Introduction：Basic information about 1-beta-D-Arabinofuranosyluracil CAS 3083-77-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
1-beta-D-Arabinofuranosyluracil Basic information
| Product Name: | 1-beta-D-Arabinofuranosyluracil |
| Synonyms: | 1--D-Arabinofuranosyl-2,4(1H,3H)-pyrimidinedione;NSC 68928;1-BETA-D-ARABINOFURANOSYLURACIL;1-(β-D-Arabinopyranosyl)uracil;uracilarabinoside;ARABINOSYL-URACIL;ARABINOFURANOSYLURACIL;ARA-U |
| CAS: | 3083-77-0 |
| MF: | C9H12N2O6 |
| MW: | 244.2 |
| EINECS: | 221-386-9 |
| Product Categories: | Bases & Related Reagents;Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;3083-77-0;Nucleosides-Arabinonuleosides |
| Mol File: | 3083-77-0.mol |
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1-beta-D-Arabinofuranosyluracil Chemical Properties
| Melting point | 220-222°C |
| storage temp. | -20°C |
| solubility | Methanol (Slightly), Water (Slightly) |
| pka | pK1:9.30 (25°C) |
| density | 1.674±0.06 g/cm3(Predicted) |
| form | Powder |
| color | White to Off-white |
| biological source | synthetic (organic) |
| Water Solubility | water: 50mg/mL, clear, colorless |
| BRN | 28749 |
| Major Application | pharmaceutical |
| InChI | InChI=1/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7+,8-/s3 |
| InChIKey | DRTQHJPVMGBUCF-YEZNIHIWNA-N |
| SMILES | O[C@H]1[C@@H]([C@@H](CO)O[C@H]1N1C=CC(=O)NC1=O)O |&1:1,2,3,7,r| |
| CAS DataBase Reference | 3083-77-0(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 22-24/25-36-26 |
| WGK Germany | 3 |
| RTECS | YQ8818000 |
| F | 3 |
| HS Code | 29349990 |
| Storage Class | 13 - Non Combustible Solids |
1-beta-D-Arabinofuranosyluracil Usage And Synthesis
| Description | 1-β-D-Arabinofuranosyluracil (ara-U) is an inactive metabolite of cytarabine . Ara-U is formed when cytarabine undergoes deamination by cytidine deaminase. |
| Chemical Properties | White to Off-White Solid |
| Uses | 1-beta-D-Arabinofuranosyluracil is used for the treatment of severe acute respiratory syndrome (SARS). |
| Definition | ChEBI: A natural product found in Lepisorus contortus. |
| Synthesis | A classic synthetic method for 1-beta-D-Arabinofuranosyluracil (arabinoside Ara-U) is a two-step process using uridine as a starting material: First, uridine is heated with diphenyl carbonate in dimethylformamide (DMF) with potassium carbonate or sodium bicarbonate as a catalyst, resulting in dehydration cyclization to generate the key intermediate 2,2'-anhydrouridine. Subsequently, under acidic conditions (e.g., using 2 N HCl), hydrolysis occurs, causing nucleophilic ring-opening of the dehydration bond and introducing a β-hydroxyl group at the C-2' position, ultimately yielding the target product Ara-U. |
| References | [1] DI LIANG . Simultaneous determination of 1-β-d-Arabinofuranosylcytosine and two metabolites, 1-β-d-Arabinofuranosyluracil and 1-β-d-Arabinofuranosylcytosine triphosphate in leukemic cell by HPLC-MS/MS and the application to cell pharmacokinetics[J]. Journal of Chromatography B, 2014, 962: Pages 14-19. DOI: 10.1016/j.jchromb.2014.05.003
[2] YOUCEF MEHELLOU . Phosphoramidates of 2′-β-d-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism[J]. Bioorganic & Medicinal Chemistry, 2010, 18 7: Pages 2439-2446. DOI:10.1016/j.bmc.2010.02.059. |
1-beta-D-Arabinofuranosyluracil Preparation Products And Raw materials
| Raw materials | 6H-Furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one, 2,3,3a,9a-tetrahydro-3-hydroxy-2-(hydroxymethyl)-, (2R,3R,3aR,9aR)--->2,2'-Cyclouridine-->Gemcitabine-->Cytarabine-->Uridine |
| Preparation Products | Vidarabine-->THYMINE-BETA-D-ARABINOFURANOSIDE-->Cytarabine Impurity 12 |
