77-59-8 Usage
Description
Tomatidine is the aglycone derivative of tomatine, a steroidal alkaloid belonging to the Spirosolanes and Derivatives family. It is characterized by a spirosolane skeleton and is found in the stems, leaves, and unripened fruit of tomato plants. Tomatidine is a 3beta-hydroxy steroid, resulting from the substitution of the 3beta-hydrogen of tomatidane by a hydroxy group. It forms crystals and decomposes at a temperature range of 275-280°C.
Uses
Used in Pharmaceutical Industry:
Tomatidine is used as a bioactive compound for its potential therapeutic applications. Its mild toxicity and presence in tomato plants make it a subject of interest for research and development in the pharmaceutical industry. Tomatidine may be utilized in the creation of new drugs or therapies targeting various health conditions.
Used in Agricultural Industry:
Tomatidine, being a component of tomato plants, can be used as a natural pesticide or repellent against pests that harm tomato crops. Its mild toxicity can serve as a deterrent to insects and other organisms that may damage the plants, thus contributing to the protection and preservation of tomato crops.
Used in Chemical Research:
Due to its unique chemical properties and structure, tomatidine can be used as a research subject in the field of chemistry. Scientists can study its properties, interactions, and potential applications in various chemical processes and reactions, leading to the development of new compounds or materials with specific functions or benefits.
Used in Cosmetics Industry:
Tomatidine's mild toxicity and natural origin make it a potential ingredient for use in the cosmetics industry. It could be incorporated into skincare products, hair care formulations, or other cosmetic applications for its potential benefits, such as anti-aging, moisturizing, or protective properties.
Pharmaceutical Properties
Red, ripe tomatoes have somewhat reduced amounts of tomatine and tomatidine. Both tomatine and tomatidine possess antimicrobial, antifungal and antiviral properties. Tomatidine has been shown to exhibit anti-virulence activity against normal strains of Staphylococcus aureus as well as the ability to potentiate the effect of aminoglycoside antibiotics. Recent studies have shown that tomatidine stimulates mTORC1 signaling and anabolism, leading to accumulation of protein and mitochondria, and ultimately, cell growth. Furthermore, in mice, tomatidine has been shown to increase skeletal muscle mTORC1 signaling, reduce skeletal muscle atrophy, enhance recovery from skeletal muscle atrophy, stimulate skeletal muscle hypertrophy, and increase strength and exercise capacity. Tomatidine has also been shown to significantly inhibit cholesterol ester accumulation induced by acetylated LDL in human monocyte-derived macrophages in a dose-dependent manner. Tomatidine also inhibits cholesterol ester formation in Chinese hamster ovary cells overexpressing acyl-CoA:cholesterol acyl-transferase (ACAT)-1 or ACAT-2, suggesting that tomatidine suppresses both ACAT-1 and ACAT-2 activities. The oral administration of tomatidine to apoE-deficient mice significantly reduces levels of serum cholesterol, LDL-cholesterol, and the size of atherosclerotic lesions.
Purification Methods
Tomatidine forms plates from EtOAc. It is also purified by dissolving 80mg in *C6H6 and applying to an Al2O3 column (3.0g) and eluting with *C6H6, evaporating and recrystallising the residue three times from EtOAc. The hydrochloride has m 265-270o from EtOH and [] D 25 -5o (MeOH). [IR: Uhle J Am Chem Soc 83 1460 1961, Kessar et al. Tetrahedron 27 2869 1971, Schreiber & Adams Experientia 17 13 1961, Beilstein 27 III/IV 1950.]
Check Digit Verification of cas no
The CAS Registry Mumber 77-59-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 7 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 77-59:
(4*7)+(3*7)+(2*5)+(1*9)=68
68 % 10 = 8
So 77-59-8 is a valid CAS Registry Number.
InChI:InChI=1/C27H45NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28-29H,5-15H2,1-4H3
77-59-8Relevant articles and documents
Enzymatic liberation of lycotetraose from the Solanum glycoalkaloid α-tomatine
Woods, Katherine,Hamilton, Chris J.,Field, Robert A.
, p. 2325 - 2328 (2004)
The branched tetrasaccharide, O-β-D-glucopyranosyl-(1→2)-O- [β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4) -D-galactose (lycotetraose) is a key constituent of many biologically interesting natural products. Described herein is a convenient enzymatic preparation of lycotetraose from the readily available Solanum glycoalkaloid α-tomatine. The preparation makes use of the recombinant endo-glycosidase, tomatinase, from the plant pathogen Fusarium oxysporum f. sp. lycopersici.
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Uhle,Moore
, p. 6412 (1954)
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Synthesis of spiroaminoketal groupings from Solanum alkaloids.
SCHREIBER,ADAM
, p. 13 - 14 (1961)
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Concise large-scale synthesis of tomatidine, a potent antibiotic natural product
Boudreault, Pierre-Luc,Normandin, Chad
, (2021/10/12)
Tomatidine has recently generated a lot of interest amongst the pharmacology, medicine, and biology fields of study, especially for its newfound activity as an antibiotic agent capable of targeting multiple strains of bacteria. In the light of its low natural abundance and high cost, an efficient and scalable multi-gram synthesis of tomatidine has been developed. This synthesis uses a Suzuki–Miyaura-type coupling reaction as a key step to graft an enantiopure F-ring side chain to the steroidal scaffold of the natural product, which was accessible from low-cost and commercially available diosgenin. A Lewis acid-mediated spiroketal opening followed by an azide substitution and reduction sequence is employed to generate the spiroaminoketal motif of the natural product. Overall, this synthesis produced 5.2 g in a single pass in 15 total steps and 15.2% yield using a methodology that is atom economical, scalable, and requires no flash chromatography purifications.
PRODUCTION METHOD OF TOMATIDINE
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Paragraph 0041-0043, (2019/01/05)
PROBLEM TO BE SOLVED: To provide a production method of tomatidine which can be used as a health food product or a medicament by converting tomatine which is one kind of gluco alkaloids included in a tomato plant body into tomatidine which has no toxicity and for which a prevention effect of age-related muscle atrophy can be expected. SOLUTION: The invention is configured so that, a leaf, a stem, a lateral bud, a petal, an immature fruit, and a root are cut, or are pulverized after drying, then water is added to the pulverized object per weight, the amount of the water being 3-15 times of the pulverized object, then an acid solution is added for adjusting pH of the mixture of the pulverized object and water to 2-5, then, the mixture is agitated and mixed for 30-120 minutes under temperature of room temperature to 80°C, for extracting tomatine including dehydro tomatine of glycosylated alkaloid, then an alkali solution is added to the extract then the mixture of the alkali solution and the extract is adjusted so that pH becomes 8 or higher and less than 10 in room temperature for deposition of tomatine, then after collecting deposited tomatine, then the deposited tomatine is dissolved in an acid solution of 0.5-2N, then the mixture of the acid solution and the deposited tomatine is heated for 1-4 hours at 60°C-80°C for converting the tomatine into tomatidine, then using the alkali solution again for adjusting the pH of the mixture to become 8 or more and less than 10 for deposition of the tomatidine, then the deposited tomatidine is collected, then the deposited tomatidine is dissolved in an ethanol solution whose density is 70% or more for deposition of mixed impurities for removing the impurities, then the ethanol is evaporated. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
