L-Prolin
PRO · H-PRO-OH · L-PRO · l-prolin · L-Pro-OH · 2-pyrrolidinecarboxylic acid · (S)-PYRROLIDINE-2-CARBOXYLIC ACID · (2S)-pyrrolidine-2-carboxylic acid
Identifikatoren & physikalische Daten
| CAS No. | 147-85-3 |
|---|---|
| Summenformel | C5H9NO2 |
| Durchschnittliche Molmasse | 115,13 g/mol |
| Monoisotopische Masse | 115,06332853 g/mol |
| SMILES | O=C(O)C1CCCN1 |
| InChIKey | ONIBWKKTOPOVIA-UHFFFAOYSA-N |
| PubChem CID | 614 |
| ChEBI | CHEBI:26271 |
| EC No. | 210-189-3 |
| DTXSID | DTXSID9041104 |
| Lokaler Name | L-Prolin |
Chemische & physikalische Eigenschaften
| XLogP | -2,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 49,3 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 103 |
| Stoffklassen | Biological Agents -> Amino Acids and Derivatives |
| Arzneimittel | Pharmaceuticals |
| Physical Description | Beige solid[Sigma-Aldrich MSDS] |
| Schmelzpunkt | 228 °C (dec.) (lit.) |
| Siedepunkt | 215.41°C (rough estimate) |
| Dichte | 1.35 |
| Dampfdruck | 0Pa at 25℃ |
| FEMA | 3319 | L-PROLINE |
| Brechungsindex | -85 ° (C=4, H2O) |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | H2O: 50 mg/mLsoluble |
| Aggregatzustand | powder |
| pKa (Säurekonstante) | 1.95, 10.64(at 25℃) |
| Farbe | White |
| pH | 6.0-7.0 (25℃, 1M in H2O) |
| Geruch | at 100.00 %. odorless |
| Geruchsart | odorless |
| Biologische Quelle | synthetic |
| JECFA Number | 1425 |
| Merck | 14,7780 |
| BRN | 80810 |
| Stabilität | Stable. Incompatible with strong oxidizing agents. |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONINGHAIR CONDITIONING |
| InChI | 1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1 |
| InChIKey | ONIBWKKTOPOVIA-UHFFFAOYSA-N |
| SMILES | OC(=O)[C@@H]1CCCN1 |
| LogP (Verteilungskoeffizient) | -2.54 at 20℃ |
| CAS Datenbank | 147-85-3(CAS DataBase Reference) |
| NIST chemische Informationen | Proline(147-85-3) |
| EPA chemische Informationen | L-Proline (147-85-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 95.5% (21 of 22) of all reports.Not ClassifiedAggregated GHS information provided per 22 reports by companies from 2 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: DL-Proline |
| Weitere Sicherheitsinformationen | IMAP assessments - DL-Proline: Environment tier I assessment |
| Gefahrenübersicht | May cause irritation[Sigma-Aldrich MSDS] |
| Hazard Classes and Categories | Not Classified |
| F | 3-10 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29339990 |
| RTECS-Nr. | TW3584000 |
| R-Sätze (R) | 36/37/38-22 |
| Toxizität | LD50 orally in Rabbit: > 5110 mg/kg |
| Gefahrensymbole | Xi,Xn |
| Sicherheitshinweise (S) | 24/25-36/37/39-26 |
| Lagerklasse | 13 - Non Combustible Solids |
| Gefahrstoffdaten | 147-85-3(Hazardous Substances Data) |
Anwendungen & Verwendung
Occurrence
Reported found as a component in many proteins; also widely occurring as the free acid in natural products. A major constituent of collagen, the main fibrous protein found in bone, cartilage and other connective tissue.
Verwenden
L-Proline is an amino acid and precursor (with vitamin C) for collagen, the building block of the structure of tendons, ligaments, arteries, veins and muscles. It is important in wound healing.
Herstellung & Synthese
synthetische
Synthesis of L-proline: Using glutamic acid as a raw material, it is esterified with absolute ethanol under the catalysis of sulfuric acid, and triethanolamine is added to free the aminosulfate to obtain glutamic acid-δ-ethyl ester. The glutamic acid-δ-ethyl ester is then reduced with a metal reducing agent potassium borohydride to obtain crude proline, which is finally separated and purified to obtain crude L-proline.