TOMATINE
- CAS NO.:17406-45-0
- Empirical Formula: C50H83NO21
- Molecular Weight: 1034.19
- MDL number: MFCD00016888
- EINECS: 241-429-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-15 19:19:13
What is TOMATINE?
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.
Chemical properties
Faintly beige powder
The Uses of TOMATINE
Tomatine is used as an antiproliferatice agent used in the suppression of breast adenocarcinoma cells.
The Uses of TOMATINE
Precipitating agent for steroids.
What are the applications of Application
Tomatine is an antiproliferatve agent of breast adenocarcinoma cells
Definition
ChEBI: A steroid alkaloid that is tomatidine in which the hydroxy group at position 3 is linked to lycotetraose, a tetrasaccharide composed of two units of D-glucose, one unit of D-xylose, and one unit of D-galac ose.
Purification Methods
Tomatine is recrystallised from MeOH, EtOH, aqueous EtOH or dioxane/NH3. It is almost insoluble in pet ether, Et2O or H2O. [Reichstein Angew Chem 74 887 1962, Beilstein 27 III/IV 1954.]
References
Fontaine et al., Arch. Biochem., 18,467 (1948)
Kuhn, Low., Ber., 81, 552 (1948)
Kuhn, Low, Gauhe., ibid, 83,448 (1950)
Fontaine et al., Arch. Biochem., 27,461 (1950)
Fontaine et al., J. Amer. Chern. Soc., 73, 878 (1951)
Kuhn, Low, Trischmann., Angew. Chern., 68, 212 (1956)
Kuhn et al., Ber., 90, 203 (1957)
Properties of TOMATINE
Melting point: | 300-305°C |
Boiling point: | 806.69°C (rough estimate) |
alpha | D20 -18° (c = 0.55 in pyridine) |
Density | 1.48±0.1 g/cm3 (20 ºC 760 Torr) |
refractive index | 1.5280 (estimate) |
storage temp. | 2-8°C |
solubility | DMSO (Slightly), Methanol (Slightly, Heated), Pyridine (Slightly) |
form | Solid |
pka | 12.77±0.70(Predicted) |
color | White to Off-White |
Merck | 14,9545 |
CAS DataBase Reference | 17406-45-0 |
Safety information for TOMATINE
Computed Descriptors for TOMATINE
New Products
4-Aminotetrahydropyran-4-carbonitrile Hydrochloride (R)-3-Aminobutanenitrile Hydrochloride 4-AMINO-TETRAHYDRO-PYRAN-4-CARBOXYLIC ACID HCL 4-(Dimethylamino)tetrahydro-2H-pyran-4-carbonitrile 3-((Dimethylamino)methyl)-5-methylhexan-2-one oxalate 1,4-Dioxa-8-azaspiro[4.5]decane 5-Bromo-2-nitropyridine Nimesulide BP Aceclofenac IP/BP/EP Diclofenac Sodium IP/BP/EP/USP Mefenamic Acid IP/BP/EP/USP Ornidazole IP Diclofenac Potassium SODIUM AAS SOLUTION ZINC AAS SOLUTION BUFFER SOLUTION PH 10.0(BORATE) GOOCH CRUCIBLE SINTERED AQUANIL 5 BERYLLIUM AAS SOLUTION 2-Bromo-1-(bromomethyl)-3-chloro-5-nitrobenzene 2-Bromo-3-nitroaniline N-(3-Hydroxypropyl)-N-methylacetamide 3-Bromo-6-chloropyridazine 4-ethyl-3-nitrobenzoic acidRelated products of tetrahydrofuran
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