6757-06-8

Basic information

• Product Name: Cytidine 5'-monophosphate disodium salt
• Synonyms: 5'-CMP 2NA;5'-CYTIDYLIC ACID DISODIUM SALT;CYTIDYLIC ACID DISODIUM SALT;CYTIDINE-5'-MONOPHOSPHATE SODIUM SALT;CYTIDINE-5'-MONOPHOSPHATE DISODIUM SALT;CYTIDINE 5'-PHOSPHATE, SODIUM SALT;CYTIDINE-5'-MONOPHOSPHORIC ACID, DISODIUM;CMP, NA2
• CAS NO: 6757-06-8
• Molecular Formula: C₉H₁₂N₃O₈P*2Na
• Molecular Weight: 367.16
• EINECS: 229-819-3
• Product Categories: Amino Acids;Biochemistry;Nucleosides, Nucleotides & Related Reagents;Nucleotides and their analogs;Nucleic acids
• Mol File: 6757-06-8.mol

Chemical Properties

• Melting Point: 300 °C
• Boiling Point: 678.1oC at 760 mmHg
• Flash Point: 363.9oC
• Appearance: White/crystalline
• Density: 2.15g/cm3
• Refractive Index: 8 ° (C=2, H2O)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Cytidine 5'-monophosphate disodium salt(CAS DataBase Reference)
• NIST Chemistry Reference: Cytidine 5'-monophosphate disodium salt(6757-06-8)
• EPA Substance Registry System: Cytidine 5'-monophosphate disodium salt(6757-06-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-37/39-36-26
• WGK Germany: 3
• F: 1-10
• Hazardous Substances Data: 6757-06-8(Hazardous Substances Data)

Usage

Uses

1. Used in Nucleotide Stock Solutions:
Cytidine 5'-monophosphate disodium salt is used as an ectonucleotidase (ENTase) inhibitor for probing 5'-ENTase activity in cortical neurons. This application helps researchers understand the role of ENTase in neuronal function and its potential involvement in various neurological disorders.
2. Used in In Vitro Studies:
Cytidine 5'-monophosphate disodium salt is utilized in in vitro studies to estimate its effect on the growth response of selected bacteria strains that dominate the piglets' small intestine. This application aids in understanding the role of CMP disodium salt in bacterial growth and its potential implications for gut health and overall animal health.
3. Used in Pharmaceutical Industry:
Cytidine 5'-monophosphate disodium salt is used as a raw material for the synthesis of various nucleotides and nucleosides, which are essential for the development of new drugs targeting different diseases, including cancer and viral infections.
4. Used in Research and Development:
Cytidine 5'-monophosphate disodium salt is employed as a research tool in the field of molecular biology and genetics. It is used for studying the structure, function, and regulation of nucleic acids, as well as for the development of new diagnostic and therapeutic approaches.
5. Used in Food Industry:
Cytidine 5'-monophosphate disodium salt is used as a flavor enhancer in the food industry, particularly in the production of savory and umami flavors. It is often used in combination with other nucleotides, such as inosine 5'-monophosphate, to enhance the taste of various food products.

Biochem/physiol Actions

Cytidine monophosphate?(CMP) serve as a nucleotide?carrier for sugars.

Synthetic route

C9H14N4O10P2(2-)*2Na(1+) → cytidine-5'-monophosphate disodium salt (6757-06-8)

Conditions	Yield
With water; zinc(II) cation pH=5.5;

1,10-Phenanthroline (66-71-7) + copper(II) nitrate hexahydrate + cytidine-5'-monophosphate disodium salt (6757-06-8) + water (7732-18-5) → [Cu7(1,10-phenanthroline)6(cytidine 5'-monophosphate)4]*(NO3)6*(H2O)46

Conditions	Yield
In ethanol at 40℃;	76%

Cu(NO3)2*2(ethylenediamine) + cytidine-5'-monophosphate disodium salt (6757-06-8) + water (7732-18-5) → [Cu2(ethylenediamine)2(cytidine 5'-monophosphate)2]*5H2O

