EQUISETIN

Base Information

• Chemical Name: EQUISETIN
• CAS No.: 57749-43-6
• Molecular Formula: C₂₂H₃₁NO₄
• Molecular Weight: 373.492
• Hs Code.: 29339900
• Mol file: 57749-43-6.mol

Synonyms:Equisetin;

Chemical Property of EQUISETIN

Chemical Property:

• Vapor Pressure: 1.07E-12mmHg at 25°C
• Melting Point: 117-118 °C
• Refractive Index: 1.587
• Boiling Point: 513.6 °C at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 264.4 °C
• PSA: 77.84000
• Density: 1.187 g/cm³
• LogP: 2.95920
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Acetone (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99.90% ^*data from raw suppliers

Equisetin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Equisetin is a fungal metabolite that has been isolated from Fusarium. It inhibits HIV-1 integrase 3’ end-processing and strand transfer activities. Equisetin inhibits the ATPase activity of rat liver mitochondria and mitoplasts stimulated by 2,4-dinitrophenol (Dnp) in a concentration-dependent manner (IC50 = ~8 nM per mg of protein for both). It also inhibits ADP-stimulated respiration and the mitochondrial transport of ATP, inorganic phosphate, and succinate. Epiequisetin is phytotoxic and inhibits the germination of various seeds and growth of young seedlings.
• Uses: The tetramic acid, equisetin, is produced by a number of species of Fusarium. Interest in equisetin emerged with reports of its inhibitory activity against HIV-1 integrase in vitro that was mechanistically distinct from previously described inhibitors. Equisetin inhibits 3' end-processing and strand transfer, as well as disintegration catalysed by either the full-length enzyme or the truncated integrase core. Equisetin is tetramic acid with antibiotic and cytotoxic activity, and a potent inhibitor of HIV-1 integrase.

Technology Process of EQUISETIN

There total 46 articles about EQUISETIN 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: 100.0%

(S)-2-({3-[(1S,2R,4aS,6R,8aR)-1,6-Dimethyl-2-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-3-oxo-propionyl}-methyl-amino)-3-hydroxy-propionic acid methyl ester (122902-79-8) → (-)-equisetin (57749-43-6)

Guidance literature:

With sodium hydride; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1021/ja00203a026

Reference yield:

(R)-2-({3-[(1S,2R,4aS,6R,8aR)-1,6-Dimethyl-2-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-3-oxo-propionyl}-methyl-amino)-3-hydroxy-propionic acid methyl ester → (-)-equisetin (57749-43-6) + 5'-epiequisetin (255377-45-8)

Guidance literature:

With sodium hydride; In dichloromethane;

DOI:10.1016/S0040-4039(01)00217-9

Reference yield:

[(1S,2R,4aS,6R,8aR)-1,6-Dimethyl-2-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-methanol (122902-71-0) → (-)-equisetin (57749-43-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / CH₂Cl₂

2: 92 percent / Zn / benzene / Heating

3: 83 percent / Dess-Martin periodinane / CH₂Cl₂

4: 96 percent / toluene / Heating

5: 99 percent / HF / acetonitrile

6: NaH / CH₂Cl₂

With hydrogen fluoride; sodium hydride; Dess-Martin periodane; zinc; In dichloromethane; toluene; acetonitrile; benzene; 1: Swern oxidation / 2: Reformatsky reaction / 3: Dess-Martin oxidation;

DOI:10.1016/S0040-4039(01)00217-9

upstream raw materials:

(S)-2-({3-[(1S,2R,4aS,6R,8aR)-1,6-Dimethyl-2-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-3-oxo-propionyl}-methyl-amino)-3-hydroxy-propionic acid methyl ester

(R)-Citronellal

[(1S,2R,4aS,6R,8aR)-1,6-Dimethyl-2-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-methanol

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-[(1E)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-carbaldehyde

Downstream raw materials:

(+)-fusarisetin A

5'-epiequisetin