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U1752

Sigma-Aldrich

Uridine 5′-monophosphate

≥98%

Synonym(s):

U 5′-P, UMP, Uridylic acid

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About This Item

Empirical Formula (Hill Notation):
C9H13N2O9P
CAS Number:
58-97-9
Molecular Weight:
324.18
EC Number:
200-408-0
MDL number:
MFCD00067346
UNSPSC Code:
41106305
PubChem Substance ID:
24900628
NACRES:
NA.51

biological source

natural (organic)

Quality Level

200

Assay

≥98%

form

powder

solubility

H2O: soluble 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

OC1C(O)C(OC1COP(O)(O)=O)N2C=CC(=O)NC2=O

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)

InChI key

DJJCXFVJDGTHFX-UHFFFAOYSA-N

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General description

Uridine 5′-monophosphate acts as a precursor for all pyrimidine nucleotides.

Application

Uridine 5′-monophosphate has been used as a component in isotonic E3 medium for isotonic reconstitution experiments to study its effects on the basal cell response or epithelial cell migration to the wound in the isotonic medium.

Biochem/physiol Actions

Uridine 5′-monophosphate (UMP) is a nucleotide monomer in RNA. It contains the nucleobase uracil along with the ribose sugar and a phosphate group. UMP dietary supplementation enhances neurotransmitter release and neurite outgrowth and also promotes membrane phosphatide production in adult rats. Oral supplementation of DHA, co-administered with UMP, in adult gerbils shows an increase in dendritic spines and neuronal membrane synthesis. It suggests a strategy for the treatment of cognitive disorders resulting from synapse loss.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Regulation of uridylic acid biosynthesis in the cyanobacterium Anabaena variabilis.
Currier TC and Wolk CP
Journal of Bacteriology, 136(2), 682-687 (1978)
Lei Wang et al.
Journal of molecular neuroscience : MN, 27(1), 137-145 (2005-08-02)
Membrane phospholipids like phosphatidylcholine (PC) are required for cellular growth and repair, and specifically for synaptic function. PC synthesis is controlled by cellular levels of its precursor, cytidine-5'-diphosphate choline (CDP-choline), which is produced from cytidine triphosphate (CTP) and phosphocholine. In
Toshimasa Sakamoto et al.
Brain research, 1182, 50-59 (2007-10-24)
Docosahexaenoic acid (DHA), an omega-3 polyunsaturated fatty acid, is an essential component of membrane phosphatides and has been implicated in cognitive functions. Low levels of circulating or brain DHA are associated with various neurocognitive disorders including Alzheimer's disease (AD), while
Xiaozhen Chen et al.
Journal of pharmaceutical and biomedical analysis, 174, 432-440 (2019-06-21)
A novel, simple, and efficacious analytical method for determining of nucleotides in Anoectochilus roxburghii (Wall.) Lindl (A. roxburghii) was developed. Magnetic dispersive solid-phase micro-extraction (MDSPME) combined with high-performance liquid chromatography was applied for extraction and determination of three nucleotides, such
Masahiro Fujihashi et al.
The Journal of biological chemistry, 288(13), 9011-9016 (2013-02-12)
Orotidine 5'-monophosphate decarboxylase (ODCase) accelerates the decarboxylation of its substrate by 17 orders of magnitude. One argument brought forward against steric/electrostatic repulsion causing substrate distortion at the carboxylate substituent as part of the catalysis has been the weak binding affinity
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Protocols

LC/MS Analysis of Nucleotides SeQuant® ZIC®-cHILIC – Effect of pH

ZIC®-cHILIC is a densely bonded zwitterionic stationary phase with phosphorylcholine functional groups covalently attached to silica.

LC/MS Analysis of Nucleotides on SeQuant ZIC-cHILIC

HILIC separation is an alternative that permits sensitive MS detection and without the use of ion-pair reagents.

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