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63-37-6

Basic Information
CAS No.: 63-37-6
Name: Cytidylic acid
Article Data: 57
Molecular Structure:
Molecular Structure of 63-37-6 (Cytidylic acid)
Formula: C9H14N3O8P
Molecular Weight: 323.199
Synonyms: Cytidine monophosphate;Cytidine 5'-phosphoric acid;Cytidine 5'-phosphate;Cytidine 5'-monophosphoric acid;Cytidine, mono(dihydrogenphosphate) (ester);Cytosine 5'-monophosphate;Cytidine 5'-(dihydrogen phosphate);CMP (nucleotide);5'-CMP;5'-Cytidylic acid;
EINECS: 200-556-6
Density: 2.155 g/cm3
Melting Point: ~222°C (dec.)
Boiling Point: 678.086 °C at 760 mmHg
Flash Point: 363.893 °C
Solubility: soluble
Appearance: white crystalline powder
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 20/21/22-36/37/38
Safety: 24/25-37/39-36-26
PSA: 187.17000
LogP: -1.86480
Synthetic route
65-46-3

CYTIDINE

63-37-6

cytidine monophosphate

Conditions
ConditionsYield
Stage #1: CYTIDINE With trichlorophosphate at 20℃; for 0.1h; Flow reactor; Green chemistry;
Stage #2: With water at 20℃; Temperature; Flow reactor; Green chemistry; chemoselective reaction;
94%
With tris(p-nitrophenyl)phosphate at 50℃; Erwina herbicola 47/3 cells;84%
With triethyl phosphate; trichlorophosphate In water at 0℃; for 5h; Rate constant; Product distribution; var. reaction conditions;83 % Chromat.
69673-09-2

cytidine-5'-phosphoro-(2-aminoimidazole)

A

63-37-6

cytidine monophosphate

B

68521-86-8

cytidine 5'-fluorophosphate

Conditions
ConditionsYield
With water; lithium fluoride at 25℃; pH=8.6; Reagent/catalyst; pH-value;A 14.2%
B 85.4%
538-37-4

dibenzyl phosphochloridate

362-42-5

2',3'-O-isopropylidenecytidine

63-37-6

cytidine monophosphate

Conditions
ConditionsYield
With pyridine Hydrierung des Reaktionsprodukts an Palladium in wss.Aethanol und anschliessend Hydrolyse mit wss.H2SO4;
362-42-5

2',3'-O-isopropylidenecytidine

63-37-6

cytidine monophosphate

Conditions
ConditionsYield
With phosphoric acid; water; phosphorus pentoxide und anschliessend mit H2O;
Multi-step reaction with 2 steps
1: H3PO4; N-butylimidazole; Bu3N / dimethylformamide; various solvent(s) / 6 h / Heating
2: DOWEX(R) 50WX2-200
View Scheme
Multi-step reaction with 3 steps
1: 91 percent / t-butylmagnesium chloride / tetrahydrofuran / 1 h / Ambient temperature
2: Pd(P(C6H5)3)4, P(C6H5)3, HCOOH, n-C4H9NH2 / tetrahydrofuran / 5.7 h / 50 °C
3: 2 N aq. HCl / 12 h / 25 °C
View Scheme
538-37-4

dibenzyl phosphochloridate

3257-72-5, 7558-02-3

O2',O3'-((R)-benzylidene)-cytidine

63-37-6

cytidine monophosphate

Conditions
ConditionsYield
With pyridine Hydrierung des Reaktionsprodukts an Palladium in wss.Aethanol und anschliessend Hydrolyse mit wss.H2SO4;
3257-72-5, 7558-02-3

