Name: Cytidine
SKU: 65-46-3

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Basic Information

Molecular Structure:
CAS No.:	65-46-3
Name:	Cytidine

Formula:	C₉H₁₃N₃O₅
Molecular Weight:	243.219
Synonyms:	Cytosine riboside;1-.beta.-D-Ribofuranosylcytosine;4-Amino-1.beta.-D-ribofuranosyl-2(1H)-pyrimidinone;beta-D-Ribofuranoside, cytosine-1;2(1H)-Pyrimidinone, 4-amino-1-beta-D-ribofuranosyl-;Cytosine, 1-beta-D-ribofuranosyl-;2(1H)-Pyrimidinone, 4-amino-1-.beta.-D-ribofuranosyl-;1.beta.-Ribofuranosylcytosine;1-beta-D-ribosyl- (6CI);1beta-2-Ribofuranosylcytosine, d-;4-Amino-1-beta-D-ribofuranosyl-2(1H)-pyrimidinone;cytosine-1;CP-C;1-(beta-D-Ribofuranosyl)-2-oxo-4-amino-1,2-dihydro-1,3-diazine;Cytidine(CR);Cytosine nucleoside(Cytidine);
EINECS:	200-610-9
Density:	1.89 g/cm³
Melting Point:	210-217 °C
Boiling Point:	545.7 °C at 760 mmHg
Flash Point:	283.8 °C
Solubility:	50 mg/mL in water
Appearance:	White crystalline powder
Risk Codes:	68
Safety:	24/25
PSA:	130.83000
LogP:	-1.98180

Synthetic route

: 4N-dimethylaminomethylene cytidine

: 65-46-3
CYTIDINE

Conditions

Conditions	Yield
In methanol; water at 50℃; for 36h; Hydrolysis;	99%

: 4N-dibenzylaminomethylene cytidine

: 65-46-3
CYTIDINE

Conditions

Conditions	Yield
In methanol; water at 50℃; for 26h; Hydrolysis;	99%

: 5040-18-6
4-N-2',3',5'-O-tetraacetylcytidine

: 65-46-3
CYTIDINE

Conditions

Conditions	Yield
With sodium methylate; guanidine nitrate In methanol; dichloromethane at 0℃; for 0.166667h;	95%
With methanol; water; triethylamine at 71℃; for 0.75h;	92%

: 56787-28-1
2',3',5'-tri-O-acetylcytidine

: 65-46-3
CYTIDINE

Conditions

Conditions	Yield
With ammonia In dichloromethane at 25℃;	93%
With ammonia In methanol at 25℃; for 24h; Yield given;
In ammonium hydroxide Yield given;

: 6-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6H-tetrazolo[1,5-c]pyrimidin-5-one

: 65-46-3
CYTIDINE

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol for 10h;	89%

: 473910-24-6
[1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-carbamic acid 2-nitro-benzyl ester

: 65-46-3
CYTIDINE

Conditions

Conditions	Yield
In 1,4-dioxane; water for 1.16667h; UV-irradiation;	89%

: 10578-79-7
4-methylamino-1-(β-D-ribofuranosyl)pyrimidin-2(1H)-one

: 65-46-3
CYTIDINE

Conditions

Conditions	Yield
With manganese(IV) oxide; C17H20N4O9P(1-)*Na(1+); oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 7h; Irradiation; chemoselective reaction;	89%

: 2,2'-anhydrocytidine hydrochloride

: 65-46-3
CYTIDINE

Conditions

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 105℃; for 3h;	80.9%

: 800379-05-9
1-(3,4-dihydroxy-5-hydroxymethyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 4-(O-benzyloxime)

A: 3258-02-4
uridine 4-oxime

B: 65-46-3
CYTIDINE

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 60℃; for 1h;	A 22% B 77%

: 4-Amino-1-((4aR,6R,7R,7aR)-7-hydroxy-2-oxo-tetrahydro-2λ4-furo[3,2-d][1,3,2]dioxathiin-6-yl)-1H-pyrimidin-2-one

: 65-46-3
CYTIDINE

Conditions

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide	76.5%

Raw Materials

Downstream Products

65-47-4

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The IUPAC name of Cytidine is 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one. With the CAS registry number 65-46-3, it is also named as 1-beta-D-Ribofuranosylcytosine. The product's categories are Pharmaceutical Intermediates; Fine Chemical & Intermediates; Pyridines, Pyrimidines, Purines and Pteredines; Biochemistry; Nucleosides and their Analogs; Nucleosides, Nucleotides & Related Reagents; Nucleic Acids, and the other registry numbers are 4395-95-3; 494210-74-1; 873077-03-3. Besides, it is white crystalline powder, which should be stored in dark, dry and sealed place at room temperature. It is a component of RNA which is attached to a deoxyribose ring. In addition, this chemical is stable and incompatible with strong oxidizing agents.

Physical properties about Cytidine are: (1)ACD/LogP: -1.808; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -1.82; (4)ACD/LogD (pH 7.4): -1.81; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 2.39; (8)ACD/KOC (pH 7.4): 2.47; (9)#H bond acceptors: 8; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.756; (13)Molar Refractivity: 52.643 cm³; (14)Molar Volume: 128.433 cm³; (15)Polarizability: 20.869 10-24cm³; (16)Surface Tension: 89.588996887207 dyne/cm; (17)Density: 1.894 g/cm³; (18)Flash Point: 283.816 °C; (19)Enthalpy of Vaporization: 94.8 kJ/mol; (20)Boiling Point: 545.678 °C at 760 mmHg

Preparation of Cytidine: this chemical can be prepared by 1-(2',3',4'-Tri-O-benzoyl-a-D-xylofuranosyl)-4-thiouracil.

Preparation of Cytidine

This reaction needs Ammonia and Methanol at temperature of 100 °C. The reaction time is 18 hours. The yield is 76 %.

Uses of Cytidine: it is used for biochemical research and organic synthesis. It is also used for producing cytarabine, ring cell, and CTP, cytidine diphosphate choline, etc.

When you are using this chemical, please be cautious about it as the following: it is possible risk of irreversible effects. You should avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7-,8-/m1/s1;
(2)InChIKey=UHDGCWIWMRVCDJ-XVFCMESISA-N;
(3)Smilesn1([C@@H]2O[C@H](CO)[C@H]([C@H]2O)O)c(nc(N)cc1)=O

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	2700mg/kg (2700mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Russian Pharmacology and Toxicology Vol. 40, Pg. 66, 1977.

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Consensus Reports

Specification