RUTARETIN

Base Information

• Chemical Name: RUTARETIN
• CAS No.: 13895-92-6
• Molecular Formula: C₁₄H₁₄O₅
• Molecular Weight: 262.262
• Mol file: 13895-92-6.mol

Synonyms:7H-Furo[3,2-g][1]benzopyran-7-one,2,3-dihydro-9-hydroxy-2-(1-hydroxy-1-methylethyl)-, (-)- (8CI);7H-Furo[3,2-g][1]benzopyran-7-one,2,3-dihydro-9-hydroxy-2-(1-hydroxy-1-methylethyl)-, (S)-; (-)-Racemol;(-)-Rutaretin; Racemol; Rutaretin

Chemical Property of RUTARETIN

Chemical Property:

• PSA: 79.90000
• LogP: 1.57300

Purity/Quality:

≥97% ^*data from raw suppliers

Rutaretin 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of RUTARETIN

There total 9 articles about RUTARETIN 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: 40.1%

4-(2,3-Dihydroxy-3-methyl-butyl)-2,2-diphenyl-[1,3]dioxolo[4,5-h]chromen-8-one → rutaretin (159979-69-8,13895-92-6)

Guidance literature:

With boron trichloride; In dichloromethane; 1) -77 deg C, 20 min; 2) -77 deg C --> room temperature, 20 min;

Reference yield:

2'(S)-rutaretin-1''-(hydrogen sulphate), potassium salt → rutaretin (13895-92-6)

Guidance literature:

With hydrogenchloride; at 95 ℃; for 1.5h;

DOI:10.1016/S0031-9422(00)85044-X

Reference yield:

2,2-Diphenyl-[1,3]dioxolo[4,5-h]chromen-8-one (159979-62-1) → rutaretin (159979-69-8,13895-92-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 92.2 percent / NaOMe / Heating

2: 78.7 percent / sodium carbonate / acetone / Heating

3: 72.1 percent / N,N-diethylaniline / 5 h / 180 °C

4: dihydroquinidine 9-O-(9'-phenanthryl) ether, K₃, sodium carbonate, K₂2(OH)4> / H₂O; 2-methyl-propan-2-ol / 48 h / Ambient temperature

5: 40.1 percent / borom trichloride / CH₂Cl₂ / 1) -77 deg C, 20 min; 2) -77 deg C --> room temperature, 20 min

With dihydroquinidine 0-O-(9'-phenanthryl) ether; K2; sodium methylate; boron trichloride; sodium carbonate; N,N-diethylaniline; potassium hexacyanoferrate(III); In dichloromethane; water; acetone; tert-butyl alcohol;

upstream raw materials:

(E)-3-(4-Hydroxy-3,5-dimethoxy-phenyl)-acrylic acid (2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[1-(9-hydroxy-7-oxo-2,3-dihydro-7H-furo[3,2-g]chromen-2-yl)-1-methyl-ethoxy]-tetrahydro-pyran-2-ylmethyl ester

2,2-Diphenyl-[1,3]dioxolo[4,5-h]chromen-8-one

(E)-3-(4-Hydroxy-2,2-diphenyl-benzo[1,3]dioxol-5-yl)-acrylic acid methyl ester

4-(3-Methyl-but-2-enyl)-2,2-diphenyl-[1,3]dioxolo[4,5-h]chromen-8-one

Refernces

• 1、 Abyshev, A. Z.,Agaev, E. M.,Balabudkin, M. A.. "RUTARIN FROM THE ROOTS OF Seseli grandivittatum". . p. 250 - 251. Retrieved 1993.
• 2、 Reisch, Johannes,Achenbach, Stefan H.. "A FURANOCOUMARIN GLUCOSIDE FROM STEMBARK OF SKIMMIA JAPONICA". . p. 4376 - 4377. Retrieved 2007/10/02.