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)

pka

12.77±0.70(Predicted)

form 

Solid

color 

White to Off-White

Merck 

14,9545

LogP

2.220 (est)

CAS DataBase Reference

17406-45-0

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 Data

17406-45-0(Hazardous Substances Data)

Toxicity

LD orally in rats: 900-1000 mg/kg (Wilson)

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.

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]²⁰_D - 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

Uses

Tomatine is used as an antiproliferatice agent used in the suppression of breast adenocarcinoma cells.

Uses

Precipitating agent for steroids.

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.

target

NF-kB | PI3K | Akt | ERK | MMP(e.g.TIMP) | AP-1 | ROS | Calcium Channel

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)

TOMATINE(17406-45-0)Related Product Information

• DI(PROPYLENE GLYCOL) BUTYL ETHER
• 2-heptyltetrahydrofuran
• 2-(OCTADECYLOXY)ETHANOL
• PROPYLENE GLYCOL BUTYL ETHER
• 12-AMINO-1-DODECANOL
• Dulcitol
• 1,12-OCTADECANEDIOL
• TOMATINE
• Dihydrocholesterol
• 2,6,8-TRIMETHYL-4-NONANOL
• PHYTANE
• 5α-Cholestane
• 2-(DODECYLOXY)ETHANOL
• Triethylene glycol
• TOMATIDINE
• 3-O-HEXADECYL-SN-GLYCEROL
• 1-BUTOXYETHOXY-2-PROPANOL
• 3-BUTOXY-PROPIONALDEHYDE DIETHYL ACETAL