Levoglutamid
GLUTAMINE · GLN · H-GLN-OH · L-GLN · L-Glutamin · L-Gln-OH · FEMA 3684 · H-L-GLN-OH
Identifikatoren & physikalische Daten
| CAS No. | 56-85-9 |
|---|---|
| Summenformel | C5H10N2O3 |
| Durchschnittliche Molmasse | 146,14 g/mol |
| Monoisotopische Masse | 146,06914219 g/mol |
| SMILES | NC(=O)CC[C@H]([NH3+])C(=O)[O-] |
| InChIKey | ZDXPYRJPNDTMRX-VKHMYHEASA-N |
| PubChem CID | 6992086 |
| ChEBI | CHEBI:58359 |
| Lokaler Name | Levoglutamid |
Chemische & physikalische Eigenschaften
| XLogP | -2,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 111 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 140 |
| LogP (Verteilungskoeffizient) | -3.64 |
| Löslichkeit | 41.3 mg/mLH2O: 25 mg/mLSoluble in water, dimethyl sulfoxide and ethanol. Insoluble in methanol, ether, benzene, acetone, ethyl acetate and chloroform. |
| Schmelzpunkt | 185 °Cdecomposes around 185°C |
| Physical Description | Solid |
| Dissociation Constants | 2.17 |
| Siedepunkt | 265.74°C (rough estimate) |
| Dichte | 1.47 g/cm 3 at 20 °C |
| Brechungsindex | 6.8 ° (C=4, H2O) |
| FEMA | 3684 | L-GLUTAMINE |
| Flammpunkt | Not applicable |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | 2.17(at 25℃) |
| Aggregatzustand | powder to crystal |
| Farbe | White |
| pH | 5.0-6.0 (25℃, 0.1M in H2O) |
| Geruch | at 100.00 %. very mild milky custard cocoa oily |
| Geruchsart | milky |
| Biologische Quelle | synthetic |
| Decomposition | 185 ºC |
| Merck | 14,4471 |
| JECFA Number | 1430 |
| BRN | 1723797 |
| Henry-Konstante | 3.3×1010 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Moisture and light sensitive. Incompatible with moisture, strong oxidizing agents. |
| Hauptanwendungen | agriculture |
| Kosmetik-Inhaltsstoffe Funktionen | HAIR CONDITIONINGSKIN CONDITIONINGANTISTATIC |
| InChI | 1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1 |
| InChIKey | ZDXPYRJPNDTMRX-VKHMYHEASA-N |
| SMILES | N[C@@H](CCC(N)=O)C(O)=O |
| LogP (Verteilungskoeffizient) | -1.67 |
| CAS Datenbank | 56-85-9(CAS DataBase Reference) |
| NIST chemische Informationen | L-Glutamine(56-85-9) |
| EPA chemische Informationen | L-Glutamine (56-85-9) |
Sicherheit & Vorschriften
| Wassergefährdungsklasse (WGK) | 2 |
|---|---|
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29241900 |
| RTECS-Nr. | MA2275100 |
| R-Sätze (R) | 36-36/37/38 |
| Toxizität | LD50 orally in Rabbit: 7500 mg/kg |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-24/25-36/37/39-27 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 56-85-9(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Glutamine (abbreviated as Gln or Q) is one of the 20 amino acids encoded by the standard genetic code. It is not recognized as an essential amino acid, but may become conditionally essential in certain situations, including intensive athletic training or certain gastrointestinal disorders.Its side-chain is an amide formed by replacing the side-chain hydroxyl of glutamic acid with an amine functional group, making it the amide of glutamic acid. Its codons are CAA and CAG. In human blood, glutamine is the most abundant free amino acid, with a concentration of about 500–900 μmol / l .
Occurrence
Occurrences in natureGlutamine is the most abundant naturally occurring, nonessential amino acid in the human body, and one of the few amino acids that can directly cross the blood-brain barrier.In the body, it is found circulating in the blood, as well as stored in the skeletal muscles. It becomes conditionally essential (requiring intake from food or supplements) in states of illness or injury.Dietary sourcesDietary sources of L-glutamine include beef, chicken, fish, eggs, milk, dairy products, wheat, cabbage, beets, beans, spinach, and parsley. Small amounts of free L-glutamine are also found in vegetable juices.Aiding gastrointestinal functionGlutamine-enriched diets have been linked with maintenance of gut barrier function and cell differentiation, suggesting glutamine may help to protect the lining of the gastrointestinal tract or mucosa. People who have inflammatory bowel disease (ulcerative colitis and Crohn' s disease) may not have enough glutamine, but two clinical trials found taking glutamine supplements did not improve symptoms of Crohn' s disease.
Verwenden
L-Glutamine is an essential amino acid that is a crucial component of culture media that serves as a major energy source for cells in culture. L-Glutamine is very stable as a dry powder and as a frozen solution. In liquid media or stock solutions, however, L-glutamine degrades relatively rapidly. Optimal cell performance usually requires supplementation of the media with L-glutamine prior to use.
Herstellung & Synthese
synthetische
By isolation from sugar beet juice.