Physicochemical Properties
| Molecular Formula | C₉H₁₂N₂O₅ |
| Molecular Weight | 228.20 |
| Exact Mass | 228.074 |
| Elemental Analysis | C, 47.37; H, 5.30; N, 12.28; O, 35.05 |
| CAS # | 951-78-0 |
| Related CAS # | 2'-Deoxyuridine-1′-13C;478510-85-9;2'-Deoxyuridine-2′-13C;478510-87-1;2'-Deoxyuridine-3′-13C;478510-89-3;2'-Deoxyuridine-5′-13C;478510-91-7;2'-Deoxyuridine-d2;478511-30-7;2'-Deoxyuridine-d;2'-Deoxyuridine-13C,15N2;369656-76-8;2'-Deoxyuridine-d2-1;40632-23-3 |
| PubChem CID | 13712 |
| Appearance | Typically exists as white to off-white solids at room temperature |
| Density | 1.5±0.1 g/cm3 |
| Melting Point | 167-169 °C(lit.) |
| Index of Refraction | 1.603 |
| LogP | -1.7 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 16 |
| Complexity | 343 |
| Defined Atom Stereocenter Count | 3 |
| SMILES | O=C1NC(=O)C=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 |
| InChi Key | MXHRCPNRJAMMIM-SHYZEUOFSA-N |
| InChi Code | InChI=1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1 |
| Chemical Name | 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione |
| Synonyms | 2'-DeoxyuridineUridine, Uracil deoxyriboside2'-deoxy deoxyuridine; 2'-DEOXYURIDINE; 951-78-0; deoxyuridine; Uracil deoxyriboside; 2-Deoxyuridine; 1-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione; Uridine, 2'-deoxy-; Deoxyribose uracil; |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Endogenous Metabolite |
| ln Vitro | Deoxyuridine (dU) increases chromosome breakage at folic acid (FA)-sensitive common fragile sites (mostly 3p14 and 16q23) in human lymphocytes. This dU-related increase can be suppressed by thymidine or FA. These results suggest that the mechanism of fragile site expression in low FA medium involves misincorporation of dU into DNA[1]. |
| Enzyme Assay | A new photoisomeric nucleoside dUAz bearing an azobenzene group at the C5-position of 2'-deoxyuridine was designed and synthesized. Photoisomerization of dUAz in oligodeoxynucleotides can be achieved rapidly and selectively with 365 nm (forward) and 450 nm (backward) irradiation. Thermal denaturation experiments revealed that dUAz stabilized the duplex in the cis-form and destabilized it in the trans-form with mismatch discrimination ability comparable to thymidine. These results indicate that dUAz could be a powerful material for reversibly manipulating nucleic acid hybridization with spatiotemporal control[2]. |
| References |
[1]. Deoxyuridine increases folate-sensitive fragile site expression in human lymphocytes. Am J Med Genet. 1987 Jan;26(1):1-5. [2]. Development of ZIC-HILIC methods using ultraviolet detection for determining 2-deoxyuridine in human serum. Systematic Reviews in Pharmacy. 2020 March; 11(2):388-394. [3]. Thymidine and 2'-deoxyuridine reduce microglial activation and improve oxidative stress damage by modulating glycolytic metabolism on the Aβ25-35-induced brain injury. Arch Biochem Biophys. 2022 Oct 30;729:109377. |
| Additional Infomation |
2'-deoxyuridine is a pyrimidine 2'-deoxyribonucleoside having uracil as the nucleobase. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is functionally related to a uracil. Deoxyuridine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). 2'-Deoxyuridine has been reported in Homo sapiens, Biemna ehrenbergi, and other organisms with data available. Deoxyuridine is a nucleoside consisting of uracil and deoxyribose, which can act as an intermediate in thymidine synthesis. Deoxyuridine (dU) is used to indirectly determine if there are sufficient levels of folate and cobalamin in cell or tissue samples. 2'-Deoxyuridine. An antimetabolite that is converted to deoxyuridine triphosphate during DNA synthesis. Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemias due to vitamin B12 and folate deficiencies. |
Solubility Data
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~438.21 mM) H2O : ~100 mg/mL (~438.21 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (9.11 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (9.11 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (9.11 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 100 mg/mL (438.21 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.3821 mL | 21.9106 mL | 43.8212 mL | |
| 5 mM | 0.8764 mL | 4.3821 mL | 8.7642 mL | |
| 10 mM | 0.4382 mL | 2.1911 mL | 4.3821 mL |