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 Information

Safety Statements 

24/25

WGK Germany 

3

RTECS 

YU8088000

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich

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.

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.                                                           

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.

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(58-97-9)Related Product Information

• Uridine 5′-monophosphate disodium salt
• 3'-Uridylic acid, disodium salt
• Uridine
• UTP
• URIDINE-13C9, 15N2-5 TRIPHOSPHATE SODI U
• DMT-2′O-TBDMS-rU Phosphoramidite
• UDP
• Guanosine-5'-diphosphate disodium salt
• UDPGA TRISODIUM SALT
• Uridine-5'-triphosphoric acid trisodium salt
• UDP-ALPHA-D-GALACTOSE DISODIUM SALT
• Uridine-5'-diphosphate disodium salt
• Uridine Diphosphate Choline
• Uridine Diphosphate Choline Ammonium Salt
• 2',3',5'-TRI-O-BENZOYLURIDINE
• Uridine-5-oxyacetic acid methyl ester
• Uridine Diphosphate-GlcNaz
• BPBNNONNJSGJLR-UHFFFAOYSA-L