Isolariciresinol (6CI); (+)-Cyclolariciresinol; (+)-Isolariciresinol; Isolariciresinol, (+)-;-Conidendryl alcohol

Base Information

• Chemical Name: Isolariciresinol (6CI); (+)-Cyclolariciresinol; (+)-Isolariciresinol; Isolariciresinol, (+)-;-Conidendryl alcohol
• CAS No.: 5234-71-9
• Molecular Formula: C₂₀H₂₄O₆
• Molecular Weight: 360.407
• Nikkaji Number: J304.422J
• Wikidata: Q104193341
• Mol file: 5234-71-9.mol

Synonyms:Compound NP-007732;SCHEMBL10034083;Isolariciresinol (6CI);(+)-Cyclolariciresinol;(+)-Isolariciresinol;Isolariciresinol, (+)-;-Conidendryl alcohol;ZINC00689725;AKOS040739446;NCGC00385293-01;4-(3-Methoxy-4-hydroxyphenyl)-6-hydroxy-7-methoxy-1,2,3,4-tetrahydronaphthalene-2,3-bismethanol

Chemical Property of Isolariciresinol (6CI); (+)-Cyclolariciresinol; (+)-Isolariciresinol; Isolariciresinol, (+)-;-Conidendryl alcohol

Chemical Property:

• 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:

95% ^*data from raw 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

Technology Process of Isolariciresinol (6CI); (+)-Cyclolariciresinol; (+)-Isolariciresinol; Isolariciresinol, (+)-;-Conidendryl alcohol

There total 30 articles about Isolariciresinol (6CI); (+)-Cyclolariciresinol; (+)-Isolariciresinol; Isolariciresinol, (+)-;-Conidendryl alcohol 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:

7-ethoxy-1-(4-ethoxy-3-methoxy-phenyl)-2,3-bis-hydroxymethyl-6-methoxy-1,2,3,4-tetrahydro-naphthalene

4-(4-Hydroxy-3-methoxy-phenyl)-7-methoxy-1,3,3a,4,9,9a-hexahydro-naphtho[2,3-c]furan-6-ol

2-methoxy-phenol

6-Methoxy-1-(3-methoxy-4-trimethylsilanyloxy-phenyl)-7-trimethylsilanyloxy-2,3-bis-trimethylsilanyloxymethyl-1,2,3,4-tetrahydro-naphthalene

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.