| Identification | More | [Name]
ALLOXAN MONOHYDRATE | [CAS]
2244-11-3 | [Synonyms]
2,4,5,6(1H,3H)-PYRIMIDINETETRONE MONOHYDRATE
2,4,5,6-TETRAOXYPYRIMIDINE
2,4,5,6-TETRAOXYPYRIMIDINE MONOHYDRATE
5,6-DIOXYURACIL
5,6-DIOXYURACIL MONOHYDRATE
ALLOXANE DIHYDRATE
ALLOXAN MONOHYDRATE
LABOTEST-BB LT00138148
MESOXALYLUREA
MESOXALYLUREA, MONOHYDRATE
2,4,5,6(1h,3h)-pyrimidinetetronehydrate
2,4,5,6-tetraoxohexahydropyrimidinehydrate
mesoxalylcarbamidemonohydrate
Alloxan99%
ALLOXAN ( HYDRATE) GR
2,4,5,6(1H,3H)-Pyrimidinetetrone, 2,4,5,6-Tetraoxypyrimidine, 5,6-Dioxyuracil
Pyrimidine-2,4,5,6(1H,3H)-tetrone hydrate | [EINECS(EC#)]
251-501-8 | [Molecular Formula]
C4H4N2O5 | [MDL Number]
MFCD00149399 | [Molecular Weight]
160.08 | [MOL File]
2244-11-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white to beige-yellowish crystalline powder | [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]
2244-11-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3
| [RTECS ]
UW0492000
| [TSCA ]
Yes | [HS Code ]
29335990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral | [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. |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white to beige-yellowish crystalline powder | [Uses]
A cytotoxic compound, Alloxan Monohydrate causes oxidative base damage to nuclear DNA.
| [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]
specific cytotoxin (beta pacreatic cell) | [Synthesis]
The original tetracosane was prepared by oxidizing uric acid with nitric acid, or by oxidizing barbituric acid with chromium trioxide. | [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.] |
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