3-(Allylsulfinyl)-L-alanin
ACSO · rac-Alliin · L-(±)-Alliin · (±)-L-Alliin · (+/-)-L-Alliin · Einecs 241-773-6 · (±)-L-Alliin, ≥90% · (+/-)-L-Alliin[74264]
Identifikatoren & physikalische Daten
| CAS No. | 17795-26-5 |
|---|---|
| Summenformel | C6H11NO3S |
| Durchschnittliche Molmasse | 177,22 g/mol |
| Monoisotopische Masse | 177,04596421 g/mol |
| SMILES | C=CCS(=O)C[C@H](N)C(=O)O |
| InChIKey | XUHLIQGRKRUKPH-ITZCMCNPSA-N |
| PubChem CID | 87310 |
| ChEBI | CHEBI:182413 |
| EC No. | 241-773-6 |
| DTXSID | DTXSID601309766 |
| Lokaler Name | 3-(Allylsulfinyl)-L-alanin |
Chemische & physikalische Eigenschaften
| XLogP | -3,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 99,6 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 181 |
| Collision Cross Section | 134.5 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Siedepunkt | 416.1±45.0 °C(Predicted) |
| Dichte | 1.354±0.06 g/cm3(Predicted) |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | PBS (pH 7.2): 10 mg/ml |
| Aggregatzustand | A crystalline solid |
| pKa (Säurekonstante) | 1.88±0.10(Predicted) |
| Farbe | White to light yellow |
| BRN | 1724805 |
| InChI | 1S/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-,11/m0/s1 |
| InChIKey | XUHLIQGRKRUKPH-ITZCMCNPSA-N |
| SMILES | N[C@@H](CS(=O)CC=C)C(O)=O |
Sicherheit & Vorschriften
| Wassergefährdungsklasse (WGK) | 3 |
|---|---|
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Beschreibung
Alliin is a cysteine sulfoxide constituent of garlic that is converted by alliinase to allicin, which imparts its pungent aroma and flavor. Alliin exhibits anti-cancer, anti-microbial, anti-hypertensive, cardioprotective, and anti-oxidant activities. It has been shown to inhibit squalene monooxygenase, a rate-limiting step in the downstream pathway of cholesterol biosynthesis, with an IC50 value of 120 μM.
Verwenden
rac-Alliin has shown notable preventive effects on cardiac marker enzymes and lipids in isoproterenol-induced myocardial injury. rac-Alliin is also known to exhibit anticancer, antimicrobial, antihypertensive, antioxidant activities.