard Codes 
Xn,Xi
Risk Statements 
20/21/22-36/37/38
Safety Statements 
36-26-36/37
WGK Germany 
3
RTECS 
UW0492000
TSCA 
Yes
HS Code 
29335995

MSDS

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ALLOXAN MONOHYDRATE Usage And Synthesis

Chemical Properties

Off-white to beige-yellowish crystalline powder

Uses

specific cytotoxin (beta pacreatic cell)

Uses

Cytotoxic compound that causes oxidative base damage to nuclear DNAAlloxan monohydrate is used as a precursor to prepare purple dye murexide. It is also used in research models to induce diabetes and destroy beta cells. Further, it is a strong oxidizing agent and it forms a hemiacetal with its reduced reaction product dialuric acid.

Uses

A cytotoxic compound, Alloxan Monohydrate causes oxidative base damage to nuclear DNA.

Safety Profile

Poison by intravenous route. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

in vivo

Alloxan hydrate can be used in animal modeling to create diabetes models. Administration of Alloxan hydrate leads to a sharp increase in blood glucose levels in mice, peaking at 45 minutes. Two hours after administration, blood glucose levels decrease to near-hypoglycemic levels, reaching the lowest blood glucose level at 6 hours[3].

Induction of Diabetes[3]
Background
Alloxan hydrate induces diabetes by destroying the pancreas that produces insulin and has a toxic effect on β cells.
Specific Modeling Methods
Mice: albino NMRI ? female ? 20-25 g
Administration: 70 mg/kg ? i.v.
Note
(1) Alloxan hydrate is dissolved in hydrochloric acid (pH=5) and administered via tail vein injection within 10 minutes after dissolution.
(2) Blood sampling was done through the eye socket, with 25μL and 250μL taken to measure blood glucose and plasma insulin levels, respectively.
(3) Blood glucose and plasma insulin levels were measured using enzyme and immunoassays, respectively. Mice with blood glucose levels reaching or exceeding 200 mg/100 mL are considered diabetic.
Modeling Indicators
Molecular changes: Blood sugar levels rise, glycogen in the liver decreases, and insulin levels increase during hypoglycemia.
Correlated Product(s): Streptozotocin (HY-13753)
Opposite Product(s): /

Purification Methods

Recrystallisation from H2O gave the tetrahydrate in large prisms or rhombs. On heating at 100o, or on exposure to air, this is converted to the monohydrate. Dissolve it in its own weight of boiling H2O and cool it for several days below 0o; the tetrahydrate crystallises from solution much more slowly when free from HNO3. It is less soluble in bicarbonate solutions than in H2O. Drying the solid over H2SO4 yields the monohydrate. The anhydrous crystals can be obtained by recrystallisation from dry Me2CO or AcOH followed by washing with dry Et2O, or by sublimation in a vacuum. On heating it turns pink at 230o and decomposes at ca 256o. It is acidic to litmus. [Hartman & Sheppard Org Synth Coll Vol III 37 1955.] It forms a compound with urea which crystallises from H2O in yellow needles that become red at 170o and decompose at 185-186o. [Beilstein 24 H 500, 24 I 428, 24 II 301, 24 III/IV 2137.]

ALLOXAN MONOHYDRATE Preparation Products And Raw materials

Raw materials

ALLOXAN MONOHYDRATESupplier

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