Conditions	Yield
In methanol for 0.5h; pH=4;	75%

cobalt(II) nitrate hexahydrate + cytidine-5'-monophosphate disodium salt (6757-06-8) + water (7732-18-5) + trans-1,2-bis(4-pyridyl)ethylene (1135-32-6) → [Co(HCMP)2(bis(4-pyridyl)ethylene)(H2O)2]·3.5H2O

Conditions	Yield
Stage #1: cobalt(II) nitrate hexahydrate; cytidine-5'-monophosphate disodium salt; water for 0.5h; Stage #2: trans-1,2-bis(4-pyridyl)ethylene With nitric acid In ethanol at 20℃; for 0.5h; pH=5;	72%

manganese(II) perchlorate hexahydrate + cytidine-5'-monophosphate disodium salt (6757-06-8) + water (7732-18-5) + trans-1,2-bis(4-pyridyl)ethylene (1135-32-6) → [Mn(bis(4-pyridyl)ethylene)(H2O)4]·(CMP)·3H2O

Conditions	Yield
Stage #1: manganese(II) perchlorate hexahydrate; cytidine-5'-monophosphate disodium salt; water for 0.5h; Stage #2: trans-1,2-bis(4-pyridyl)ethylene With sodium hydroxide In ethanol at 20℃; for 0.5h; pH=6;	68%

manganese(II) perchlorate hexahydrate + cytidine-5'-monophosphate disodium salt (6757-06-8) + water (7732-18-5) + trans-1,2-bis(4-pyridyl)ethylene (1135-32-6) → [Mn(bis(4-pyridyl)ethylene)3(H2O)2]·(ClO4)2·(bis(4-pyridyl)ethylene)2·5H2O

Conditions	Yield
Stage #1: manganese(II) perchlorate hexahydrate; cytidine-5'-monophosphate disodium salt; water for 0.5h; Stage #2: trans-1,2-bis(4-pyridyl)ethylene With sodium hydroxide In ethanol at 20℃; for 0.5h; pH=7;	68%

cytidine-5'-monophosphate disodium salt (6757-06-8)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In methanol at 0 - 20℃; for 24.25h;	42%

chromium(III)(L-ser)2(H2O)2Cl*H2O + cytidine-5'-monophosphate disodium salt (6757-06-8) → (chromium(III))2(L-ser)2(5'-CMP)(OH)Cl*7H2O

Conditions	Yield
In water soln. of nucleotide (pH=7) is added dropwise to a soln. of amino acid chromium complex, soln. is placed in a thermostated bath at 50°C with const. stirring for 8 h; soln. is concd. to 5 ml, chromy. (Sephadex), addn. of ethanol to the first (blue) fraction, further evapn., ppt. is vac. dried (P4O10); elem. anal.;

chromium(III)(L-met)(L-metH)Cl2*3H2O + cytidine-5'-monophosphate disodium salt (6757-06-8) → (chromium(III))2(L-met)(5'-CMP)2(OH)*10H2O

Conditions	Yield
In water soln. of nucleotide (pH approx. 7) is added dropwise to a soln. of amino acid chromium complex (pH 3.9-4.2), mixt. is maintained at 50°C with const. stirring for 1.5-2.5 h; ppt. is filtered off, washed with cold water and vac. dried (P4O10); elem. anal.;

trans-{CrCl2(C2H4(NH2)2)2}Cl (14240-29-0, 14301-97-4, 59109-96-5, 66653-37-0) + cytidine-5'-monophosphate disodium salt (6757-06-8) → Cr(3+)*NH2CH2CH2NH2*CONC(NH2)CHCHN(CHCHOHCHOHCH(CH2OPO3)O)(2-)*CONC(NH2)CHCHN(CHCHOHCHOHCH(CH2OPO3H)O)(1-)*8H2O

