470-01-9

Basic information

• Product Name: NEOTIGOGENIN
• Synonyms: NEOTIGOGENIN;(25S)-5α-Spirostan-3β-ol;Trigonegenin A
• CAS NO: 470-01-9
• Molecular Formula: C27H44O3
• Molecular Weight: 416.63646
• Mol File: 470-01-9.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 516.6°Cat760mmHg
• Flash Point: 266.2°C
• Appearance: /
• Density: 1.11g/cm³
• CAS DataBase Reference: NEOTIGOGENIN(CAS DataBase Reference)
• NIST Chemistry Reference: NEOTIGOGENIN(470-01-9)
• EPA Substance Registry System: NEOTIGOGENIN(470-01-9)

Safety Data

• Hazardous Substances Data: 470-01-9(Hazardous Substances Data)

Usage

Description

Neotigogenin is a steroidal saponin, a chemical compound found in various plant species such as Agave sisalana, Agave americana, and Yucca gloriosa. It is known for its potential pharmaceutical properties, including its ability to inhibit the growth of cancer cells and its anti-inflammatory effects. Neotigogenin has also been studied for its potential as a precursor for the synthesis of steroid drugs. Its structure and bioactivity make it a subject of interest in the fields of pharmacology and medicinal chemistry for the development of new drugs and treatments. Additionally, it is considered as a potential biopesticide due to its insecticidal properties when extracted from Agave sisalana.

Uses

Used in Pharmaceutical Industry:
Neotigogenin is used as an anticancer agent for its ability to inhibit the growth of cancer cells. It is also used for its anti-inflammatory effects, making it a potential candidate for the development of new drugs and treatments in the pharmaceutical industry.
Used in Drug Synthesis:
Neotigogenin is used as a precursor for the synthesis of steroid drugs, contributing to the development of new pharmaceutical compounds.
Used in Biopesticide Industry:
Neotigogenin is used as a potential biopesticide due to its insecticidal properties when extracted from Agave sisalana, offering an alternative to chemical pesticides in the agricultural sector.

Upstream product

• 512-07-2 (25R)-5β-spirostan-3-one 
• 6859-63-8 (25S)-5α-furost-20(22)-ene-3β,26-diol 
• 39941-51-0 diuranthoside A 
• 79974-46-2 Chloromaloside D 
• 106505-70-8 (23S,25S)-23-bromo-spirost-4-en-3-one 
• 4948-43-0 (4S,5′S,6aS,8aS,9S,10R,11aS)-5′,6a,8a,9-tetramethyldocosahydrospiro[naphtho[2′,1′:4,5]indeno[2,1-b]furan-10,2′-pyran]-4-yl acetate 
• 512-04-9 diosgenin 
• 1180-12-7 Diosgeninmonoacetat 
• 6870-79-7 (25R)-spirost-4-ene-3-one 
• 512-06-1 yamogenin 
• 75556-25-1 tomatoside B 

Downstream Products

• 66934-60-9 tomatidine acetate 
• 77-59-8 tomatidine 
• 66934-60-9 (22R,25R)-3β-acetoxy-(5α)-spirosolane 
• 2530-07-6 tigogenyl acetate 
• 28154-24-7 O-β-tigogenyl glucoside tetraacetate 
• 69292-75-7 C₅₃H₇₈O₂₀ 
• 4965-79-1 O-(toluene-4-sulfonyl)-epismilagenin 
• 2530-07-6 (25R)-5β-spirostan-3α-ol acetate 

Relevant articles and documents

Concise large-scale synthesis of tomatidine, a potent antibiotic natural product

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.

Gram-Scale Synthesis of Tomatidine, a Steroid Alkaloid with Antibiotic Properties Against Persistent Forms of Staphylococcus aureus

We herein describe the first diastereoselective synthesis of the Solanum alkaloid tomatidine 1. The synthesis has been accomplished in 11 steps and 24.9 % overall yield (longest linear sequence). This methodology, which involves a convergent synthon insertion followed by a sequence of ring opening/nitrogen substitution/ring closing, allowed the generation of 1 on > 2 g scale. The synthetic challenge with the diastereoselective generation of the unusual spiroaminoketal moiety was solved through a combined azide reduction/addition sequence. The first diastereoselective synthesis of the phytosteroid yamogenin is also reported. Tomatidine has shown promising antibiotic properties against persistent forms of Staphylococcus aureus (S. aureus) and methicillin-resistant S. aureus (MRSA). In particular, it possesses the unique ability to kill persistent forms of S. aureus and MRSA while simultaneously potentiating the antibiotic efficacy of aminoglycoside antibiotics against wild type strains of the bacteria.

TIMOSAPONIN COMPOUNDS

Provided herein are timosaponin compounds of Frmula I, II, IIΙ, I', II' and IIΙ', pharmaceutical compositions comprising the coumpounds, and processes of preparation thereof. Also provided are uses of said timosaponin compounds for preparing medicament for the treatment of diseases associated with beta-amyloid in hosts or subjects in need thereof.