N-α-acetyl-L-glutamine
N-α-acetyl-L-glutamine
CAS: 2490-97-3
Molecular Formula: C7H12N2O4
N-α-acetyl-L-glutamine - Names and Identifiers
| Name | N-α-acetyl-L-glutamine |
| Synonyms | N-ACETYL-L-GLN ACETYL-L-GLUTAMINE N-ACETYL GLUTAMINE N-α-acetyl-L-glutamine N~2~-acetylglutaminato L-GLUTAMINE, N-ACETYL- ACETYL-L-GLUTAMINE, N- N~2~-acetyl-L-glutamine L-GLUTAMINE, N2-ACETYL- N-ALPHA-ACETYL-L-GLUTAMINE n-alpha-acetyl-l-glutamine L-2-ACETAMIDOGLUTARAMIC ACID |
| CAS | 2490-97-3 |
| EINECS | 219-647-7 |
| InChI | InChI=1/C7H12N2O4/c1-4(10)9-5(7(12)13)2-3-6(8)11/h5H,2-3H2,1H3,(H2,8,11)(H,9,10)(H,12,13)/t5-/m0/s1 |
N-α-acetyl-L-glutamine - Physico-chemical Properties
| Molecular Formula | C7H12N2O4 |
| Molar Mass | 188.18 |
| Density | 1.382 g/cm3 |
| Melting Point | 206-208°C |
| Boling Point | 604.9±50.0 °C(Predicted) |
| Specific Rotation(α) | 20D -12.5° (c = 2.9 in water) |
| Flash Point | 319.6°C |
| Water Solubility | almost transparency |
| Vapor Presure | 3.42E-16mmHg at 25°C |
| Appearance | Crystalline |
| Color | White |
| Merck | 14,25 |
| BRN | 1727471 |
| pKa | 3.52±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | -12 ° (C=3, H2O) |
| Physical and Chemical Properties | White crystals. Melting point 195-199 °c. Soluble in water, soluble in ethanol and ethyl acetate. |
| Use | Used as a Biochemical reagent |
N-α-acetyl-L-glutamine - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| TSCA | Yes |
| HS Code | 29241990 |
N-α-acetyl-L-glutamine - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | acetylglutamine is a white crystalline powder; odorless and tasteless. It is dissolved in water and slightly soluble in ethanol. The melting point (Appendix VI C, Part II, Chinese Pharmacopoeia 2000 Edition) is 194-198 ℃. |
| effect | acetylglutamine can improve nerve cell metabolism and maintain good stress function. Reduce blood ammonia. |
| indications | acetylglutamine is mainly used for brain trauma coma, hepatic coma, hemiplegia, high paraplegia, poliomyelitis sequelae, neurotic headache, low back pain, etc. |
| biological activity | Aceglutamide (α-N-Acetyl-L-glutamine, N2-Acetylglutamine) is a class of psychotropic drugs, brain-strengthening drugs, and is a prodrug of glutamine, Has good efficacy and stability. |
| use | medicine. It is used for brain trauma coma, high paraplegia and neurological disorders. It can also treat neurotic headaches, low back pain and sequelae of Japanese encephalitis after poliomyelitis, etc., react with aluminum isopropoxide to obtain aluminum acetylglutamine, and use anti-ulcer drugs. Used as biochemical reagent |
| Production method | L-γ-glutamic acid is obtained by esterification, amination, and acetylation. 1. Esterification Add methanol to a dry reaction tank, and slowly add sulfuric acid under stirring. Cold to below 20 ℃, add L-γ-glutamic acid. After being dissolved, keep the temperature at 20 ℃ for 4h to obtain L-γ-glutamate methyl ester liquid. The weight ratio is L-γ-glutamic acid: methanol: sulfuric acid = 1:10:0.5. 2. Amination The L-γ-glutamic acid methyl ester is liquid cooled to 0 ℃, methyl red is added as indicator, and ammonia is passed to neutral. Add trisulfide carbon to dissolve and continue to pass ammonia to saturation. Place it at 20 ℃ for 4 days to filter, and the filtrate is reduced pressure to remove ammonia. 4N acetic acid was added for neutralization. Keep the temperature at 60 ℃ for 0.5h, and remove carbon trisulfide under reduced pressure. The residual liquid is added with twice the methanol to precipitate. Cooling, filtering, drying, crude. Add water to make 2% aqueous solution, flow through weakly alkaline styrene anion exchange resin 303 × 2(704), collect the effluent, and concentrate under reduced pressure. Add methanol to precipitate, filter, repeatedly wash with methanol and ether, and dry to obtain L-γ-glutamic acid amide. 3. Acetylation Add sodium hydroxide solution (1N) into the reaction tank, cool to 0 ℃, add glutamine under stirring, dissolve and stir for 1h. At the same time, acetic anhydride and sodium hydroxide solution (2N) are added dropwise, and the liquid is placed at 0-5 ℃. Add 6N hydrochloric acid to pH1-2 to precipitate crystallization. Cool, filter, use ice-cold, ionless and not wash to meet the requirements of chlorine, and dry to obtain acetyl glutamine. The weight ratio is L-γ-glutamic acid amide: acetic anhydride (anhydrous) = 1:1.1. The total yield is 50% (for L-γ-glutamic acid). |
Last Update：2024-04-09 20:13:35
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