TOMATINE

TOMATINE Basic information
Health Benifits Tomatine Toxin Symptoms
Product Name:TOMATINE
Synonyms:TOMATIN;TOMATINE;a’’-tomatidine;alpha-tomatine;beta-d-galactopyranoside,(3beta,5alpha,22beta,25s)-spirosolan-3-ylo-beta-d-gl;tomatidine,glycoside;ucopyranosyl-(1-2)-o-(beta-d-xylopyranosyl-(1-3))-o-beta-d-glucopyranosyl-(1-4;LYCOPERISCIN
CAS:17406-45-0
MF:C50H83NO21
MW:1034.19
EINECS:241-429-5
Product Categories:Alkaloids;Alkaloids (Others);Biochemistry;Glycosides;Steroidglycosides;Steroids;Sugars
Mol File:17406-45-0.mol
TOMATINE Structure
TOMATINE Chemical Properties
Melting point 300-305°C
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 temp. 2-8°C
solubility DMSO (Slightly), Methanol (Slightly, Heated), Pyridine (Slightly)
form Solid
pka12.77±0.70(Predicted)
color White to Off-White
Merck 14,9545
LogP2.220 (est)
CAS DataBase Reference17406-45-0
Safety Information
Hazard Codes Xn
Risk Statements 23/25-22
Safety Statements 45-24/25-22
RIDADR 1544
RTECS XW1050000
HS Code 29329990
Hazardous Substances Data17406-45-0(Hazardous Substances Data)
ToxicityLD orally in rats: 900-1000 mg/kg (Wilson)
MSDS Information
TOMATINE Usage And Synthesis
Health Benifits

Tomatine (sometimes called tomatin or lycopersicin) is a glycoalkaloid, found in the stems and leaves of tomato plants, and in the fruits at much lower concentrations. It has fungicidal, antimicrobial, and insecticidal properties. Chemically pure tomatine is a white crystalline solid at standard temperature and pressure. Tomatine, as well as the closely related aglycon (or aglycone) derivative tomatidine have been shown to have multiple health benefits.
Tomatine is 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-galactose. It has a role as an immunological adjuvant, a phytotoxin and an antifungal agent. It is a steroid alkaloid, a tetrasaccharide derivative, an alkaloid antibiotic and a glycoside. It derives from a tomatidine.

Tomatine Toxin Symptoms

The possible risks of tomatine for humans have not been formally studied, so no NOAEL can be deduced. The toxicity of tomatine has only been studied on laboratory animals. The symptoms of acute tomatine poisoning in animals are similar to the symptoms of poisoning by solanine, a potato glycoalkaloid. These symptoms include vomiting, diarrhea, abdominal pain, drowsiness, confusion, weakness, and depression. Generally, tomatine is regarded to cause less toxic effect to mammals than other alkaloids such as solanine. The amount of tomatine absorbed by the human body as well as the possible metabolism is unknown. There is no evidence that consumption of tomatoes causes acute toxic or genotoxic effects.

DescriptionThis 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 PropertiesFaintly beige powder
UsesPrecipitating agent for steroids.
UsesTomatine is used as an antiproliferatice agent used in the suppression of breast adenocarcinoma cells.
DefinitionChEBI: 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.
targetNF-kB | PI3K | Akt | ERK | MMP(e.g.TIMP) | AP-1 | ROS | Calcium Channel
Purification MethodsTomatine 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.]
ReferencesFontaine 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)





TOMATINE Preparation Products And Raw materials
Preparation ProductsTOMATIDINE
2,6,10,14-TETRAMETHYLOCTADECANE 5-ALPHA-PREGNANE 2-AMINOUNDECANE 3-CYCLOHEXYL-PROPYLAMINE 2-N-PROPYLPIPERIDINE 12-AMINO-1-DODECANOL 1,12-DIMETHOXYDODECANE 1-BUTOXYETHOXY-2-PROPANOL 3-BUTOXY-PROPIONALDEHYDE DIETHYL ACETAL 1,12-OCTADECANEDIOL ETHYLBETA-D-GALACTOPYRANOSIDE DI(PROPYLENE GLYCOL) PROPYL ETHER 2-(TETRADECYLOXY)ETHANOL N-isobutyl-sec-butylamine PROPYLENE GLYCOL BUTYL ETHER 2,6,10,14-TETRAMETHYLHEPTADECANE 2-AMINONONADECANE 2-(1-methylethyl)piperidine

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