S-Allylacrylo-1-sulfinothioat
Allitrid · garlic meal · ALLICIN · AlliMed · alliosan · C6H10S2O · Allisatin · ARICINE(P)
Identifikatoren & physikalische Daten
| CAS No. | 539-86-6 |
|---|---|
| Summenformel | C6H10OS2 |
| Durchschnittliche Molmasse | 162,3 g/mol |
| Monoisotopische Masse | 162,01730729 g/mol |
| SMILES | C=CCSS(=O)CC=C |
| InChIKey | JDLKFOPOAOFWQN-UHFFFAOYSA-N |
| PubChem CID | 65036 |
| ChEMBL | CHEMBL359965 |
| ChEBI | CHEBI:28411 |
| EC No. | 208-727-7 |
| DTXSID | DTXSID6043707 |
| Lokaler Name | S-Allylacrylo-1-sulfinothioat |
Chemische & physikalische Eigenschaften
| XLogP | 1,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 61,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 120 |
| Löslichkeit | 24 mg/mL at 10 °CDMSO : 5 mg/mL (30.81 mMNeed ultrasonic)H2O : < 0.1 mg/mL (insoluble)24g/L(10 ºC) |
| Schmelzpunkt | 25 °C25°C |
| Physical Description | Solid |
| Siedepunkt | 259°C (rough estimate) |
| Dichte | d420 1.112 |
| Brechungsindex | nD20 1.561 |
| Lagerbedingungen | 4°C, away from moisture and light |
| Aggregatzustand | liquid |
| Farbe | Colorless to light yellow |
| InChI | InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2 |
| InChIKey | JDLKFOPOAOFWQN-UHFFFAOYSA-N |
| SMILES | C(S(SCC=C)=O)C=C |
| LogP (Verteilungskoeffizient) | 1.133 (est) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (100%)Eye Irrit. 2 (100%)STOT SE 3 (100%) |
| Zollcode | 29329990 |
| Toxizität | LD50 in mice (mg/kg): 60 i.v.120 s.c. (Cavallito, Bailey) |
Anwendungen & Verwendung
Beschreibung
Allicin is one of the major allergens in garlic (Allium sativum L.). It is responsible of the characteristical fiavour of the bulbs.
History
As the main active substance of garlic, garlic was separated by Cavallito and Bailey in 1944 from crushed garlic. Cavallito firstly clarified the physical properties and chemical structure of the scent of garlic.Fresh garlic does not contain free allicin but only its precursor material alliin. When the garlic undergoes physical mechanical crushing, garlic alliinase is activated and catalyzes the breakdown of alliin into allicin.The reported preparation methods of allicin contain extraction, biosynthesis, and chemical synthesis. Chemical synthesis starts from raw material of diallyldisulfides, m-chloroperoxy benzoic acid to get crude allicin. According to the United States patent report, biosynthesis preparation of allicin comes from natural sources or synthetic, after it is made into a certain concentration of aqueous solution, it is converted into allicin by reaction with alliinase. Extraction of allicin with low boiling nonpolar solvent can acquire pure allicin, but it must be stored at 70°C to prevent from decomposing.
Verwenden
Allicin is naturally formed by the action of the enzyme allicinase on alliin when the tissue of the garlic bulb is disrupted. Allicin shows antibacterial activity.