beta-D-Galactopyranosid, (3 beta,5 alpha, 22 beta, 25S)-spirosolan-3-yl-O-beta-D-glucopyranosyl-(1=> 2)-O-(beta-D-xylopyranosyl-(1=> 3))-O-beta-D-glucopyranosyl-(1=> 4)-
alpha-tomatine · TOMATIN · Tomatine [for Cholesterol assay] · omatine · Tomatie · TOMATINE · NSC 9223 · a-Tomatine
Identifikatoren & physikalische Daten
| CAS No. | 17406-45-0 |
|---|---|
| Summenformel | C50H83NO21 |
| Durchschnittliche Molmasse | 1.034,2 g/mol |
| Monoisotopische Masse | 1.033,54575866 g/mol |
| SMILES | CC1CCC2(NC1)OC1CC3C4CCC5CC(OC6OC(CO)C(OC7OC(CO)C(O)C(OC8OCC(O)C(O)C8O)C7OC7OC(CO)C(O)C(O)C7O)C(O)C6O)CCC5(C)C4CCC3(C)C1C2C |
| InChIKey | REJLGAUYTKNVJM-UHFFFAOYSA-N |
| PubChem CID | 5513 |
| Lokaler Name | beta-D-Galactopyranosid, (3 beta,5 alpha, 22 beta, 25S)-spirosolan-3-yl-O-beta-D-glucopyranosyl-(1=> 2)-O-(beta-D-xylopyranosyl-(1=> 3))-O-beta-D-glucopyranosyl-(1=> 4)- |
Chemische & physikalische Eigenschaften
| XLogP | -0,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 338 |
| H-Brücken-Donoren | 13 |
| H-Brücken-Akzeptoren | 22 |
| Frei drehbare Bindungen | 11 |
| Schwere Atome | 72 |
| Formalladung | 0 |
| Komplexität | 1.840 |
| Schmelzpunkt | 263 - 267 °C300-305°C |
| Physical Description | Solid |
| Siedepunkt | 806.69°C (rough estimate) |
| Dichte | 1.48±0.1 g/cm3 (20 ºC 760 Torr) |
| Brechungsindex | 1.5280 (estimate) |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | DMSO (Slightly), Methanol (Slightly, Heated), Pyridine (Slightly) |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 12.77±0.70(Predicted) |
| Farbe | White to Off-White |
| Merck | 14,9545 |
| InChIKey | REJLGAUYTKNVJM-GXOLHJPNNA-N |
| LogP (Verteilungskoeffizient) | 2.220 (est) |
| CAS Datenbank | 17406-45-0 |
Sicherheit & Vorschriften
| UN-Transportnummer | 1544 |
|---|---|
| Zollcode | 29329990 |
| RTECS-Nr. | XW1050000 |
| R-Sätze (R) | 23/25-22 |
| Toxizität | LD orally in rats: 900-1000 mg/kg (Wilson) |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 45-24/25-22 |
| Gefahrstoffdaten | 17406-45-0(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
This glycosidic alkaloid has been obtained from the dried leaves of Lycopersicum pimpinelli/olium (Syn. Solanum racemigerum) and also occurs in L. esculentum; L. hirsutum; L. peruvianum; L. peruvianum var. chutatum and L. putatum. The alkaloid forms colourless needles from MeOH and has a somewhat indefinite melting point about 270°C. It is laevorotatory with [α]20D - 30° (pyridine) and on hydrolysis with H2S04 yields tomatidine, I mole of galactose, 2 moles of glucose and 1 mole of xylose. The tetrasaccharide unit is known as lycotetraose. Partial hydrolysis with acid yields a series of products depending upon which, and how many, of the sugar residues are split off from the molecule. Those which have been isolated are: tomatidine lycotriose I (galactose-glucose-glucose); tomatidine lycotriose II (galactose-glucose-xylose); tomatidine lycobiose (galactose-glucose) and tomatidine-galactose.
Verwenden
Tomatine is used as an antiproliferatice agent used in the suppression of breast adenocarcinoma cells.