Tomatine [for Cholesterol assay]
alpha-tomatine · TOMATIN · Tomatine [for Cholesterol assay] · omatine · Tomatie · TOMATINE · NSC 9223 · a-Tomatine
![Tomatine [for Cholesterol assay] molecular structure](/img/chemical/5513.png)
Identifiers & Physical Properties
| CAS No. | 17406-45-0 |
|---|---|
| Molecular formula | C50H83NO21 |
| Average molar mass | 1,034.2 g/mol |
| Monoisotopic mass | 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 |
Chemical & Physical Properties
| XLogP | -0.7 |
|---|---|
| Topological polar surface area | 338 |
| Hydrogen bond donors | 13 |
| Hydrogen bond acceptors | 22 |
| Rotatable bonds | 11 |
| Heavy atoms | 72 |
| Formal charge | 0 |
| Complexity | 1,840 |
| Melting point | 263 - 267 °C300-305°C |
| Physical Description | Solid |
| alpha | D20 -18° (c = 0.55 in pyridine) |
| Boiling point | 806.69°C (rough estimate) |
| Density | 1.48±0.1 g/cm3 (20 ºC 760 Torr) |
| Refractive index | 1.5280 (estimate) |
| Storage conditions | 2-8°C |
| Solubility | DMSO (Slightly), Methanol (Slightly, Heated), Pyridine (Slightly) |
| Physical state | Solid |
| pKa (acidity coefficient) | 12.77±0.70(Predicted) |
| Color | White to Off-White |
| Merck | 14,9545 |
| InChIKey | REJLGAUYTKNVJM-GXOLHJPNNA-N |
| LogP (partition coefficient) | 2.220 (est) |
| CAS DataBase Reference | 17406-45-0 |
| EWG's Food Scores | 1 |
| FDA UNII | 31U6547O08 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302 |
| GHS precautionary statements | P264-P270-P301+P312-P330-P501 |
| Hazard symbols | Xn |
| Risk statements (R) | 23/25-22 |
| Safety statements (S) | 45-24/25-22 |
| UN transport number | 1544 |
| RTECS number | XW1050000 |
| Customs code | 29329990 |
| Hazardous substances data | 17406-45-0(Hazardous Substances Data) |
| Toxicity | LD orally in rats: 900-1000 mg/kg (Wilson) |
Safety & Regulations
| RTECS number | XW1050000 |
|---|---|
| UN transport number | 1544 |
| Customs code | 29329990 |
| Toxicity | LD orally in rats: 900-1000 mg/kg (Wilson) |
| Risk statements (R) | 23/25-22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn |
| Safety statements (S) | 45-24/25-22 |
| GHS hazard statements | H302 |
| GHS precautionary statements | P264-P270-P301+P312-P330-P501 |
| Hazardous substances data | 17406-45-0(Hazardous Substances Data) |
Applications & Uses
Description
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.
Uses
Tomatine is used as an antiproliferatice agent used in the suppression of breast adenocarcinoma cells.
Uses
Precipitating agent for steroids.