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INOSINE CAS 58-63-9
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58-63-9 Usage

Purification Methods

(-)-Inosine forms anhydrous crystals from aqueous 80% EtOH but the dihydrate from H2O. [Beilstein 31 H 25, 26 III/IV 2087.]

Chemical Properties

White crystalline powder

Uses

Has neuroprotective properties improving axonal wiring. Has been used to treat stroke patients to restore neural function.

Definition

ChEBI: A purine nucleoside in which hypoxanthine is attached to ribofuranose via a beta-N9-glycosidic bond.

Uses

cell function activator, cardiotonic
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

58-63-9 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A14459)  Inosine, 98+%    58-63-9 100g 2025.0CNY Detail
Alfa Aesar (A14459)  Inosine, 98+%    58-63-9 25g 628.0CNY Detail
Alfa Aesar (A14459)  Inosine, 98+%    58-63-9 5g 219.0CNY Detail
TCI America (I0037)  Inosine  >98.0%(HPLC)(T) 58-63-9 500g 4,500.00CNY Detail
TCI America (I0037)  Inosine  >98.0%(HPLC)(T) 58-63-9 25g 530.00CNY Detail

58-63-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Inosine

1.2 Other means of identification

Product number -
Other names 6-Oxopurine riboside

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:58-63-9 SDS

58-63-9Synthetic 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

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

inosine
58-63-9

inosine

B

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
Multistep reaction;
adenosine
58-61-7

adenosine

inosine
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;
uridine
58-96-8

uridine

inosine
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
α-D-ribose-1-phosphate
99790-49-5

α-D-ribose-1-phosphate

inosine
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
α-D-ribose-1-phosphate
99790-49-5

α-D-ribose-1-phosphate

inosine
58-63-9

inosine

Conditions
ConditionsYield
In aq. phosphate buffer at 20℃; pH=7.5;
α-D-ribofuranose-1-O-phosphate barium salt

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

6-hydroxypurine
68-94-0

6-hydroxypurine

inosine
58-63-9

inosine

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

6-hydroxypurine

uridine
58-96-8

uridine

inosine
58-63-9

inosine

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

Allopurinol

uridine
58-96-8

uridine

inosine
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;
acetic anhydride
108-24-7

acetic anhydride

inosine
58-63-9

inosine

2’,3’,5’-tri-O-acetylinosine
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;
inosine
58-63-9

inosine

9-(β-D-arabinofuranosyl)-9H-purin-6(1H)-one
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%
Acetanilid
103-84-4

Acetanilid

inosine
58-63-9

inosine

1,2,3,5-tetraacetylribose
13035-61-5

1,2,3,5-tetraacetylribose

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

inosine

tert-butylchlorodiphenylsilane
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

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%
inosine
58-63-9

inosine

C10H10(2)H2N4O5
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%
vinyl acetate
108-05-4

vinyl acetate

inosine
58-63-9

inosine

5'-O-acetylinosine
28526-32-1

5'-O-acetylinosine

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

dipentyl ketone

inosine
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

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%
propan-2-one O-butyryl oxime
133360-56-2

propan-2-one O-butyryl oxime

inosine
58-63-9

inosine

Butyric acid (2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester
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%
vinyl acetate
108-05-4

vinyl acetate

inosine
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

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

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
acetone oxime acrylate
145355-61-9

acetone oxime acrylate

inosine
58-63-9

inosine

Acrylic acid (2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester
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%
thymin
65-71-4

thymin

inosine
58-63-9

inosine

5-Methyluridine
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%
4-heptanone
123-19-3

4-heptanone

inosine
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

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%
cis-dichloro(DL-ethionine)platinum(II)
21434-62-8, 41475-72-3

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

inosine
58-63-9

inosine

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

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%
inosine
58-63-9

inosine

α-D-ribose-1-phosphate
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;
2-acetoxyethyl acetoxymethyl ether
59278-00-1

2-acetoxyethyl acetoxymethyl ether

inosine
58-63-9

inosine

9-((2-acetoxyethoxy)methyl)-hypoxanthine
150581-50-3

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

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

inosine

prenyl bromide
870-63-3

prenyl bromide

6-(3-methyl-2-butenyloxy)-9-(β-D-ribofuranosyl)purine
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;
inosine
58-63-9

inosine

9-(2-O-Triflyl-β-L-ribofuranosyl)hypoxanthine
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%
inosine
58-63-9

inosine

LACTOSE
5965-66-2

LACTOSE

C16H22N4O10

C16H22N4O10

Conditions
ConditionsYield
With β-galactosidase from Bacillus megaterium YZ08 In dimethyl sulfoxide at 35℃; Solvent; Enzymatic reaction; regioselective reaction;22.4%
1,2,4-triazole-3-carboxamide
3641-08-5

1,2,4-triazole-3-carboxamide

inosine
58-63-9

inosine

ribavirin
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;
inosine
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

(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

(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;
inosine
58-63-9

inosine

A

inosine-5'-aldehyde

inosine-5'-aldehyde

B

inosine-5'-carboxylic acid
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;
benzoyl chloride
98-88-4

benzoyl chloride

inosine
58-63-9

inosine

2',3',5'-tri-O-benzoylinosine
6741-88-4

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

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

inosine

9-(2,3-Anhydro-β-D-ribofuranosyl)hypoxanthine
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;
inosine
58-63-9

inosine

9-(2,3-Dideoxy-β-D-glycero-pent-2-enofuranosyl)hypoxanthine
42867-68-5

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

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

inosine

A

Allopurinol
68-94-0

Allopurinol

B

α-D-ribofuranosyl-1-phosphate
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;
divinyl adipate
4074-90-2

divinyl adipate

inosine
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

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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