26287-69-4

Basic information

• Product Name: L-Uridine
• Synonyms: BETA-L-URIDINE;L-URIDINE (1-(β-L-RIBOFURANOSYL)URACIL);1-beta-L-Ribofuranosyl-2,4(1H,3H)-pyrimidinedione;L-Uridine;1-((2S,3S,4R,5S)-3,4-Dihydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione
• CAS NO: 26287-69-4
• Molecular Formula: C₉H₁₂N₂O₆
• Molecular Weight: 244.2
• EINECS: 500-100-4
• Mol File: 26287-69-4.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Density: 1.674
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 9.39±0.10(Predicted)
• CAS DataBase Reference: L-Uridine(CAS DataBase Reference)
• NIST Chemistry Reference: L-Uridine(26287-69-4)
• EPA Substance Registry System: L-Uridine(26287-69-4)

Safety Data

• Hazardous Substances Data: 26287-69-4(Hazardous Substances Data)

Usage

General Description

L-Uridine is a nucleoside that is composed of the pyrimidine base uracil and the sugar ribose. It plays a crucial role in various physiological functions, particularly in the synthesis of RNA and the production of neurotransmitters such as dopamine and serotonin. L-Uridine is also involved in the regulation of cell signaling and the modulation of synaptic plasticity, which impacts learning and memory. Additionally, it has been studied for its potential positive effects on mood, cognitive function, and neuroprotection. L-Uridine is available as a nutritional supplement and is being researched for its potential therapeutic applications in neurodegenerative diseases and mood disorders.

Upstream product

• 31501-46-9 (2S,3S,3aR,9aS)-3-hydroxy-2-(hydroxymethyl)-2,3,3a,9a-tetrahydro-6H-furo[2,3’:4,5]oxazolo[3,2-a]pyrimidin-6-one 
• 1092978-60-3 Toluene-4-sulfonic acid (3R,4R,5R)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester 
• 58-96-8 uridine 
• 31615-96-0 3',5'-di-O-benzoyl-2,2'-anhydro-L-uridine 
• 35939-60-7 2-amino-β-L-arabinofurano[1',2':4,5]oxazoline 
• 31615-98-2 1-(3,5-Di-O-benzoyl-β-L-arabinofuranosyl)uracil 

Downstream Products

• 1382804-40-1 C₃₀H₂₃BrN₂O₉ 
• 1382804-38-7 C₃₀H₂₃ClN₂O₉ 
• 1382804-62-7 C₃₄H₂₆IN₃O₈S 
• 1382804-60-5 C₃₄H₂₆BrN₃O₈S 
• 1382804-58-1 C₃₄H₂₆ClN₃O₈S 
• 1382804-56-9 C₃₄H₂₇N₃O₈S 
• 1382804-54-7 C₃₀H₂₄IN₃O₈ 
• 1382804-53-6 C₃₀H₂₄BrN₃O₈ 
• 1382804-51-4 C₃₀H₂₄ClN₃O₈ 
• 1382804-49-0 2',3',5'-tri-O-benzoyl-ara-L-cytidine 
• 1382804-47-8 C₃₄H₂₅IN₂O₉S 
• 1382804-45-6 C₃₄H₂₅BrN₂O₉S 
• 1382804-43-4 C₃₄H₂₅ClN₂O₉S 
• 1748-04-5 2',3',5'-tri-O-benzoyl-ara-L-uridine 

Relevant articles and documents

Enantioselective synthesis and biological evaluation of 5-o-carboranyl pyrimidine nucleosides

Base-modified carborane-containing nucleosides such as 5-o-carboranyl-2'-deoxyuridine (CDU) when combined with neutrons have potential for the treatment of certain malignancies. Lack of toxicity in various cells, high accumulation in cancer cells and intracellular phosphorylation are desirable characteristics for modified nucleosides used in boron neutron capture therapy (BNCT) for brain tumors and other malignancies. The aim of this work was to synthesize the two β-enantiomers of several 5-o-carboranyl-containing nucleosides. These derivatives may possess favorable properties such as high lipophilicity, high transportability, the ability to be phosphorylated, and resistance to catabolism. β-Isomers of 2',3'-dihydroxynucleosides and analogues containing a heteroatom in the sugar moiety were also synthesized. Carboranyl pyrimidine nucleosides were prepared either from the parent β-D-nucleoside, β-L-nucleoside, or by a coupling reaction. The dioxolane derivative 7Scheme 1Reagents and conditions: (a) 1,1,1,3,3,3-hexamethydisilazane, ammonium sulfate, reflux, 6 h; (b) tin(IV) chloride, CH2Cl2, 0°C, 2h; (c) tetrabutylammonium fluoride, 1 M sol in THF, 0°C, 3h. was prepared by a coupling reaction between protected 5-o-carboranyluracil (8, CU) and the corresponding protected heterocycle. Specific catalysts were used during the N-glycosylation process to favor the formation of the β-isomer. Biological evaluation of these new chiral 5-o-carboranyl pyrimidine derivatives indicated that most of these compounds have low toxicity in a variety of normal and malignant cells and achieved high cellular levels in a lymphoblastoid cell line. Increasing the number of hydroxyl groups on the sugar moiety decreased the cellular accumulation and serum binding to different extents. Five compounds were identified for further biological evaluation as potential agents for BNCT. Copyright (C) 1999 Elsevier Science Ltd.

Synthesis of 1-β-L-arabinofuranosylcytosine (β-L-Ara-C) and 2'-deoxy- 2'-methylene-β-L-cytidine (β-L-DMDC) as potential antineoplastic agents

1-β-L-Arabinofuranosylcytosine (β-L-Ara-C, 7) and 2'-deoxy-2'-methylene- β-L-cytidine (β-L-DMDC, 14) have been synthesized via a multi-step synthesis from L-arabinose. These compounds were tested in vitro against L1210, P388, Sarcoma 180, and CEM cells, and found not to be active at a concentration up to 100 μM. β-L-Ara-C and β-L-DMDC were also tested against HSV-1 and HSV-2 and yielded ID50 values of >100 μM.

Hydrolysis of Tosyl Esters Initiated by an Electron Transfer from Photoexcited Electron-Rich Aromatic Compounds

Selective hydrolysis of tosyl esters was realized by irradiation of Uv light (>300 nm) in the presence of electron-rich aromatic compounds and the reaction proceeds via en electron-transfer process.