Conditions	Yield
In water aq. soln. of Cr compd. mixed with aq. soln. of org. compd. (mole ratio Cr : org. compd. = 1 : 1); soln. heated at ca. 55 °C for 5-7 h; soln. concd. at 50 °C and passed through a colomn; ethanol addedto eluate; resulting ppt. filtered, washed (EtOH), and dried over silica gel; elem. anal.;

cis-[chromium(1,2-diaminoethane)2Cl2]Cl + cytidine-5'-monophosphate disodium salt (6757-06-8) → Cr(3+)*NH2CH2CH2NH2*CONC(NH2)CHCHN(CHCHOHCHOHCH(CH2OPO3)O)(2-)*CONC(NH2)CHCHN(CHCHOHCHOHCH(CH2OPO3H)O)(1-)*C2H5OH*6H2O

Conditions	Yield
In water aq. soln. of Cr compd. mixed with aq. soln. of org. compd. (mole ratio Cr : org. compd. = 1 : 1); soln. heated at ca. 55 °C for 5-7 h; soln. concd. at 50 °C and passed through a colomn; ethanol addedto eluate; resulting ppt. filtered, washed (EtOH), and dried over silica gel; elem. anal.;

pentaaminechlorocobalt(III) dichloride (13859-51-3) + cytidine-5'-monophosphate disodium salt (6757-06-8) → (Co(NH3)4(NH2C4H2ON2C4H4(OH)2OCH2PO4H)2)(1+)*Cl(1-)*2H2O=(Co(NH3)4(NH2C4H2ON2C4H4(OH)2OCH2PO4H)2)Cl*2H2O

Conditions	Yield
With H2O; HClO4 In water Co-compd. (1 mmol) was dissolved in the min. amt. of H2O and 1 mmol of org. compd. in H2O; both solns. were mixed and brought to pH 4.5 by means of HClO4; the resulting soln. was concd. at 70°C for 5 min, then heated at 50°C for 20 h;; column chromy., the first fraction was pptd. with EtOH; the complex waswashed with ethanol and dried over P4O10; elem. anal.;;

trans-dichlorobis(ethylenediamine)cobalt(III) chloride (13408-72-5, 14040-32-5, 14040-33-6, 20594-10-9, 20594-11-0) + cytidine-5'-monophosphate disodium salt (6757-06-8) → (Co(NH2CH2CH2NH2)2(NH2C4H2ON2C4H4(OH)2OCH2PO4)(NH2C4H2ON2C4H4(OH)2OCH2PO4H))*6H2O

Conditions	Yield
With H2O In water Co-compd. (0.5 mmol) was dissolved in H2O and 1 mmol of org. compd. in H2O; both solns. were mixed and heated at 50°C with const. stirring for about 7 h;; column chromy., the first fraction was pptd. with EtOH; the complex waswashed with ethanol and dried over P4O10; elem. anal.;;

[(η6-biphenyl)(ethylenediamine)chlororuthenium(II)] hexafluorophosphate + cytidine-5'-monophosphate disodium salt (6757-06-8) → (C6H5C6H5)Ru(H2NCH2CH2NH2)OPO3CH2C4H4O(OH)2C4H2N2(NH2)(O) + (C6H5C6H5)Ru(H2NCH2CH2NH2)(OPO3CH2C4H4O(OH)2C4H2N2(NH2)(O))

Conditions	Yield
With H2O In water pH 7.23, 310 K, 3 d; reaction was monitored by (1)H and (31)P NMR spectroscopy; (1)H and (31)P NMR data;

deuteriated sodium hydroxide (14014-06-3) + uranyl nirate hexahydrate + cytidine-5'-monophosphate disodium salt (6757-06-8) → (UO2(cytidine monophosphate(4-)))3(O)(8-) + (UO2)6(cytidine monophosphate(4-))4(OH)2(O)2(10-)

Conditions	Yield
In water; water-d2 concd. NaOD soln. added to stirred suspn. of Na salt of nucleotide and UO2(NO2)2*6H2O in H2O-D2O; pH 8.5-12; not isoalted; detd. by NMR spectra; two UO2 complexes obtained in soln.;
In water-d2 concd. NaOD soln. added to stirred suspn. of Na salt of nucleotide and UO2(NO2)2*6H2O in D2O; pH 8.5-12; not isoalted; detd. by NMR spectra; two UO2 complexes obtained in soln.;

disodium[(bis(5-sulfosalicylaldehyde)-4,5-dimethyl-o-phenylenediiminato)cobalt(II)] + cytidine-5'-monophosphate disodium salt (6757-06-8) → disodium[(bis(5-sulfosalicylaldehyde)-4,5-dimethyl-o-phenylenediiminato)cobalt(II)]*cytidine-5'-monophosphate disodium salt

