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58-63-9

Basic Information
CAS No.: 58-63-9
Name: Inosine
Molecular Structure:
Molecular Structure of 58-63-9 (Inosine)
Formula: C10H12N4O5
Molecular Weight: 268.26
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:
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;
108-24-7

acetic anhydride

58-63-9

inosine

3181-38-2

2’,3’,5’-tri-O-acetylinosine

Conditions
ConditionsYield
With dmap; triethylamine In acetonitrile at 20℃;100%
With pyridine at 0℃; for 16h;
With dmap; triethylamine In acetonitrile for 1h;
58-63-9

inosine

7013-16-3

9-(β-D-arabinofuranosyl)-9H-purin-6(1H)-one

Conditions
ConditionsYield
With uridine phosphorylase; disodium hydrogen arsenate heptahydrate; Escherichia coli purine nucleoside phosphorylase for 48h; Enzymatic reaction;98%
103-84-4

Acetanilid

58-63-9

inosine

13035-61-5

1,2,3,5-tetraacetylribose

Conditions
ConditionsYield
With aluminum (III) chloride In methanol at 60℃; for 2h; Solvent; Temperature;95%
58-63-9

inosine

58479-61-1

tert-butylchlorodiphenylsilane

9-(2R,3R,4R,5R)-3,4-bis((tert-butyldiphenylsilyl)oxy)-5-((((tert-butyldiphenylsilyl)oxy)methyl)oxolan-2-yl)-9H-purin-6-ol

Conditions
ConditionsYield
With zinc(II) chloride; zinc In dichloromethane at 30 - 40℃; for 3h;94.7%
58-63-9

inosine

697807-01-5

C10H10(2)H2N4O5

Conditions
ConditionsYield
With hydrogen; water-d2; palladium 10% on activated carbon at 110 - 140℃; for 48h; Product distribution / selectivity;90%
108-05-4

vinyl acetate

58-63-9

inosine

28526-32-1

5'-O-acetylinosine

Conditions
ConditionsYield
With pyridine; Candida antarctica lipase at 60℃; for 24h;87%
927-49-1

dipentyl ketone

58-63-9

inosine

9-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dipentyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1,9-dihydro-6Hpurin-6-one

Conditions
ConditionsYield
With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 24h;87%
133360-56-2

propan-2-one O-butyryl oxime

58-63-9

inosine

145355-70-0

Butyric acid (2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester

Conditions
ConditionsYield
In tetrahydrofuran at 60℃; for 24h; Candida antarctica lipase (SP435);86%
108-05-4

vinyl acetate

58-63-9

inosine

A

Acetic acid (2R,3S,4R,5R)-4-hydroxy-2-hydroxymethyl-5-(6-hydroxy-purin-9-yl)-tetrahydro-furan-3-yl ester

B

Acetic acid (2R,3R,4R,5R)-4-hydroxy-5-hydroxymethyl-2-(6-hydroxy-purin-9-yl)-tetrahydro-furan-3-yl ester

Conditions
ConditionsYield
With Pseudomonas sp. lipase (Lipase PS) In tetrahydrofuran at 30℃; for 96h;A 83%
B n/a
145355-61-9

acetone oxime acrylate

58-63-9

inosine

145355-75-5

Acrylic acid (2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester

Conditions
ConditionsYield
In tetrahydrofuran at 60℃; for 15h; Candida antarctica lipase (SP435);80%
65-71-4

thymin

58-63-9

inosine

1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With potassium phosphate; xanthine oxidase; purine and pyrimidine nucleoside phosphorylase (PUNP, PYNP) at 40℃; for 11h;76%
With potassium phosphate; xanthine oxidase; PUNP, PYNP at 40℃; for 11h; Equilibrium constant;76%
123-19-3

4-heptanone

58-63-9

inosine

9-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dipropyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1,9-dihydro-6Hpurin-6-one

Conditions
ConditionsYield
With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 23h;69%
21434-62-8, 41475-72-3

cis-dichloro(DL-ethionine)platinum(II)

58-63-9

inosine

chloro(inosine)(DL-ethionine)platinum(II) chloride

Conditions
ConditionsYield
In water refluxed on a water bath for 3 h; soln. concd., cooled, filtered, filtrate kept in the refrigerator overnight, ppt. filtered off, washed with acetone, dried in vacuo; elem. anal.;68%
58-63-9

inosine

99790-49-5

α-D-ribose-1-phosphate

Conditions
ConditionsYield
In water at 60℃; for 3h; phosphate buffer pH 7.0; purine nucleoside phosphorylase of Enterobacter aerogenes AJ 11125;55%
With purine nucleoside phosphorylase from aeromonas hydrophila II In aq. phosphate buffer at 20℃; pH=7.5; Reagent/catalyst; Enzymatic reaction;
59278-00-1

