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58-63-9

Basic Information
CAS No.: 58-63-9
Name: Inosine
Article Data: 92
Cas Database
Molecular Structure:
Molecular Structure of 58-63-9 (Inosine)
Formula: C10H12N4O5
Molecular Weight: 268.229
Synonyms: 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one;4-acetamidobenzoic acid; 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione; 9-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one; 1-dimethylaminopropan-2-ol;6-Hydroxy-9-(β-D-ribofuranosyl)-9H-purine;2',3',5'–Triacetylinosine;iso-prinosine;Inosine (8CI,9CI);hypoxanthine-ribose;.beta.-Inosine;Inosina [INN-Spanish];9-.beta.-D-Ribofuranosylhypoxanthine;Hypoxanthine 9-beta-D-ribofuranoside;Oxiamin;556-08-1;Hypoxanthine, 9-beta-D-ribofuranosyl-;Inosine-Pranobex;Ribonosine;(-)-Inosine;Inotin (TN);Hypoxanthine ribonucleoside;9H-purin-6-ol, 9-pentofuranosyl-;9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one;Inosine [INN:JAN];Atorel;9-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one;Inosine (JAN);1,9-Dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one;beta-D-Ribofuranoside, hypoxanthine-9;
EINECS: 200-390-4
Density: 2.085 g/cm3
Melting Point: 222-226 °C (dec.)(lit.)
Boiling Point: 732.815 °C at 760 mmHg
Flash Point: 396.993 °C
Solubility: 2.1 g/100 mL (20 °C) in water
Appearance: White crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 24/25-36-26
Transport Information: N/A
PSA: 133.49000
LogP: -2.26890
Synthetic route

Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-hydroxy-purin-9-yl)-tetrahydro-furan-3-yl ester

A

58-63-9

inosine

B

58-61-7

adenosine

Conditions
ConditionsYield
Multistep reaction;
58-61-7

adenosine

58-63-9

inosine

Conditions
ConditionsYield
With sodium phosphate buffer; adenosine deaminase In water at 27℃; pH=7.5; Enzyme kinetics;
With adenosine deaminase Kinetics; Concentration; Enzymatic reaction;
Multi-step reaction with 2 steps
1: purine nucleoside phosphorylase from aeromonas hydrophila II / aq. phosphate buffer / 20 °C / pH 7.5 / Enzymatic reaction
2: aq. phosphate buffer / 20 °C / pH 7.5
View Scheme
With adenine deaminase from E. coli; water In aq. phosphate buffer at 25℃; pH=7.0; Catalytic behavior; Reagent/catalyst; Enzymatic reaction;
Conditions
ConditionsYield
With recombinant nucleoside acid phosphatase/phosphotransferase from Escherichia blattae at 30℃; for 0.166667h; pH=5; Kinetics; Time; pH-value; Temperature; Reagent/catalyst; aq. acetate buffer;
58-96-8

uridine

58-63-9

inosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium phosphate; recombinant Escherichia coli uridine phosphorylase / water / 72 h / 50 °C / pH 7 / Enzymatic reaction
1.2: 24 h / 4 °C
2.1: recombinant Escherichia coli purine nucleoside phosphorylase / 20 °C / pH 7 / Enzymatic reaction
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: purine nucleoside phosphorylase from aeromonas hydrophila II / aq. phosphate buffer / 20 °C / pH 7.5 / Enzymatic reaction
2: aq. phosphate buffer / 20 °C / pH 7.5
View Scheme
99790-49-5

α-D-ribose-1-phosphate

58-63-9

inosine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. phosphate buffer / 20 °C / pH 7.5
2: purine nucleoside phosphorylase from aeromonas hydrophila II / aq. phosphate buffer / 20 °C / pH 7.5 / Enzymatic reaction
3: aq. phosphate buffer / 20 °C / pH 7.5
View Scheme
Multi-step reaction with 3 steps
1: aq. phosphate buffer / 20 °C / pH 7.5
2: purine nucleoside phosphorylase from aeromonas hydrophila II / aq. phosphate buffer / 20 °C / pH 7.5 / Enzymatic reaction
3: aq. phosphate buffer / 20 °C / pH 7.5
View Scheme
99790-49-5

