| Identification | More | [Name]
5-IODOURIDINE | [CAS]
1024-99-3 | [Synonyms]
2,4-DIHYDROXY-5-IODO-1-BETA-D-RIBOFURANOSYLPYRIMIDINE
5-IODO-1-(BETA-D-RIBOFURANOSYL)URACIL
5-IODOURIDINE
2,4-dihydroxy-5-iodo-1-β-d-ribofuranosylpyrimidine
5-Iodo-D-uridine
1-(β-D-Ribofuranosyl)-2-hydroxy-5-iodopyrimidine-4(1H)-one
1-β-D-Ribofuranosyl-2-hydroxy-5-iodo-1,4-dihydropyrimidine-4-one | [EINECS(EC#)]
213-833-1 | [Molecular Formula]
C9H11IN2O6 | [MDL Number]
MFCD00006532 | [Molecular Weight]
370.1 | [MOL File]
1024-99-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
205-207 °C (dec.) (lit.) | [density ]
2.27±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
Acetonitrile: Slightly soluble
Methanol: Soluble
Water: Slightly soluble | [form ]
Powder | [pka]
7.94±0.10(Predicted) | [color ]
White | [Water Solubility ]
Soluble in water. | [BRN ]
33665 | [InChI]
InChI=1S/C9H11IN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1 | [InChIKey]
RKSLVDIXBGWPIS-UAKXSSHOSA-N | [SMILES]
OC[C@H]1O[C@@H](N2C=C(I)C(=O)NC2=O)[C@H](O)[C@@H]1O | [CAS DataBase Reference]
1024-99-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S27:Take off immediately all contaminated clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [F ]
8-10 | [HS Code ]
29349990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
White powder | [Uses]
5-Iodouridine has shown to enhance the effect of gamma irradiation in hamster cells. It is used as catalytic agent, petrochemical additive, used in organic synthesis. | [Synthesis]
The general procedure for the synthesis of 5-iodouridine from 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione was carried out as follows: in a round-bottomed flask, uracil (1 g, 4.1 mmol) and iodine (1.15 g, 4.5 mmol) were dissolved in a mixture of chloroform (55 ml) and 1M Nitric acid (10 ml) in a mixed solution. The reaction mixture was heated to 80°C and refluxed for 5 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and the unfolding agent was a chloroform solution of 30% methanol (Rf: 0.60; raw material Rf: 0.45). After completion of the reaction, the mixture was cooled to 4 °C and colorless needle-like 5-iodouridine crystals were precipitated. The precipitate was collected by filtration and dried under vacuum overnight to give 1.39 g of 5-iodouridine in 92% yield. The product was subjected to nuclear magnetic resonance hydrogen (1H NMR, DMSO-d6, 300 MHz) and carbon (13C NMR, DMSO-d6, 300 MHz) spectra to confirm the structure, and mass spectrometry (ESI) showed that the molecular ion peak [M+NH4]+ was 388.0000, which was consistent with the theoretical value. | [Purification Methods]
Recrystallise 5iodouridine from H2O and dry it in vacuo at 100o. UV has max 289nm (0.01N HCl) and 278nm (0.01N NaOH). [Prusoff et al. Cancer Res 13 221 1953, Beilstein 24 III/IV 1235.] | [References]
[1] Bulletin of the Korean Chemical Society, 2018, vol. 39, # 9, p. 1054 - 1057
[2] Synthetic Communications, 1990, vol. 20, # 21, p. 3391 - 3394
[3] Canadian Journal of Chemistry, 1994, vol. 72, # 9, p. 2005 - 2010
[4] Patent: WO2011/51733, 2011, A2. Location in patent: Page/Page column 44
[5] Synthesis, 2009, # 23, p. 3957 - 3962 |
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