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Uridine
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Name

Uridine

 EINECS 200-407-5
CAS No. 58-96-8 Density 1.675 g/cm3
PSA 124.78000 LogP -2.85190
Solubility 50 mg/mL in water Melting Point 163-167 °C(lit.)
Formula C9H12N2O6 Boiling Point 387.12°C (rough estimate)
Molecular Weight 244.204 Flash Point N/A
Transport Information N/A Appearance white to off-white crystalline powder
Safety 24/25-36-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 58-96-8 (Uridine) Hazard Symbols IrritantXi
Synonyms

1-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H- pyrimidine-2,4-dione;1-[(3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione;beta-D-Ribofuranoside;2,4(1H,3H)-pyrimidinedione-1;1-beta-D-ribofuranosyl- (7CI);Uridine & 3-Azido-3-deoxythymidine;1-[(2S,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione;2,4(1H,3H)-pyrimidinedione, 1-beta-D-ribofuranosyl-;1-beta-D-Ribofuranosyluracil;1-.beta.-D-Ribofuranosyluracil & Thymidine, 3-azido-3-deoxy-;Uridin;Uracil, 1-.beta.-D-ribofuranosyl-;Uracil, 1-beta-L-ribofuranosyl-;

Article Data 229

Uridine Synthetic route

6554-10-5

5'-O-trityluridine

58-96-8

uridine

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate; silica gel In dichloromethane at 25℃; for 1.5h; detritylation;98%
With iodine(I) bromide In methanol; dichloromethane at 20℃; for 0.0833333h; chemoselective reaction;95%
Stage #1: 5'-O-trityluridine With carbon tetrabromide In methanol for 0.5h; Irradiation;
Stage #2: In methanol at 20℃; for 11.5h;		94%
1748-04-5

tribenzoyl uridine

58-96-8

uridine

Conditions
ConditionsYield
With methanol; ammonia at 20℃;91%
With methanol; sodium methylate at 20℃; for 2h;87%
With triethylamine In methanol; water83%
With sodium methylate In methanol Ambient temperature;
64898-15-3

2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine

58-96-8

uridine

Conditions
ConditionsYield
With SO3H silica gel In ethyl acetate at 20℃; for 15h;81%
65-46-3

CYTIDINE

58-96-8

uridine

Conditions
ConditionsYield
With cytidine deaminase enzyme In aq. phosphate buffer at 37℃; for 0.0833333h; pH=7; Enzymatic reaction;99%
With oxygen; nitrogen(II) oxide In dimethyl sulfoxide for 1h; Ambient temperature;47%
With sodium hydroxide at 90.1℃; Rate constant; Mechanism; various reagent concentration, decomposition to nonchromophoric products;
362-43-6

2',3'-O-isopropylideneuridine

58-96-8

uridine

Conditions
ConditionsYield
With indium(III) triflate In water; acetonitrile at 120℃; for 0.0833333h; Microwave irradiation;98%
With K 10 clay In methanol; water at 75℃; for 26h;94%
With trifluoroacetic acid Yield given;
With erbium(III) triflate In water at 120℃; for 0.0833333h; Microwave irradiation;99 % Chromat.
With Pd(OH)2/C; cyclohexene In methanol for 3h; Reflux;
69304-38-7

3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

58-96-8

uridine

Conditions
ConditionsYield
With K 10 clay In methanol; water at 75℃; for 36h;97%
Multi-step reaction with 3 steps
1: 71 percent / triethylamine / 17 h / Ambient temperature
2: 70 percent / 1M tributylammonium fluoride (TBAHF) / tetrahydrofuran / 4 h / Ambient temperature
3: 95 percent / triphenylmethyl fluoroborate / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: boron trifluoride diethyl etherate / 1,2-dichloro-ethane / 2 h / 20 °C / Molecular sieve
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h
3: hydrogenchloride; water; lithium iodide / acetonitrile
View Scheme
Reaxys ID: 11351538

Reaxys ID: 11351538

58-96-8

uridine

Conditions
ConditionsYield
With Levalit MDS 1368 cation exchanger (Na-form) In water at 80℃;49%
4105-38-8

Tri-O-acetyluridine

58-96-8

uridine

Conditions
ConditionsYield
With methanol; water; triethylamine at 71℃; Microwave irradiation;93%
Multi-step reaction with 3 steps
1: triethylamine / tetrahydrofuran / 17 h / Ambient temperature
2: 78 percent / conc. NH4OH / methanol
3: 95 percent / triphenylmethyl fluoroborate / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme
With keratinase from Doratomyces microsporus Hydrolysis; Enzymatic reaction;
With ammonia In methanol at 20℃;
81246-79-9

5'-dimethoxytrityluridine

58-96-8

uridine

Conditions
ConditionsYield
With K 10 clay In methanol; water at 75℃; for 0.5h;96%
With iodine(I) bromide In methanol; dichloromethane at 20℃; for 0.0166667h; chemoselective reaction;95%
With cerium(IV) triflate; water In acetonitrile at 25℃; for 0.5h;93%
133766-24-2

2'-O-allyluridine

58-96-8

uridine

Conditions
ConditionsYield
With quinoline-2-carboxylic acid; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate In methanol at 30℃;99%
With hexaaquaruthenium(II) tosylate In water at 40℃; for 36h; Time;95%

Uridine Consensus Reports

Reported in EPA TSCA Inventory.

Uridine Specification

The Uridine, with the CAS registry number 58-96-8 and EINECS registry number 200-407-5, has the IUPAC name of 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione. It is a kind of white to slightly off-white powder, and belongs to the following product categories: Pyridines, Pyrimidines, Purines and Pteredines; Chiral; Biochemistry; Nucleosides and their analogs; Nucleosides, Nucleotides & Related Reagents; Nucleic acids. The molecular formula of the chemical is C9H12N2O6. What's more, it is a major material of some drugs, such as S-FC, IDUR, BDUR, etc. And it can be prepared by 2,4 - dichloro-(trimethylsiloxy) pyrimidine. 

The Uridine is one of the four basic components of RNA, and plays a role in the glycolysis pathway of galactose. There is no catabolic process to metabolize galactose. Therefore, galactose is converted to glucose and metabolized in the common glucose pathway.

The physical properties of Uridine are as followings: (1)# of Rule of 5 Violations: 0; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 3.288; (5)ACD/KOC (pH 7.4): 3.248; (6)#H bond acceptors: 8; (7)#H bond donors: 4; (8)#Freely Rotating Bonds: 5; (9)Polar Surface Area: 119.33 Å2; (10)Index of Refraction: 1.643; (11)Molar Refractivity: 52.732 cm3; (12)Molar Volume: 145.792 cm3; (13)Polarizability: 20.904×10-24cm3; (14)Surface Tension: 88.509 dyne/cm; (15)Density: 1.675 g/cm3. 

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Do not breathe dust and avoid contacting with skin and eyes; Wear suitable protective clothing, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cn(c(=O)[nH]c1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
(2)InChI: InChI=1/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1
(3)InChIKey: DRTQHJPVMGBUCF-XVFCMESIBG

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 4335mg/kg (4335mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)		 Journal of Pharmacology and Experimental Therapeutics. Vol. 207, Pg. 504, 1978.
 

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