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| | Uridine 5'-monophosphate Basic information |
| Product Name: | Uridine 5'-monophosphate | | Synonyms: | U 5'-P;5’-ump;ump(nucleicacid);uridine5’-(dihydrogenphosphate);uridine5’-phosphoricacid;Uridylic acid, 5'-Uridylic acid, Uridine phosphate, 5'-UMP, Uridine 5'-phosphoric acid;uridinephosphate;uridine 5-monophosphate free acid | | CAS: | 58-97-9 | | MF: | C9H13N2O9P | | MW: | 324.18 | | EINECS: | 200-408-0 | | Product Categories: | 58-97-9 | | Mol File: | 58-97-9.mol |  |
| | Uridine 5'-monophosphate Chemical Properties |
| Melting point | 202°C (rough estimate) | | density | 1.865±0.06 g/cm3(Predicted) | | storage temp. | -20°C | | solubility | H2O: soluble50mg/mL, clear, colorless | | form | solid | | pka | pK1:6.63 (25°C) | | color | White to Off-White | | biological source | natural (organic) | | Water Solubility | H2O: soluble 50mg/mL, clear, colorless | | InChI | InChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1 | | InChIKey | DJJCXFVJDGTHFX-XVFCMESISA-N | | SMILES | P(OC[C@H]1O[C@@H](N2C=CC(=O)NC2=O)[C@H](O)[C@@H]1O)(O)(O)=O | | CAS DataBase Reference | 58-97-9 | | EPA Substance Registry System | 5'-Uridylic acid (58-97-9) |
| Safety Statements | 24/25 | | WGK Germany | 3 | | RTECS | YU8088000 | | TSCA | TSCA listed | | HS Code | 29349990 | | Storage Class | 11 - Combustible Solids |
| | Uridine 5'-monophosphate Usage And Synthesis |
| Description | Uridine 5'-monophosphateis a nucleotide that is synthesized from uridine. Uridine 5'-monophosphate has been shown to have anticancer activity in vitro and in vivo, as well as antiviral activity against herpes viruses. It is also used in foods such as infant formula to as a method of increasing uridine levels in blood. | | Chemical Properties | (Uridine-3′-phosphate) Crystallizes in
prisms from methanol. Freely soluble in water and alcohol; dextrorotatory
in solution. | | Uses | Uridine 5'-monophosphate is a nucleotide used as monomer in RNA. It is used in foods such as infant formula to as a method of increasing uridine levels in blood. | | Uses | Biochemical research. | | Definition | The monophosphoric ester of uracil, i.e., the nucleotide containing uracil-d-ribose and phosphoric acid. The phosphate may be esterified to either the 2, 3, or 5 carbon of ribose, yielding uridine-2′-phosphate, uridine-3′phosphate, and uridine-5′-phosphate, respectively. | | Application | Uridine 5'-monophosphate (5'-Uridylic acid) is an orally active mitochondrial ATP-dependent potassium channel
activator that has a protective effect on the heart. Uridine
5'-monophosphate can promote the synthesis of CDP-choline and induce apoptosis in intestinal epithelial cells, which is beneficial for gut development and reduces diarrhea. | | General Description | Uridine 5'-monophosphate acts as a precursor for all pyrimidine nucleotides. | | Synthesis | The general procedure for the synthesis of ((2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyldihydrophosphoric acid and the compound (CAS: 3803-29-0) from the compound (CAS: 56428-57-0) was carried out as follows: selected activated nucleotides of a 15 mM solution and ImpN (N = A, U, C, G, dA) were dissolved in 1 M sodium fluoride (Sigma). The reaction mixtures were allowed to stand at 24°C for 8-10 days, during which time the progress of the reaction was monitored periodically by HPLC using a reversed-phase column. Upon completion of the reaction, each product mixture contained predominantly the corresponding fluorinated phosphate ester and a small amount of NMP hydrolysis product. Separation was carried out using a semipreparative reversed-phase Alltima C-18, 5 μm (10 mm × 300 mm) column (Alltech, Grace Davison) under isocratic elution conditions (88% aqueous 0.2% formic acid (Sigma) with 12% 30% acetonitrile). The flow rate was set at mL/min. the collected fractions were characterized by mass spectrometry. | | References | [1] Tetrahedron Letters, 2014, vol. 55, # 8, p. 1464 - 1466 |
| | Uridine 5'-monophosphate Preparation Products And Raw materials |
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