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Guanosine
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Name

Guanosine

 EINECS 204-227-8
CAS No. 118-00-3 Density 2.258 g/cm3
PSA 159.51000 LogP -2.10550
Solubility 0.75 g/L (25 °C) in water Melting Point 250 °C (dec.)(lit.)
Formula C10H13N5O5 Boiling Point 775.9°C at 760 mmHg
Molecular Weight 283.244 Flash Point 423.1oC
Transport Information UN 2811 6.1/PG 3 Appearance crystalline
Safety 45-24/25-23 Risk Codes 25
Molecular Structure Molecular Structure of 118-00-3 (Guanosine) Hazard Symbols ToxicT,IrritantXi
Synonyms

Inosine, 2-amino-;2-amino-9-pentofuranosyl-9H-purin-6-ol;Ribofuranoside, guanine-9, .beta.-D-;Guanine, 9-.beta.-D-ribofuranosyl-;D-Guanosine;Guanosine(GR);2-Amino-1,9-dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one;Guo;Guanine-9-beta-D-ribofuranoside;2H-Purin-2-one,6-amino-1,3-dihydro-;beta-D-Ribofuranoside, guanine-9;2(3H)-Imino-9-.beta.-D-ribofuranosyl-9H-purin-6(1H)-one;9-beta-D-Ribofuranosylguanine;9H-purin-6-ol, 2-amino-9-pentofuranosyl-;9-(beta-D-Ribofuranosyl)guanine;2-Amino-9-.beta.-D-ribofuranosyl-9-H-purine-6(1H)-one;

Article Data 143

Guanosine Synthetic route

2-N-(N,N-dibenzylformamidino)-9-(2,3-O-benzylidene-β-D-ribofuranosyl)-guanine

118-00-3

G

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal; palladium hydroxide - carbon In water; tert-butyl alcohol at 20℃; under 2068.59 Torr; for 20h; Hydrogenolysis;99%

2',3'-O-benzylidene-2N-dimethylaminomethylene guanosine

118-00-3

G

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal; palladium hydroxide - carbon In water; tert-butyl alcohol at 20℃; under 2068.59 Torr; for 20h; Hydrogenolysis;98%
100313-43-7

N-2-(ethoxycarbonyl)guanosine

118-00-3

G

Conditions
ConditionsYield
With pyridine; ammonium hydroxide at 45℃; for 48h;95%

9-(2',3'-di-O-acetyl-β-D-ribofuranosyl)-N2-isobutanoylguanine

118-00-3

G

Conditions
ConditionsYield
With ammonia In methanol at 25 - 28℃; for 10h;90%
6979-94-8

2',3',5'-tri-O-acetyl-guanosine

118-00-3

G

Conditions
ConditionsYield
With methanol; water; triethylamine at 71℃; Microwave irradiation;89%
41623-91-0

2-bromo-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)hypoxanthine

118-00-3

G

Conditions
ConditionsYield
With ammonia In methanol at 120℃;80%
With ammonium hydroxide at 150℃; for 3h;48%

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-diphenylcarbamoyloxy-2-isobutyrylamino-purin-9-yl)-tetrahydro-furan-3-yl ester

118-00-3

G

Conditions
ConditionsYield
With methanol; ammonia for 24h; Ambient temperature;80%
112233-75-7

2-(acetylamino)-6-(diphenylcarbamoyloxy)-9-(β-D-tri-O-acetylribofuranosyl)-9H-purine

118-00-3

G

Conditions
ConditionsYield
With ammonia In methanol; water at 60℃;75%
With methanol; ammonia for 24h; Ambient temperature;75%
58917-66-1

2',1''-anhydro-5-<(1''-benzamido-1''-hydroxymethylene)amino>-1-(β-D-ribofuranosyl)imidazole-4-carboxamide

A

118-00-3

G

B

[1-(15)N]guanosine

C

103654-70-2

<15NH2>guanosine

Conditions
ConditionsYield
With (15N)-ammonium chloride In dimethyl sulfoxide at 100℃; for 240h; Yields of byproduct given;A n/a
B 75%
C n/a
With (15N)-ammonium chloride In dimethyl sulfoxide at 100℃; for 240h; Yield given. Yields of byproduct given;
26001-38-7

8-mercaptoguanosine

118-00-3

G

Conditions
ConditionsYield
With potassium bromide In water at 20℃; pH=7; Reagent/catalyst; Inert atmosphere; Irradiation;57.4%
Multi-step reaction with 3 steps
1: dihydrogen peroxide; acetic acid / 48 h / 65 °C
2: lithium hydroxide; water-d2 / Sonication
3: 24 h / 50 °C
View Scheme

Guanosine Consensus Reports

Reported in EPA TSCA Inventory.

Guanosine Specification

The Guanosine, with the CAS registry number 118-00-3 and EINECS registry number 204-227-8, has the IUPAC name of 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one. It belongs to the following product categories: Pharmaceutical Intermediates; Purine; API intermediates; Biochemistry; Nucleosides and their analogs; Nucleosides, Nucleotides & Related Reagents; Bases & Related Reagents. And the molecular formula of the chemical is C10H13N5O5.

The Guanosine is a purine nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a -N9-glycosidic bond, and is required for an RNA splicing reaction in mRNA. What's more, it is always used in herpes treatment.

The physical properties of Guanosine 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): 1.284; (5)ACD/KOC (pH 7.4): 1.278; (6)#H bond acceptors: 10; (7)#H bond donors: 6; (8)#Freely Rotating Bonds: 5; (9)Polar Surface Area: 155.22 Å2; (10)Index of Refraction: 1.955; (11)Molar Refractivity: 60.811 cm3; (12)Molar Volume: 125.448 cm3; (13)Polarizability: 24.107×10-24cm3; (14)Surface Tension: 123.824 dyne/cm; (15)Density: 2.258 g/cm3. 

You should be cautious while dealing with this chemical. It is toxic if swallowed. Therefore, you had better take the following instructions: Avoid contact with skin and eyes; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible); Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer).

You can still convert the following datas into molecular structure:
(1)SMILES: c1nc2c(=O)[nH]c(nc2n1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N
(2)InChI: InChI=1/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1
(3)InChIKey: NYHBQMYGNKIUIF-UUOKFMHZBU

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 intravenous 180mg/kg (180mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03206,

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