17406-45-0 Usage
Description
Tomatine is a glycosidic alkaloid found in various tomato species, including Lycopersicum pimpinelli/olium (Syn. Solanum racemigerum), L. esculentum, L. hirsutum, L. peruvianum, L. peruvianum var. chutatum, and L. putatum. It forms colorless needles from MeOH and has a somewhat indefinite melting point around 270°C. Tomatine is a steroid alkaloid 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 appears as a faintly beige powder.
Uses
Used in Pharmaceutical Industry:
Tomatine is used as a precipitating agent for steroids, aiding in the isolation and purification of these compounds for various pharmaceutical applications.
Used in Cancer Research:
Tomatine is used as an antiproliferative agent for the suppression of breast adenocarcinoma cells, showcasing its potential as a therapeutic agent in cancer treatment.
Used in Chemical Analysis:
Tomatine can be employed in chemical analysis, as its partial hydrolysis with acid yields a series of products depending on which and how many sugar residues are split off from the molecule. This allows for the study and identification of various related compounds, such as tomatidine lycotriose I (galactose-glucose-glucose), tomatidine lycotriose II (galactose-glucose-xylose), tomatidine lycobiose (galactose-glucose), and tomatidine-galactose.
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.
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)
Check Digit Verification of cas no
The CAS Registry Mumber 17406-45-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,7,4,0 and 6 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 17406-45:
(7*1)+(6*7)+(5*4)+(4*0)+(3*6)+(2*4)+(1*5)=100
100 % 10 = 0
So 17406-45-0 is a valid CAS Registry Number.
InChI:InChI=1/C50H83NO21/c1-20-7-12-50(51-15-20)21(2)32-28(72-50)14-26-24-6-5-22-13-23(8-10-48(22,3)25(24)9-11-49(26,32)4)65-45-40(63)37(60)41(31(18-54)68-45)69-47-43(71-46-39(62)36(59)34(57)29(16-52)66-46)42(35(58)30(17-53)67-47)70-44-38(61)33(56)27(55)19-64-44/h20-47,51-63H,5-19H2,1-4H3/t20-,21-,22-,23-,24+,25-,26-,27+,28-,29+,30+,31+,32-,33-,34+,35+,36-,37+,38+,39+,40+,41-,42-,43+,44-,45+,46-,47-,48-,49-,50-/m0/s1