Inosine CAS 58-63-9
Introduction：Basic information about Inosine CAS 58-63-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Inosine Basic information
| Product Name: | Inosine |
| Synonyms: | Atorel;beta-D-Ribofuranoside, hypoxanthine-9;beta-Inosine;HXR;Hypoxanthine D-riboside;Hypoxanthine, 9-beta-D-ribofuranosyl-;hypoxanthined-riboside;hypoxanthinenucleoside |
| CAS: | 58-63-9 |
| MF: | C10H12N4O5 |
| MW: | 268.23 |
| EINECS: | 200-390-4 |
| Product Categories: | Furans;Nucleic acids;Bases & Related Reagents;Nucleotides;Nucleotides and Nucleosides;Antivirals for Research and Experimental Use;Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Inhibitors;58-63-9;Elisa Kit-Mouse Elisa Kit;Nucleosides-Ribonucleosides |
| Mol File: | 58-63-9.mol |
Inosine Chemical Properties
| Melting point | 222-226 °C (dec.) (lit.) |
| alpha | -49.2 º (c=1,H2O 18 ºC) |
| Boiling point | 226 C (dec.) |
| density | 1.3846 (rough estimate) |
| refractive index | -52 ° (C=1, H2O) |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| solubility | H2O: 0.5 M, clear, colorless |
| pka | 13.24±0.70(Predicted) |
| form | Crystalline Powder |
| color | White |
| Odor | Odorless |
| PH | 1.2；8.8 |
| Optical Rotation | Consistent with structure |
| Water Solubility | 2.1 g/100 mL (20 ºC) |
| λmax | 251 (pH 0)；248.5 (pH 6)；253 (pH 11) |
| Merck | 14,4975 |
| BRN | 624889 |
| Stability: | Hygroscopic |
| Cosmetics Ingredients Functions | SKIN PROTECTING SKIN CONDITIONING |
| InChI | 1S/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 |
| InChIKey | UGQMRVRMYYASKQ-PKJMTWSGSA-N |
| SMILES | OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3C(=O)NC=Nc23 |
| LogP | -1.970 (est) |
| CAS DataBase Reference | 58-63-9(CAS DataBase Reference) |
| NIST Chemistry Reference | Inosine(58-63-9) |
| EPA Substance Registry System | Inosine (58-63-9) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 24/25-36-26 |
| WGK Germany | 2 |
| RTECS | NM7460000 |
| F | 10 |
| TSCA | TSCA listed |
| HS Code | 29389090 |
| Storage Class | 11 - Combustible Solids |
| Toxicity | LD50 oral in rat: > 10gm/kg |
| Chemical Properties | White crystalline powder |
| Originator | Foreart,Guarnieri,Italy,1970 |
| Occurrence | Inosine is a synthetic |
| Uses | Has neuroprotective properties improving axonal wiring. Has been used to treat stroke patients to restore neural function. |
| Uses | cell function activator, cardiotonic |
| Uses | Suppresses the increase of glucose and insulin in the blood |
| Uses | Inosine has been used:
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| Definition | ChEBI: A purine nucleoside in which hypoxanthine is attached to ribofuranose via a beta-N9-glycosidic bond. |
| Manufacturing Process | As described in US Patent 3,049,536, inosine may be prepared starting withadenosine. The Deamination of Adenosine: 20 g of adenosine are dissolved in one liter ofwater by warming, and after cooling to room temperature 120 g of bariumnitrite (monohydrate) are added to the solution. Under stirring there is addedin time intervals of one hour 160 cc of 2 N sulfuric acid after each timeinterval. After the third addition, the reaction mass is allowed to stand for 3hours at room temperature. The solution is then tested for barium, and ifsome barium is still present a slight excess of sulfuric acid is added. 300 cc ofmethanol is then added. In order to drive off the excess of nitrous acid, CO2 isconducted through the solution until the solution is free of nitrous acid asdetermined by testing with potassium iodide-starch paper. The precipitatedbarium sulfate is separated by centrifugation. The residue is washed one timewith about 500 cc of water. The total volume of the centrifugate is about 2.3liters. Isolation of Inosine by Ion Exchange Method: Half of the above clearcentrifugate (1.15 liters) is treated with 250 cc of anion exchange(bicarbonate form) and stirred together therewith for 16 hours at roomtemperature. The pH value is increased thereby to about 4 to 5. The ionexchanger is filtered off under suction and washed 3 times, each time with150 cc of water. The solution is brought to a pH value of 7 by means ofnormal sodium hydroxide (total volume of the solution about 1.55 liters), andconcentrated to a volume of about 100 cc under vacuum. The inosine is crystallized overnight in an ice box and the inosine is