Glutaminsure
GLU · H-GLU-OH · L-GLU · glutamic · L-Glutamate · L-Glu-OH · (S)-GLUTAMIC ACID · FEMA 3285
Identifikatoren & physikalische Daten
| CAS No. | 56-86-0 |
|---|---|
| Summenformel | C5H9NO4 |
| Durchschnittliche Molmasse | 147,13 g/mol |
| Monoisotopische Masse | 147,05315777 g/mol |
| SMILES | NC(CCC(=O)O)C(=O)O |
| InChIKey | WHUUTDBJXJRKMK-UHFFFAOYSA-N |
| PubChem CID | 611 |
| ChEBI | CHEBI:18237 |
| DTXSID | DTXSID0046987 |
| Lokaler Name | Glutaminsure |
Chemische & physikalische Eigenschaften
| XLogP | -3,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 101 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 145 |
| Stoffklassen | Biological Agents -> Amino Acids and Derivatives |
| Arzneimittel | Pharmaceuticals |
| Dampfdruck | 0.00000052 [mmHg] |
| Physical Description | Solid[Merck Index] |
| Schmelzpunkt | 205 °C (dec.) (lit.) |
| Siedepunkt | 267.21°C (rough estimate) |
| Dichte | 1.54 g/cm3 at 20 °C |
| Brechungsindex | 1.4300 (estimate) |
| FEMA | 3285 | L-GLUTAMIC ACID |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | 1 M HCl: 100 mg/mL7.5 g/L (20 ºC) |
| Aggregatzustand | powder |
| pKa (Säurekonstante) | 2.13(at 25℃) |
| Farbe | White |
| pH | 3.0-3.5 (8.6g/l, H2O, 25℃) |
| Geruch | at 100.00 %. mild yeast baked bread |
| Geruchsart | yeasty |
| Biologische Quelle | non-animal source |
| Merck | 14,4469 |
| JECFA Number | 1420 |
| BRN | 1723801 |
| Hauptanwendungen | pharmaceutical (small molecule) |
| Kosmetik-Inhaltsstoffe Funktionen | HAIR CONDITIONINGANTISTATICHUMECTANT |
| InChI | 1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1 |
| InChIKey | WHUUTDBJXJRKMK-VKHMYHEASA-N |
| SMILES | N[C@@H](CCC(O)=O)C(O)=O |
| LogP (Verteilungskoeffizient) | -3.69 |
| CAS Datenbank | 56-86-0(CAS DataBase Reference) |
| NIST chemische Informationen | L-Glutamic acid(56-86-0) |
| EPA chemische Informationen | L-Glutamic acid (56-86-0) |
Sicherheit & Vorschriften
| Regulatorische Informationen | Chemical: DL-Glutamic acid |
|---|---|
| Weitere Sicherheitsinformationen | IMAP assessments - DL-Glutamic acid: Environment tier I assessment |
| Gefahrenübersicht | Human ingestion of 71 mg/kg causes headache[RTECS] May cause irritation[Sigma-Aldrich MSDS] See Glutamic acid. |
| F | 10 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29224200 |
| RTECS-Nr. | LZ9700000 |
| R-Sätze (R) | 36/37/38 |
| Toxizität | LD50 orally in Rabbit: > 30000 mg/kg |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 24/25-36-26 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 56-86-0(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
L-Glutamic acid, or L-2-aminopentanedioic acid, is a naturally occurring amino acid of plant and animal proteins. It has a very faint odor reminiscent of yeast or freshly baked bread. It has a mild, somewhat sweet, meat-like taste.The average glutamic acid content of food proteins is 20 percent. Expressed as glutamic acid per 100 g of the edible portions, medium fat beef contains about 2.65 g of glutamic acid; whole liquid cow milk, 0.82 g; lean pork, 2.16 g; haddock, 2.32 g; peas, 5.58 g; soybeans, 7.01 g; commeal, 1.62 g; and whole grain wheat flour, 4.16 g. In addition, free glutamic acid is present in many vegetables, fish, and meats in small amounts (0. 005 to 0.23 g per 100 g) and as high as 2 g per 100 g in some varieties of cheese. Recent estimates of free amino acids in the milk of various species indicated that the free glutamic acid in human milk is about 0.22 g per 100 mL.Glutamic acid and its salts are prepared commercially by hydrolysis of gluten (wheat, corn, soybean, sugarbeet protein); by fermentation from glucose-containing raw materials; the racemic acid may be resolved into the d- and ι-isomer by fractional crystallization; from 2 -cyclopentenylamine; by microbial conversion of aketoglutaric acid; or by an alternative method, using Bacillus megatherium-cereus; from fumaric acid using B. pumilus; from starch.Glutamic acid and the hydrochloride as well as the mono-sodium, -potassium, and -ammonium salts of L-glutamic acid share similar physical properties: they are nearly odorless, white, free-flowing crystalline powders, and except for glutamic acid and glutamic acid hydrochloride, are freely soluble in water. Glutamic acid is slightly soluble and glutamic acid hydrochloride moderately soluble in water. The pH of a saturated solution is about 3.2.
Occurrence
Reported as occurring in many vegetable proteins, in beef fbrin, in the chrysalis of silkworm, in the hydro- lysate of crystalline insulin Also present in other important peptides, such as glutathione, tyrocidin, folic acid, β-lactoglobulin, secretin and bacitracin, and in growth hormone
Verwenden
L-glutamic acid or its salt, monosodium glutamate (MSG), is used as an additive to human food to enhance the taste. Although seaweed had been used in Asia to enhance food flavor for over 1000 years, it was not until 1908 that the essential component responsible for the flavor phenomenon was identified as glutamic acid. From 1910 until 1956, monosodium glutamate was extracted from sea weed, a slow and costly method. In 1956, Ajinomoto, a Japanese company, succeeded in producing glutamic acid by means of fermentation. Today, L-glutamic acid or MSG is generally made by microbial fermentation using genetically modified bacteria.
Herstellung & Synthese
synthetische
By hydrolysis of gluten (wheat, corn or other vegetable sources); by fermentation from glucose-containing raw materials; the racemic acid may be resolved into the d- and l-isomer by fractional crystallization; from 2-cyclopentenylamine; by microbial conversion of α-ketoglutaric acid; or by an alternative method, using Bacillus megatherium-cereus; from fumaric acid, using B pumilus; from starch.