IMPERATORIN

Base Information

• Chemical Name: IMPERATORIN
• CAS No.: 148-83-4
• Molecular Formula: C₁₉H₂₂O₃
• Molecular Weight: 298.382
• Mol file: 148-83-4.mol

Synonyms:2H-1-Benzopyran-2-one,6-(3,7-dimethyl-2,6-octadienyl)-7-hydroxy-, (E)-; 2H-1-Benzopyran-2-one,6-[(2E)-3,7-dimethyl-2,6-octadienyl]-7-hydroxy- (9CI); Coumarin,6-(3,7-dimethyl-2,6-octadienyl)-7-hydroxy-, (E)- (8CI); Ostruthin (6CI);6-Geranyl-7-hydroxycoumarin; NSC 83434; Ostruthine

Chemical Property of IMPERATORIN

Chemical Property:

• Vapor Pressure: 4.84E-10mmHg at 25°C
• Melting Point: 117-119°
• Boiling Point: 485.3 °C at 760 mmHg
• Flash Point: 200.3 °C
• PSA: 50.44000
• Density: 1.116 g/cm³
• LogP: 4.73380
• Storage Temp.: ?20°C

Purity/Quality:

98%min ^*data from raw suppliers

6-Geranyl-7-hydroxycoumarin ≥95% (LC/MS-ELSD) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of IMPERATORIN

There total 6 articles about IMPERATORIN 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: 82.0%

7-Benzyloxy-6-((E)-3,7-dimethyl-octa-2,6-dienyl)-chromen-2-one (107052-39-1) → ostruthin (13319-09-0,148-83-4)

Guidance literature:

With hydrogen; nickel; In ethanol;

DOI:10.1039/c39860001264

Reference yield: 36.0%

7-hydroxy-2H-chromen-2-one (93-35-6) + Geraniol (106-24-1) → ostruthin (13319-09-0,148-83-4)

Guidance literature:

With aluminum oxide; In 5,5-dimethyl-1,3-cyclohexadiene; at 160 ℃; for 2h;

Reference yield:

7-(benzyloxy)-2H-chromen-2-one (31005-04-6) → ostruthin (13319-09-0,148-83-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / sodium methoxide / 5 h / Heating

2: 1.) potassium carbonate / 1) acetone, 30 min; 2) acetone, reflux, 8 h

3: 2.) H₂ / 2.) Raney nickel / 1) diethylaniline, reflux, 5 h; 2) ethanol, room temperature

With hydrogen; sodium methylate; potassium carbonate; nickel;

upstream raw materials:

7-Benzyloxy-6-((E)-3,7-dimethyl-octa-2,6-dienyl)-chromen-2-one

methyl (E)-4'-benzyloxy-2'-(3,7-dimethylocta-2,6-dienyloxy)cinnamate

7-(benzyloxy)-2H-chromen-2-one

(E)-3-(4-Benzyloxy-2-hydroxy-phenyl)-acrylic acid methyl ester

Downstream raw materials:

styphnic acid

recorcinol

6-geranyl-7-hydroxy-8(N-4'-phenylpiperazinomethyl)coumarin

Refernces

• 1、 Cairns, Nicholas,Harwood, Laurence M.,Astles, David P.. "Tandem Thermal Claisen-Cope Rearrangements of Coumarate Derivatives. Total Syntheses of the Naturally Occuring Coumarins: Suberosin, Demethylsuberosin, Ostrithin, Balsamiferone and Gravelliferone". . p. 3101 - 3108. Retrieved 2007/10/02.