2-acetoxyethyl acetoxymethyl ether

58-63-9

inosine

150581-50-3

9-((2-acetoxyethoxy)methyl)-hypoxanthine

Conditions
ConditionsYield
With p-toluenesulfonic acid monohydrate; acetic anhydride In acetonitrile47%
58-63-9

inosine

870-63-3

prenyl bromide

1237496-78-4

6-(3-methyl-2-butenyloxy)-9-(β-D-ribofuranosyl)purine

Conditions
ConditionsYield
With barium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; Darkness;46%
With barium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;
58-63-9

inosine

339091-09-7

9-(2-O-Triflyl-β-L-ribofuranosyl)hypoxanthine

Conditions
ConditionsYield
Stage #1: inosine With di(n-butyl)tin oxide In methanol Heating / reflux;
Stage #2: With trifluoromethane sulfonyl chloride In N,N-dimethyl-formamide at 20℃; for 1h;
37%
58-63-9

inosine

5965-66-2

LACTOSE

C16H22N4O10

Conditions
ConditionsYield
With β-galactosidase from Bacillus megaterium YZ08 In dimethyl sulfoxide at 35℃; Solvent; Enzymatic reaction; regioselective reaction;22.4%
3641-08-5

1,2,4-triazole-3-carboxamide

58-63-9

inosine

36791-04-5

ribavirin

Conditions
ConditionsYield
In water at 60℃; Product distribution; catalyzation by purine nucleoside phosphorylase of Brevibacterium acetylicum ATCC 954, potassium phosphate buffer pH 7.0; reaction time vs. concentrations; with guanosine;
at 60℃; catalyzation by purine nucleoside phosphorylase of Brevibacterium acetylicum ATCC 954, potassium phosphate buffered at pH 7.0; Yield given;
58-63-9

inosine

A

(2R,4aR,6R,7R,7aS)-7-Hydroxy-6-(6-hydroxy-purin-9-yl)-2-thioxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-2-ol anion

B

(2S,4aR,6R,7R,7aS)-7-Hydroxy-6-(6-hydroxy-purin-9-yl)-2-thioxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-2-ol anion

Conditions
ConditionsYield
With potassium hydroxide; trichlorophosphate 1.) trialkyl phosphate, r.t., 1.5 h; 2.) 60 percent CH3CN, 80 deg C; Multistep reaction;
58-63-9

inosine

A

inosine-5'-aldehyde

B

15475-13-5

inosine-5'-carboxylic acid

Conditions
ConditionsYield
With oxygen; nucleoside oxidase In water at 25℃; Product distribution; enzyme activity with further nucleoside bases also tested;
98-88-4

benzoyl chloride

58-63-9

inosine

6741-88-4

2',3',5'-tri-O-benzoylinosine

Conditions
ConditionsYield
With pyridine at 27℃; for 24h; Yield given;
58-63-9

inosine

31766-13-9

9-(2,3-Anhydro-β-D-ribofuranosyl)hypoxanthine

Conditions
ConditionsYield
With Dowex 1 x 2 (OH(-)); acetoxyisobutyryl bromide 1.) MeCN, 19-22 deg C, 3 h, 2.) MeOH, 1 h; Yield given. Multistep reaction;
58-63-9

inosine

42867-68-5

9-(2,3-Dideoxy-β-D-glycero-pent-2-enofuranosyl)hypoxanthine

Conditions
ConditionsYield
Yield given. Multistep reaction;
58-63-9

inosine

A

68-94-0

Allopurinol

B

18646-11-2

α-D-ribofuranosyl-1-phosphate

Conditions
ConditionsYield
With E. coli purine nucleoside phosphorylase Enzyme kinetics; Substitution;
With Phosphate; Cellulomonas sp. purine nucleoside phosphorylase Enzyme kinetics; phosphorolysis;
4074-90-2

divinyl adipate

58-63-9

inosine

Hexanedioic acid (2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester vinyl ester

Conditions
ConditionsYield
With [bmim]BF4; Candida antarctica lipase acrylic resin In acetone at 50℃;88 % Chromat.
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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.