Conditions	Yield
With potassium nitrate In water (N2); mixing cobalt complex and AMP in 0.2 M aq. KNO3 at pH 7.0; not isolated, detected by UV;

disodium[(bis(4-methoxy-5-sulfosalicylaldehyde)-4,5-dimethyl-o-phenylenediiminato)cobalt(II)] + cytidine-5'-monophosphate disodium salt (6757-06-8) → disodium[(bis(4-methoxy-5-sulfosalicylaldehyde)-4,5-dimethyl-o-phenylenediiminato)cobalt(II)]*cytidine-5'-monophosphate disodium salt

Conditions	Yield
With potassium nitrate In water (N2); mixing cobalt complex and AMP in 0.2 M aq. KNO3 at pH 7.0; not isolated, detected by UV;

cytidine-5'-monophosphate disodium salt (6757-06-8) → P1-cytidine-P2-adenosine-5’-diphosphate disodium

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / acetonitrile / 0.18 h / 0 - 20 °C / Inert atmosphere 2.1: triethylamine / acetonitrile / 0.17 h / 0 °C / Inert atmosphere 3.1: N,N-dimethyl-formamide / Molecular sieve; Inert atmosphere 3.2: Dowex-50-W ion-exchange resin, Na+ form View Scheme

cytidine-5'-monophosphate disodium salt (6757-06-8) → C17H16F6N5O9P

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / acetonitrile / 0.18 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / acetonitrile / 0.17 h / 0 °C / Inert atmosphere View Scheme

cytidine-5'-monophosphate disodium salt (6757-06-8) → P1-uridine-P2-cytidine-5’-diphosphate disodium

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / acetonitrile / 0.18 h / 0 - 20 °C / Inert atmosphere 2.1: triethylamine / acetonitrile / 0.17 h / 0 °C / Inert atmosphere 3.1: N,N-dimethyl-formamide / Molecular sieve; Inert atmosphere 3.2: Dowex-50-W ion-exchange resin, Na+ form View Scheme

cytidine-5'-monophosphate disodium salt (6757-06-8) → P(1)-cytidine-P(3)-uridine-5'-triphosphate trisodium salt

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / acetonitrile / 0.18 h / 0 - 20 °C / Inert atmosphere 2.1: triethylamine / acetonitrile / 0.17 h / 0 °C / Inert atmosphere 3.1: N,N-dimethyl-formamide / Molecular sieve; Inert atmosphere 3.2: Dowex-50-W ion-exchange resin, Na+ form View Scheme

cytidine-5'-monophosphate disodium salt (6757-06-8) + trifluoroacetic anhydride (407-25-0) → C13H12F6N3O10P

Conditions	Yield
With triethylamine In acetonitrile at 0 - 20℃; for 0.183333h; Inert atmosphere;

Downstream Products

• 2906-23-2 CDP-glucose 

Relevant articles and documents

Phosphorylation, oligomerization and self-assembly in water under potential prebiotic conditions

Prebiotic phosphorylation of (pre)biological substrates under aqueous conditions is a critical step in the origins of life. Previous investigations have had limited success and/or require unique environments that are incompatible with subsequent generation of the corresponding oligomers or higher-order structures. Here, we demonstrate that diamidophosphate (DAP) - a plausible prebiotic agent produced from trimetaphosphate - efficiently (amido)phosphorylates a wide variety of (pre)biological building blocks (nucleosides/tides, amino acids and lipid precursors) under aqueous (solution/paste) conditions, without the need for a condensing agent. Significantly, higher-order structures (oligonucleotides, peptides and liposomes) are formed under the same phosphorylation reaction conditions. This plausible prebiotic phosphorylation process under similar reaction conditions could enable the systems chemistry of the three classes of (pre)biologically relevant molecules and their oligomers, in a single-pot aqueous environment.