Isolariciresinol

Base Information

• Chemical Name: Isolariciresinol
• CAS No.: 548-29-8
• Molecular Formula: C₂₀H₂₄O₆
• Molecular Weight: 360.407
• UNII: FRJ46XRJ28
• DSSTox Substance ID: DTXSID20203273
• Nikkaji Number: J16.950A
• Wikidata: Q27137882
• Metabolomics Workbench ID: 133540
• ChEMBL ID: CHEMBL399512
• Mol file: 548-29-8.mol

Synonyms:1,2,3,4-tetrahydro-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-6-methoxy-2,3-naphthalenedimethanol;isolariciresinol

Chemical Property of Isolariciresinol

Chemical Property:

• Melting Point: 112 °C
• Boiling Point: 584.1±50.0 °C(Predicted)
• PKA: 10.08±0.35(Predicted)
• PSA: 99.38000
• Density: 1.275±0.06 g/cm3(Predicted)
• LogP: 2.02000
• XLogP3: 2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 360.15728848
• Heavy Atom Count: 26
• Complexity: 446

Purity/Quality:

99% ^*data from raw suppliers

(+)-Isolariciresinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(C(C(CC2=C1)CO)CO)C3=CC(=C(C=C3)O)OC)O
• Isomeric SMILES: COC1=C(C=C2[C@@H]([C@H]([C@@H](CC2=C1)CO)CO)C3=CC(=C(C=C3)O)OC)O

Technology Process of Isolariciresinol

There total 25 articles about Isolariciresinol 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: 93.0%

lariciresinol (486-29-3,83327-19-9,105367-81-5,27003-73-2) → (6R,7R,8S)-isolariciresinol (5234-71-9,6753-57-7,110268-37-6,548-29-8)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; methanol; at 45 ℃; for 4h;

DOI:10.1039/b202493d

Reference yield: 81.0%

O-dibenzylisolariciresinol (111266-05-8) → (6R,7R,8S)-isolariciresinol (5234-71-9,6753-57-7,110268-37-6,548-29-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 18h; under 2280 Torr; Ambient temperature;

DOI:10.3987/R-1987-05-1169

Reference yield: 77.0%

(7RS,8R,8'R)-3,3'-dimethoxyligna-4,4',7,9,9'-pentaol → (6R,7R,8S)-isolariciresinol (5234-71-9,6753-57-7,110268-37-6,548-29-8)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; at 50 ℃; for 6h;

DOI:10.1039/b202493d

upstream raw materials:

O-dibenzylisolariciresinol

conidendrin

lariciresinol

3-methoxy-4-(phenylmethoxy)benzaldehyde

Downstream raw materials:

phyltetralin

isolariciresinol dimethyl ether

(+)-Isolariciresinol-monomethylether

(+)-isolariciresinol teraacetate

Refernces

• 1、 Eklund, Patrik,Sillanpaeae, Reijo,Sjoeholm, Rainer. "Synthetic transformation of hydroxymatairesinol from Norway spruce (picea abies) to 7-hydroxysecoisolariciresinol, (+)-lariciresinol and (+)-cyclolariciresinol". . p. 1906 - 1910. Retrieved 2007/10/03.
• 2、 Schoettner, Matthias,Gansser, Dietmar,Spiteller, Gerhard. "Lignans from the roots of Urtica dioica and their metabolites bind to human sex hormone binding globulin (SHBG)". . p. 529 - 532. Retrieved 2007/10/03.