ChemicalBook CAS DataBase List 58-97-9

58-97-9

Name	UMP
CAS	58-97-9
EINECS(EC#)	200-408-0
Molecular Formula	C9H13N2O9P
MDL Number	MFCD00067346
Molecular Weight	324.18
MOL File	58-97-9.mol

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 Data

Safety Statements	24/25 less more
WGK Germany	3
RTECS	YU8088000
TSCA	TSCA listed
HS Code	29349990

Raw materials And Preparation Products

Hazard Information

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

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

56428-57-0

58-97-9

Uridine, 5'-(hydrogen phosphorofluoridate)

3803-29-0

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.

storage

Store at -20°C

References

[1] Tetrahedron Letters, 2014, vol. 55, # 8, p. 1464 - 1466

Spectrum Detail

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