Kobusin

Base Information

• Chemical Name: Kobusin
• CAS No.: 36150-23-9
• Molecular Formula: C₂₁H₂₂O₆
• Molecular Weight: 370.402
• UNII: CUR4HUP6JQ
• DSSTox Substance ID: DTXSID00189723
• Nikkaji Number: J17.516A
• Wikidata: Q83061925
• Metabolomics Workbench ID: 136101
• ChEMBL ID: CHEMBL462822
• Mol file: 36150-23-9.mol

Synonyms:kobusin

Chemical Property of Kobusin

Chemical Property:

• Vapor Pressure: 7.05E-10mmHg at 25°C
• Boiling Point: 506.4°Cat760mmHg
• Flash Point: 208.9°C
• PSA: 55.38000
• Density: 1.265g/cm³
• LogP: 3.50770
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 370.14163842
• Heavy Atom Count: 27
• Complexity: 515

Purity/Quality:

≥98% ^*data from raw suppliers

(+)-Kobusin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2C3COC(C3CO2)C4=CC5=C(C=C4)OCO5)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)[C@@H]2[C@H]3CO[C@@H]([C@H]3CO2)C4=CC5=C(C=C4)OCO5)OC
• Uses: (+)-Kobusin is a lignan isolated from the bark of Magnolia kobus and inhibits lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production.

Technology Process of Kobusin

There total 137 articles about Kobusin 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: 94.0%

Pluviatilol (28115-67-5,52151-92-5,54983-95-8,54983-96-9,62935-82-4,105661-98-1,110268-41-2,111407-29-5,92620-81-0) + methyl iodide (74-88-4) → (1R,2R,5R,6S)-2-(3,4-methylenedioxy)phenyl-6-(3,4-dimethoxy)phenyl-3,7-dioxabicyclo[3.3.0]octane (28115-69-7,31008-19-2,36150-23-9,62839-87-6,63087-37-6,63087-38-7,68296-27-5,128820-38-2,112572-28-8)

Guidance literature:

With caesium carbonate; In acetone; for 18h; Heating;

DOI:10.1021/jo035365r

Reference yield: 88.0%

1-(3,4-methylenedioxyphenyl)-1-(3-(3,4-dimethoxyphenyl)-2-propenyloxy)-2,3-epoxypropane (438581-71-6) → (+/-)-piperitol methyl ether (28115-69-7,31008-19-2,36150-23-9,62839-87-6,63087-37-6,63087-38-7,68296-27-5,112572-28-8,128820-38-2)

Guidance literature:

1-(3,4-methylenedioxyphenyl)-1-(3-(3,4-dimethoxyphenyl)-2-propenyloxy)-2,3-epoxypropane; With bis(cyclopentadienyl)titanium (III) chloride; In tetrahydrofuran; at 20 ℃; for 1h;

With iodine; In tetrahydrofuran;

DOI:10.1055/s-2001-16041

Reference yield: 75.3%

methyl thiomethylpluviatilol (97141-84-9) → (+)-Epipinoresinol (28115-69-7,31008-19-2,36150-23-9,62839-87-6,63087-37-6,63087-38-7,68296-27-5,112572-28-8,128820-38-2)

Guidance literature:

With nickel; In tetrahydrofuran; ethanol; for 4h; Heating;

upstream raw materials:

diazomethane

Pluviatilol

methyl iodide

4-methanesulfonyloxy-3-methoxybenzaldehyde

Refernces

• 1、 Inai, Makoto,Ishikawa, Ryo,Yoshida, Naoto,Shirakawa, Nana,Akao, Yusuke,Kawabe, Yusuke,Asakawa, Tomohiro,Egi, Masahiro,Hamashima, Yoshitaka,Kan, Toshiyuki. "Stereocontrolled total syntheses of optically active furofuran lignans". . p. 3513 - 3521. Retrieved 2015/11/17.
• 2、 Swain, Nigel A.,Brown, Richard C. D.,Bruton, Gordon. "A Versatile Stereoselective Synthesis of endo,exo-Furofuranones: Application to the Enantioselective Synthesis of Furofuran Lignans". . p. 122 - 129. Retrieved 2007/10/03.