| Identification | More | [Name]
Spongouridine | [CAS]
3083-77-0 | [Synonyms]
1-BETA-D-ARABINOFURANOSYLURACIL
2'-ARAURIDINE
ARABINOFURANOSYLURACIL
ARABINOSYL-URACIL
ARA-U
URACIL-1-BETA-D-ARABINOFURANOSIDE
URACIL BETA-D-ARABINOFURANOSIDE
1-beta-d-arabinofuranosyl-uraci
3h)-pyrimidinedione,1-beta-d-arabinofuranosyl-4(1h
arauridine
spongouridin
uracilarabinoside
1-β-D-Arabinofuranosyluracil
Uracil 1-β-D-arabinofuranoside
1-beta-D-arabinofuranosyl-(1H,3H)-pyrimidine-2,4-dione
URACIL B-D-ARABINOFURANOSIDE
Arabinfuranosyluracil
Uracil arabinofuranoside
1-b-D-Arabinofuranosyluracil
1-SS-D-ARABINOFURANOSYLURACIL | [EINECS(EC#)]
221-386-9 | [Molecular Formula]
C9H12N2O6 | [MDL Number]
MFCD00065998 | [Molecular Weight]
244.2 | [MOL File]
3083-77-0.mol |
| Chemical Properties | Back Directory | [Appearance]
White to Off-White Solid | [Melting point ]
220-222°C | [storage temp. ]
2-8°C
| [solubility ]
Methanol (Slightly), Water (Slightly) | [density ]
1.674±0.06 g/cm3(Predicted) | [form ]
Powder | [pka]
pK1:9.30 (25°C) | [color ]
White to Off-white | [biological source]
synthetic (organic) | [Water Solubility ]
water: 50mg/mL, clear, colorless | [Usage]
Antiviral agent. Used for the treatment of severe acute respiratory syndrome (SARS). | [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) |
| Raw materials And Preparation Products | Back Directory | [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 |
| Hazard Information | Back Directory | [Description]
1-β-D-Arabinofuranosyluracil (ara-U) is an inactive metabolite of cytarabine (Item No. 16069).1 Ara-U is formed when cytarabine undergoes deamination by cytidine deaminase. | [Chemical Properties]
White to Off-White Solid | [Uses]
Antiviral agent.1-β-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 |
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| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
|