Name: Cytidylic acid
SKU: 63-37-6

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Basic Information

Molecular Structure:
CAS No.:	63-37-6
Name:	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:	Xn,Xi
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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;

...Expand

: 69673-09-2
cytidine-5'-phosphoro-(2-aminoimidazole)

A: 63-37-6
cytidine monophosphate

B: 63-38-7
cytidine diphosphate

Conditions

Conditions	Yield
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

Conditions	Yield
In water at 20℃; Rate constant; Equilibrium constant; pH 8.5-8.7;

...Expand

: 623-27-8
terephthalaldehyde,

: 160984-91-8
C9H15N3O8P

A: 63-37-6
cytidine monophosphate

B: 623-27-8
Benzene-1,4-dicarbaldehyde

Conditions

Conditions	Yield
In water at 20℃; Rate constant; pH 8.5-8.7;

...Expand

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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.

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Consensus Reports

Specification