Tigogenin

Base Information

• Chemical Name: Tigogenin
• CAS No.: 77-60-1
• Molecular Formula: C27H44O3
• Molecular Weight: 416.645
• Hs Code.: 2932999099
• European Community (EC) Number: 201-041-9
• UNII: 4SMU15RR44
• DSSTox Substance ID: DTXSID40903920
• Nikkaji Number: J4.209I
• Wikidata: Q27108442
• Metabolomics Workbench ID: 35103
• ChEMBL ID: CHEMBL43871
• Mol file: 77-60-1.mol

Synonyms:epi-sarsasapogenin;epismilagenin;PYM 50028;PYM-50028;PYM50028;sarsaponin;sarsasapogenin;sarsasapogenin, (3beta,5alpha,25R)-isomer;sarsasapogenin, (3beta,5alpha,25S)-isomer;sarsasapogenin, (3beta,5beta)-isomer;sarsasapogenin, (3beta,5beta,25R)-isomer;sarsasapogenin, (3beta,5beta,25S)-isomer;smilagenin;tigogenin

Chemical Property of Tigogenin

Chemical Property:

• Appearance/Colour: White, micro-cryst. powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 202-204 °C
• Refractive Index: 1.552
• Boiling Point: 516.6 °C at 760 mmHg
• PKA: 15.14±0.70(Predicted)
• Flash Point: 266.2 °C
• PSA: 38.69000
• Density: 1.11 g/cm³
• LogP: 5.79380
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly)
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 416.32904526
• Heavy Atom Count: 30
• Complexity: 694

Purity/Quality:

97% ^*data from raw suppliers

Tigogenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CCC(C6)O)C)C)C)OC1
• Isomeric SMILES: C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@@H]6[C@@]5(CC[C@@H](C6)O)C)C)C)OC1
• Description: Tigogenin is a steroidal sapogenin that has been found in A. sisalana and has diverse biological activities. It increases the proliferation rate of, as well as mRNA levels of genes encoding the osteoblastic differentiation markers Cbfa1, collagen type I, and osteocalcin in, mouse bone marrow stromal cells (BMSCs) in a concentration-dependent manner. It also increases matrix calcium deposition in BMSCs when used at concentrations of 30 and 90 μM. Tigogenin is active against the fungus A. fumigatus (MIC50 = 16 μg/ml). It inhibits carrageenan-induced paw edema in rats when administered at a dose of 4.2 μg/kg.
• Uses: Tigogenin is a saponin structurally similar to Diosgenin (D484700) and acts as a natural plant steroid which induces apoptosis in rheumatoid arthritic fibroblast-like synoviocytes.

Technology Process of Tigogenin

There total 98 articles about Tigogenin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

C27H43NO4 → Neotigogenin (77-60-1,126-18-1,126-19-2,428-41-1,470-00-8,470-01-9,470-03-1,546-41-8,6788-40-5,7050-46-6,16653-88-6,19043-98-2,20460-38-2,31356-48-6,36027-61-9,36136-35-3,75172-34-8,78964-18-8,82597-74-8,107380-02-9,119677-72-4) + neotigogenone (5159-14-8)

Guidance literature:

In solid; for 168h; Irradiation;

DOI:10.1246/cl.1996.217

Reference yield: 33.1%

26-O-β-D-glucopyransoyl-(25S)-5β-furostane-3β,22ξ,26-triol 3-O-[α-L-rhamnopyranosyl (1->)]-β-D-glucopyranside → Neotigogenin (77-60-1,126-18-1,126-19-2,428-41-1,470-00-8,470-01-9,470-03-1,546-41-8,6788-40-5,7050-46-6,16653-88-6,19043-98-2,20460-38-2,31356-48-6,36027-61-9,36136-35-3,75172-34-8,78964-18-8,82597-74-8,107380-02-9,119677-72-4)

Guidance literature:

With hydrogenchloride; In ethanol; for 3h; Heating;

DOI:10.1248/cpb.45.81

Reference yield:

3-O-β-D-glucopyranosyl-(1->3)[β-D-fucopyranosyl-(1->2)]-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl-(25R),5α-furostan-3β,22α,26-triol-26-O-β-D-glucopyranoside (1282510-01-3) → tigogenin (77-60-1) + D-Fucose (3615-37-0,478518-52-4) + D-glucose (50-99-7) + D-Galactose (59-23-4)

Guidance literature:

With sulfuric acid; water; In ethanol; for 2h; Reflux;

DOI:10.1007/s10600-010-9579-4

upstream raw materials:

ethanol

(25R)-22-ethoxy-5α,22αH-furostan-3β,26-diol

acetic acid

(25R)-5α-furost-22ξ-ene-3β,26-diol

Downstream raw materials:

(25R)-5β-spirostan-3α-ol acetate

O-(toluene-4-sulfonyl)-epismilagenin

tomatidine acetate

tomatidine

Refernces

"One-pot" reductive lactone alkylation provides a concise asymmetric synthesis of chiral isoprenoid targets

10.1021/ol401801g

The study presents an efficient "one-pot" reductive lactone alkylation method for synthesizing chiral isoprenoid compounds, which are significant structural fragments in natural products like pheromones, fragrances, and vitamins. The process involves nucleophilic addition of organometallic reagents, such as alkyllithiums or Grignard reagents, to lactones, followed by in situ reduction of the intermediate keto-alcohol using a modified Clemmensen reduction with TMSCl and Zn. The method was successfully applied to various lactones, including (R)-3-methylbutyrolactone and (R)-4-methyl-δ-valerolactone, derived from tigogenin, and demonstrated high yields and enantiomeric purity. The synthesized alcohols were further utilized to create commercially important compounds like the fragrance Rosaphen and the side chains of Zaragozic acid C and vitamin E, showcasing the versatility and potential for scale-up of this synthetic approach.