Eudesmin

Base Information

• Chemical Name: Eudesmin
• CAS No.: 526-06-7
• Molecular Formula: C₂₂H₂₆O₆
• Molecular Weight: 386.445
• European Community (EC) Number: 637-069-7
• NSC Number: 674053,404535,35476
• Nikkaji Number: J1.978.720F
• Mol file: 526-06-7.mol

Synonyms:eudesmin

Chemical Property of Eudesmin

Chemical Property:

• Vapor Pressure: 2.72E-10mmHg at 25°C
• Melting Point: 108.5-109.5℃
• Boiling Point: 517.3°Cat760mmHg
• Flash Point: 209.8°C
• PSA: 55.38000
• Density: 1.173g/cm³
• LogP: 3.79620
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 386.17293854
• Heavy Atom Count: 28
• Complexity: 457

Purity/Quality:

≥98% ^*data from raw suppliers

Pinoresinol Dimethyl Ether ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)OC)OC)OC
• Description: Cineole can be obtained by extraction from natural plants, such as Umbelliferae, Rutaceae, Aurelianaceae, Magnoliaceae, Daphneaceae.
• Uses: Eudesmin is used in the bioguided isolation identification and activity evaluation of antifungal compounds from Acorus tatarinowii Schott.

Technology Process of Eudesmin

There total 37 articles about Eudesmin 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: 90.0%

1-(3,4-dimethoxyphenyl)-1-(3-(3,4-dimethoxyphenyl)-2-propenyloxy)-2,3-epoxypropane (438581-68-1) → (+/-)-dimethylpinoresinol (526-06-7,4375-03-5,16499-02-8,25305-05-9,29106-36-3,38609-26-6,38759-91-0,60102-89-8)

Guidance literature:

1-(3,4-dimethoxyphenyl)-1-(3-(3,4-dimethoxyphenyl)-2-propenyloxy)-2,3-epoxypropane; With [Cp₂TiCl]; In tetrahydrofuran; at 60 ℃;

With iodine; In tetrahydrofuran; at 60 ℃; Further stages.;

DOI:10.1021/jo010857u

Reference yield: 55.0%

(3S,3aS,6S,6aS)-3,6-Bis-(3,4-dimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1,4-diol (911858-80-5) → eudesmin (526-06-7,4375-03-5,16499-02-8,25305-05-9,29106-36-3,38609-26-6,38759-91-0,60102-89-8)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1016/j.tetlet.2006.06.127

Reference yield: 51.0%

(3R,3aR,6R,6aR)-3,6-Bis-(3,4-dimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1,4-diol → eudesmine (526-06-7,4375-03-5,16499-02-8,25305-05-9,29106-36-3,38609-26-6,38759-91-0,60102-89-8)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1016/j.tetlet.2006.06.127

upstream raw materials:

dimethyl sulfate

pinoresinol

diazomethane

pinoresinol

Downstream raw materials:

tetrahydro-2-(3,4-dimethoxyphenyl)-4-<(3,4-dimethoxyphenyl)methyl>-3-furanmethanol

pinoresinol

(+)-pinoresinol monomethyl ether

isolariciresinol dimethyl ether

Refernces

• 1、 Kise, Naoki,Fujimoto, Azumi,Moriyama, Noriaki,Ueda, Nasuo. "Stereoselective intramolecular coupling of diaroylacetates of (1R,1′R)-exo,exo′-3,3′-biisoborneol by oxidation with Br 2". . p. 2495 - 2497. Retrieved 2007/10/03.
• 2、 Roy, Subhas Chandra,Rana, Kalyan Kumar,Guin, Chandrani. "Short and stereoselective total synthesis of furano lignans (±)-dihydrosesamin, (±)-lariciresinol dimethyl ether, (±)-acuminatin methyl ether, (±)-sanshodiol methyl ether, (±)-lariciresinol, (±)-acuminatin, and (±)-lariciresinol". . p. 3242 - 3248. Retrieved 2007/10/03.