α-D-ribose-1-phosphate

58-63-9

inosine

Conditions
ConditionsYield
In aq. phosphate buffer at 20℃; pH=7.5;

α-D-ribofuranose-1-O-phosphate barium salt

68-94-0

6-hydroxypurine

58-63-9

inosine

Conditions
ConditionsYield
With recombinant Escherichia coli purine nucleoside phosphorylase at 20℃; pH=7; Kinetics; Reagent/catalyst; Enzymatic reaction;
68-94-0

6-hydroxypurine

58-96-8

uridine

58-63-9

inosine

Conditions
ConditionsYield
With recombinant Escherichia coli purine nucleoside phosphorylase; recombinant Escherichia coli uridine phosphorylase at 20℃; pH=7; Enzymatic reaction;
68-94-0

Allopurinol

58-96-8

uridine

58-63-9

inosine

Conditions
ConditionsYield
With Clostridium perfringens uridine phosphorylase; Aeromonas hydrophila purine nucleosidephosphorylase co-immobilized on glyoxyl-agarose In aq. phosphate buffer at 28℃; under 1034.32 Torr; pH=7.5; Flow reactor; Green chemistry; Enzymatic reaction;
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Inosine, with the CAS registry number 58-63-9 and EINECS registry number 200-390-4, has the IUPAC name of 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one. It is a kind of white crystalline powder, and belongs to the following product categories: Nucleotides and Nucleosides; Antivirals for Research and Experimental Use; Biochemistry; Nucleosides, Nucleotides & Related Reagents; Nucleic acids; Bases & Related Reagents. And the molecular formula of the chemical is C10H12N4O5.

The Inosine can be found in tRNAs and is essential for proper translation of the genetic code in wobble base pairs. It is an intermediate in a chain of purine nucleotides reactions required for muscle movements. And it has neuroprotective properties. Besides, it is classified as an antiviral in the Anatomical Therapeutic Chemical Classification System. What's more, it can be produced by Straight-Dough Method.

The physical properties of Inosine 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): 2.004; (5)ACD/KOC (pH 7.4): 2.02; (6)#H bond acceptors: 9; (7)#H bond donors: 4; (8)#Freely Rotating Bonds: 5; (9)Polar Surface Area: 129.2 Å2; (10)Index of Refraction: 1.879; (11)Molar Refractivity: 58.896 cm3; (12)Molar Volume: 128.666 cm3; (13)Polarizability: 23.348×10-24cm3; (14)Surface Tension: 104.426 dyne/cm; (15)Density: 2.085 g/cm3; (16)Flash Point: 396.993 °C; (17)Enthalpy of Vaporization: 112.251 kJ/mol; (18)Boiling Point: 732.815 °C at 760 mmHg; (19)Vapour Pressure: 0 mmHg at 25°C.

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: Avoid contact with skin and eyes. Wear suitable protective clothing, and if 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: c1[nH]c2c(c(=O)n1)ncn2[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O
(2)InChI: InChI=1/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1
(3)InChIKey: UGQMRVRMYYASKQ-KQYNXXCUBA

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 3175mg/kg (3175mg/kg)   Pharmaceutical Chemistry Journal Vol. 20, Pg. 160, 1986.
mouse LD50 intravenous > 2800mg/kg (2800mg/kg)   Drugs in Japan Vol. -, Pg. 156, 1995.
mouse LD50 oral > 20gm/kg (20000mg/kg)   Drugs in Japan Vol. 6, Pg. 77, 1982.
mouse LD50 subcutaneous 5gm/kg (5000mg/kg)   Drugs in Japan Vol. 6, Pg. 77, 1982.
rat LD50 intraperitoneal 2900mg/kg (2900mg/kg)   Drugs in Japan Vol. 6, Pg. 77, 1982.
rat LD50 intravenous > 2gm/kg (2000mg/kg)   Drugs in Japan Vol. 6, Pg. 77, 1982.
rat LD50 oral > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. -, Pg. 156, 1995.