4004-57-3

Basic information

• Product Name: Uridine 3',5'-cyclic monophosphate
• Synonyms: cyclic 3',5'-uridine monophosphate;3',5'-cyclic UMP
• CAS NO: 4004-57-3
• Molecular Formula: C₉H₁₁N₂O₈P
• Molecular Weight: 306.166
• Mol File: 4004-57-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.85g/cm³
• Refractive Index: 1.65
• CAS DataBase Reference: Uridine 3',5'-cyclic monophosphate(CAS DataBase Reference)
• NIST Chemistry Reference: Uridine 3',5'-cyclic monophosphate(4004-57-3)
• EPA Substance Registry System: Uridine 3',5'-cyclic monophosphate(4004-57-3)

Safety Data

• Hazardous Substances Data: 4004-57-3(Hazardous Substances Data)

Usage

Definition

ChEBI: A 3',5'-cyclic pyrimidine nucleotide having uridine as the nucleobase.

InChI:InChI=1/C9H11N2O8P/c12-5-1-2-11(9(14)10-5)8-6(13)7-4(18-8)3-17-20(15,16)19-7/h1-2,4,6-8,13H,3H2,(H,15,16)(H,10,12,14)/t4-,6-,7-,8-/m1/s1

Upstream product

• 110-86-1 pyridine 
• 58-97-9 5'-Uridylic Acid 
• 538-75-0 dicyclohexyl-carbodiimide 
• 63-39-8 UTP 

Downstream Products

• 58-97-9 5'-Uridylic Acid 
• 66-22-8 uracil 
• 84-53-7 uridine-3'-phosphate 
• 131-83-9 uridine 2'-monophosphate 

Relevant articles and documents

Membrane-permeable octanoyloxybenzyl-masked cNMPs as novel tools for non-invasive cell assays

Adenine nucleotide (AN) 2nd messengers, such as 3',5'-cyclic adenosine monophosphate (cAMP), are central elements of intracellular signaling, but many details of their underlying processes remain elusive. Like all nucleotides, cyclic nucleotide monophosphates (cNMPs) are net-negatively charged at physiologic pH which limits their applicability in cell-based settings. Thus, many cellular assays rely on sophisticated techniques like microinjection or electroporation. This setup is not feasible for medium- to high-throughput formats, and the mechanic stress that cells are exposed to raises the probability of interfering artefacts or false-positives. Here, we present a short and flexible chemical route yielding membrane-permeable, bio-reversibly masked cNMPs for which we employed the octanoyloxybenzyl (OB) group. We further show hydrolysis studies on chemical stability and enzymatic activation, and present results of real-time assays, where we used cAMP and Ca2+ live cell imaging to demonstrate high permeability and prompt intracellular conversion of some selected masked cNMPs. Based on these results, our novel OB-masked cNMPs constitute valuable precursor-tools for non-invasive studies on intracellular signaling.

Studies on pyrophosphates. Part III. A new method for the synthesis of nucleotide coenzymes by means of di-n-butylphosphiothioyl bromide.

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