O2',O3'-((R)-benzylidene)-cytidine

63-37-6

cytidine monophosphate

Conditions
ConditionsYield
With phosphoric acid; water; phosphorus pentoxide und anschliessend mit H2O;
With pyridine; trichlorophosphate und Erhitzen des Reaktionsprodukts mit wss.H2SO4;
110-91-8

morpholine

30784-94-2

cytidine-5'-phosphodichloride

A

122450-01-5

cytidine-5'-phosphodimorpholide

B

63-37-6

cytidine monophosphate

C

76742-17-1

cytidine 5'-monophosphate morpholidate

Conditions
ConditionsYield
With water 1.) triethyl phosphate, 5-7 deg C, 60 min, 2.) 5-7 deg C, 7 h; Yield given. Multistep reaction. Yields of byproduct given;
With water 1.) triethyl phosphate, 5-7 deg C, 120 min, 2.) methanol, 5-7 deg C, 7 h; Yield given. Multistep reaction. Yields of byproduct given;
With water 1.) triethyl phosphate, 5-7 deg C, 10 min, 2.) methanol, 5-7 deg C, 7 h; Yield given. Multistep reaction. Yields of byproduct given;
69673-09-2

cytidine-5'-phosphoro-(2-aminoimidazole)

A

63-37-6

cytidine monophosphate

B

63-38-7

cytidine diphosphate

Conditions
ConditionsYield
With phosphate buffer; sodium chloride at 37℃; Rate constant; Product distribution; Mechanism;
5746-18-9

1-methyl-4-carboxypyridinium chloride

160984-91-8

C9H15N3O8P

A

36455-39-7

C7H8NO2

B

63-37-6

cytidine monophosphate

Conditions
ConditionsYield
In water at 20℃; Rate constant; Equilibrium constant; pH 8.5-8.7;
623-27-8

terephthalaldehyde,

160984-91-8

C9H15N3O8P

A

63-37-6

cytidine monophosphate

B

623-27-8

Benzene-1,4-dicarbaldehyde

Conditions
ConditionsYield
In water at 20℃; Rate constant; pH 8.5-8.7;
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The 5'-Cytidylic acid, with the CAS registry number 63-37-6 and EINECS registry number 200-556-6, is also known as CMP. It is a kind of white crystalline powder, and belongs to the following product categories: Pharmaceutical Intermediates; Nucleotides and Nucleic Acids; Heterocyclic Compounds; Biochemistry; Nucleosides, Nucleotides & Related Reagents; Nucleotides and their analogs. And the molecular formula of the chemical is C9H14N3O8P. What's more, while dealing with this chemical, you should avoid contacting with skin and eyes. It is always used as material and intermediate to produce Nucleotides and Nucleic Acids, and it is also used as food additive and pharmaceutical material.

It is a nucleotide which can be found in RNA. It is an ester of phosphoric acid with the nucleoside cytidine. And it consists of the phosphate group, the pentose sugar ribose, and the nucleobase cytosine; hence, a ribonucleoside monophosphate. What's more, it can be phosphorylated to Cytidine diphosphate by the enzyme CMP kinase, with Adenosine triphosphate or guanine triphosphate donating the phosphate group.

The physical properties of 5'-Cytidylic acid are as followings: (1)# of Rule of 5 Violations: 2; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 11; (7)#H bond donors: 6; (8)#Freely Rotating Bonds: 6; (9)Polar Surface Area: 184.95 Å2; (10)Index of Refraction: 1.775; (11)Molar Refractivity: 62.593 cm3; (12)Molar Volume: 149.953 cm3; (13)Polarizability: 24.814×10-24cm3; (14)Surface Tension: 121.559 dyne/cm; (15)Density: 2.155 g/cm3; (16)Flash Point: 363.893 °C; (17)Enthalpy of Vaporization: 113.869 kJ/mol; (18)Boiling Point: 678.086 °C at 760 mmHg; (19)Vapour Pressure: 0 mmHg at 25°C. 

You can still convert the following datas into molecular structure:
(1)SMILES: c1cn(c(=O)nc1N)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O
(2)InChI: InChI=1/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
(3)InChIKey: IERHLVCPSMICTF-XVFCMESIBY

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD intraperitoneal > 1gm/kg (1000mg/kg)   Annals of the New York Academy of Sciences. Vol. 60, Pg. 251, 1954.