Inosine supplier | CasNO.58-63-9

Name
Inosine
EINECS 200-390-4
CAS No. 58-63-9
Article Data92
CAS DataBase
Density 2.085 g/cm³
Solubility 2.1 g/100 mL (20 °C) in water
Melting Point 222-226 °C (dec.)(lit.)
Formula C₁₀H₁₂N₄O₅
Boiling Point 732.815 °C at 760 mmHg
Molecular Weight 268.229
Flash Point 396.993 °C
Transport Information
Appearance White crystalline powder
Safety 24/25-36-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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;
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

Conditions	Yield
Multistep reaction;

: 58-61-7
adenosine

: 58-63-9
inosine

Conditions

Conditions	Yield
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;

: 131-99-7, 21138-48-7, 21214-07-3, 54656-49-4, 56553-00-5
inosine-5'-monophosphate

: 58-63-9
inosine

Conditions

Conditions	Yield
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

Conditions	Yield
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

: 118-00-3
G

: 58-63-9
inosine

Conditions

Conditions	Yield
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

Conditions	Yield
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

: 146469-96-7, 98325-49-6, 98325-50-9
hypoxanthine

: 99790-49-5
α-D-ribose-1-phosphate

: 58-63-9
inosine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With dmap; triethylamine In acetonitrile at 20℃;	100%
With pyridine at 0℃; for 16h;
With dmap; triethylamine In acetonitrile for 1h;

: 3083-77-0
araU

: 58-63-9
inosine

: 7013-16-3
9-(β-D-arabinofuranosyl)-9H-purin-6(1H)-one

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With p-toluenesulfonic acid monohydrate; acetic anhydride In acetonitrile	47%

: 58-63-9
inosine

: 870-63-3
prenyl bromide

: 1237496-78-4
6-(3-methyl-2-butenyloxy)-9-(β-D-ribofuranosyl)purine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With pyridine at 27℃; for 24h; Yield given;

: 58-63-9
inosine

: 31766-13-9
9-(2,3-Anhydro-β-D-ribofuranosyl)hypoxanthine

Conditions

Conditions	Yield
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

Conditions	Yield
Yield given. Multistep reaction;

: 58-63-9
inosine

A: 68-94-0
Allopurinol

B: 18646-11-2
α-D-ribofuranosyl-1-phosphate

Conditions

Conditions	Yield
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

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

Inosine Consensus Reports

Reported in EPA TSCA Inventory.

Inosine 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)	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.

Product Name

Inosine

Synthetic route

Inosine Consensus Reports

Inosine Specification

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