| Identification | More | [Name]
6-Azauracil | [CAS]
461-89-2 | [Synonyms]
1,2,4-TRIAZINE-3,5(2H,4H)-DIONE
1,2,4-TRIAZINE-3,5-DIONE
2H,4H-AS-TRIAZINE-3,5-DIONE
3,5-DIHYDROXY-1,2,4-TRIAZINE
6-AZA-2,4-DIHYDROXYPYRIMIDINE
6-AZAURACIL
AZAURACIL, 6-
TIMTEC-BB SBB004317
4(6)-Azauracil
As-Triazine-3,5(2H,4H)-dione
As-Triazine-3,5-diol
Azauracil
AZU
IPO 3834
ipo3834
NSC 3425
nsc3425
s-Triazine-3,5(2H,4H)-dione
USAF cb-30
1,2,4-triazine-3,5-diol | [EINECS(EC#)]
207-318-0 | [Molecular Formula]
C3H3N3O2 | [MDL Number]
MFCD00006456 | [Molecular Weight]
113.07 | [MOL File]
461-89-2.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow fine crystalline powder | [Melting point ]
274-275 °C(lit.)
| [Boiling point ]
211.75°C (rough estimate) | [density ]
1.5988 (rough estimate) | [refractive index ]
1.4264 (estimate) | [storage temp. ]
Store below +30°C. | [solubility ]
1 M NH4OH: 50mg/mL, clear to slightly hazy, colorless to light yellow-green | [form ]
Fine Crystalline Powder | [pka]
7.78±0.20(Predicted) | [color ]
White to light yellow | [Water Solubility ]
Partly soluble in water, ethanol, DMSO, and 1 M NH4OH (50 mg/ml). | [Detection Methods]
HPLC,NMR | [BRN ]
116472 | [InChI]
InChI=1S/C3H3N3O2/c7-2-1-4-6-3(8)5-2/h1H,(H2,5,6,7,8) | [InChIKey]
SSPYSWLZOPCOLO-UHFFFAOYSA-N | [SMILES]
N1=CC(=O)NC(=O)N1 | [CAS DataBase Reference]
461-89-2(CAS DataBase Reference) | [NIST Chemistry Reference]
1,2,4-Triazine-3,5(2H,4H)-dione(461-89-2) | [EPA Substance Registry System]
461-89-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,T | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R63:Possible risk of harm to the unborn child.
R25:Toxic if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S38:In case of insufficient ventilation, wear suitable respiratory equipment .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [RTECS ]
XY7700000
| [F ]
10-23 | [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29336980 | [Safety Profile]
Poison by
intraperitoneal route. Experimental
reproductive effects. Questionable
carcinogen with experimental tumorigenic
data. Mutation data reported. When heated
to decomposition it emits toxic fumes of
NOx. |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow fine crystalline powder | [Uses]
6-Azauracil (6-AU) is used as a growth inhibitor of various microorganisms via depletion of intracellular GTP and UTP nucleotide pools. 6-Azauracil has been widely used in investigations on modulation of transcription, especially in yeast models. | [Definition]
ChEBI: A 1,2,4-triazine compound having oxo-substituents at the 3- and 5-positions. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 23, p. 1522, 1958 DOI: 10.1021/jo01104a033 | [Biochem/physiol Actions]
6-Azauracil (6-AU) is a pyrimidine analog of uracil and exhibits antitumor activity. It inhibits the growth of various microorganisms by depleting intracellular guanosine triphosphate (GTP)?and uridine?triphosphate (UTP) nucleotide pools. | [Synthesis]
The general procedure for the synthesis of 1,2,4-triazine-3,5(2H,4H)-dione from the compound (CAS: 928-73-4) was as follows: 2-[2-(aminocarbonyl)fluorenylidene] 33.9 g (0.259 mol) and 51 g (1.275 mol) of sodium hydroxide were accurately weighed and dissolved in 150 mL of ethylene glycol. The reaction mixture was stirred continuously for 12 hours at 80 °C using a magnetic stirrer. Upon completion of the reaction, the mixture was cooled to room temperature, 250 mL of methanol was added and allowed to stand for 12 hours to promote crystallization. Subsequent filtration was carried out to recover the solvent to give 41.9 g of wet product. The wet product was dissolved in 60 mL of ultrapure water and the pH of the solution was adjusted with concentrated hydrochloric acid to less than 3. The solution was heated to 80 °C and stirring was maintained for half an hour before it was rapidly cooled to 10 °C with ice brine. The precipitate was collected by filtration and washed well with ultrapure water. Finally, the product was dried under vacuum to give 18 g (0.159 mol, 61.6% yield) of 6-azauracil (CD-2). | [Mode of action]
6-Azauracil is a growth inhibitor effective on a variety of microorganisms. It functions by depleting the intracellular GTP and UTP nucleotide supply. Mutations in transcriptional elongation machinery, as well as mutations in a variety of other pathways, exaggerate the growth defect of cells in the presence of 6 AU. | [References]
[1] Patent: CN108440505, 2018, A. Location in patent: Paragraph 0089; 0102; 0103; 0104
[2] Journal of Organic Chemistry, 1958, vol. 23, p. 1522
[3] Chemische Berichte, 1947, vol. 80, p. 494,500
[4] Patent: US2003/69140, 2003, A1
[5] Journal of the Iranian Chemical Society, 2016, vol. 13, # 8, p. 1539 - 1547 |
|
|