thenfiltered off by suction, washed with a small amount of ice water and dried at atemperature of 105°C. A first fraction of crude inosine consisting of 5.4 ghaving a purity of 99% is obtained. Further fractions of crude inosine areobtained from the mother liquid by concentration, the total amountconstituting 3.2 g having a purity of 96 to 98%. The yield of crude inosine is8.6 g which is equal to 86%. Recrystallization of the Crude Inosine: 17.0 g of crude inosine are dissolved in400 cc of 80% ethanol in a water bath, filtered while hot and brought tocrystallization in an ice box. After standing overnight the crystalline material isfiltered off under suction and washed with ice water. The pure inosine is driedin a drying chamber at a temperature of 105°C. The yield of pure inosine is15.0 g which is equal to 75%. The yield can be further increased by workingup the mother liquor of the crystallization as set forth above. Alternatively, inosine may be made by fermentation as described in US Patent3,111,459. 3 ml portions of a culture medium consisting of glucose (5 g/dl),ammonium chloride (0.4 g/dl), urea (0.4 g/dl), KH2PO4 (0.1 g/dl), MgSO4 ·7H2O (0.02 g/dl), Mn++ (2 ppm), Fe++ (2ppm), casein hydrolyzate (0.2 g/dl),yeast extract (0.2 g/dl), corn steep liquor (0.2 ml/dl), polypeptone (0.1 g/dl),meat extract (0.1 g/dl) and sodium ribonucleate (10 mg/dl) were poured intorespective test tubes and each tube was sterilized at 115°C for 10 minutes.Thereafter separately sterilized calcium carbonate was added in the amount of2 g/dl and then cells of Bacillus subtilis S26910 were inoculated into theabove media and cultured with shaking at 30°C for 20 hours. The resulting culture liquids were utilized for seeding, 20 ml of the mediumhaving the composition described above were poured into a 500 ml shakingflask and sterilized at 115°C for 10 minutes and five drops of the above seedwere added, and then cultured with shaking at 30°C for 65 hours. Thereafter0.15 g/dl of inosine were accumulated. The inosine-containing solution, which was obtained by separating the cellsfrom the resulting fermentation liquid, was treated with both decolorizingresins and anion exchange resins by means of a conventional method andthen acetone was added to crystallize the inosine. 1.47 g of the crude crystalsof inosine were obtained from 3.5 liters of the culture liquid containing 1 g ofinosine per liter. |
| Therapeutic Function | Cardiotonic |
| General Description | Inosine is a non-canonical nucleotide majorly present as monophosphate. It has ability to base pair with deoxythymidine, deoxyadenosine and deoxyguanosine. Incorporation of inosine in place of guanine modulates translational events. Inosine has antioxidant, anti-inflammatory and neuroprotective functionality. Inosine is prescribed as a therapeutic supplement for nerve injury, inflammation and oxidative stress. It modulates biological processes through adenosine receptors. Its enhances neurite outgrowth in depressive disorders via adenosine receptors. Inosine is also used for treating sepsis in infections. |
| Biochem/physiol Actions | Inosine is a potent stimulator of nerve growth factor (NGF) induced neurite outgrowth. The elevated levels of inosine in brain following injury are associated with the increased expression proteins related to axonal regeneration and growth. Mice given inosine demonstrated enhanced recovery of fine motor control following ischemic brain damage. Inosine may be used in studies of the process A-to-I RNA editing. |
| target | NF-kB | SOD | PKA | AChR | PKC | Calcium Channel |
| Purification Methods | (-)-Inosine forms anhydrous crystals from aqueous 80% EtOH but the dihydrate from H2O. [Beilstein 31 H 25, 26 III/IV 2087.] |
Inosine Preparation Products And Raw materials
| Raw materials | Sodium chloride-->Disodium 5'-Inosinate-->Platinum-->Agar-->TRIS BORATE EDTA BUFFER, 10X, DNASE, RNASE AND PROTEASE FREE, PH 8.3, FOR MOLECULAR BIOLOGY-->Guanosine 5'-monophosphate disodium salt-->Inosinic Acid-->BEEF EXTRACT-->Sulfuric acid-->Adenosine-->BARIUM NITRITE |
| Preparation Products | DL-Tryptophan-->Ribavirin-->Calcium 5'-ribonucleotide-->Dideoxyinosine-->beta-D-Ribofuranose 1,2,3,5-tetraacetate-->2-(6-ethylaminopurin-9-yl)-5-(hydroxymethyl)oxol-->5''-O-(4,4''-Dimethoxytrityl)-inosine-->6-Chloropurine ribonucleoside-->N6-CYCLOHEXYLADENOSINE |
