9,9'-Di-O-(E)-feruloylsecoisolariciresinol

Base Information

• Chemical Name: 9,9'-Di-O-(E)-feruloylsecoisolariciresinol
• CAS No.: 56973-66-1
• Molecular Formula: C40H42O12
• Molecular Weight: 714.75400
• DSSTox Substance ID: DTXSID101103789
• Nikkaji Number: J373.425K
• Wikidata: Q105168852
• Metabolomics Workbench ID: 134564
• ChEMBL ID: CHEMBL447988
• Mol file: 56973-66-1.mol

Synonyms:1,4-O-diferuloylsecoisolariciresinol

Chemical Property of 9,9'-Di-O-(E)-feruloylsecoisolariciresinol

Chemical Property:

• PSA: 170.44000
• LogP: 6.07420
• XLogP3: 7.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 19
• Exact Mass: 714.26762677
• Heavy Atom Count: 52
• Complexity: 1040

Purity/Quality:

98%Min ^*data from raw suppliers

Secoisolariciresinoldiferulate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)CC(COC(=O)C=CC2=CC(=C(C=C2)O)OC)C(CC3=CC(=C(C=C3)O)OC)COC(=O)C=CC4=CC(=C(C=C4)O)OC)O
• Isomeric SMILES: COC1=C(C=CC(=C1)C[C@H]([C@H](COC(=O)/C=C/C2=CC(=C(C=C2)O)OC)CC3=CC(=C(C=C3)O)OC)COC(=O)/C=C/C4=CC(=C(C=C4)O)OC)O

Technology Process of 9,9'-Di-O-(E)-feruloylsecoisolariciresinol

There total 9 articles about 9,9'-Di-O-(E)-feruloylsecoisolariciresinol 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: 73.0%

C64H98O12Si4 → (+/-)-9,9'-O-diferuloylsecoisolariciresinol (56973-66-1,133097-13-9,146918-28-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.09.014

Reference yield:

C13H14O6 (111194-03-7) → (+/-)-9,9'-O-diferuloylsecoisolariciresinol (56973-66-1,133097-13-9,146918-28-7)

Guidance literature:

Multi-step reaction with 8 steps

1: sulfuric acid / 24 h / Reflux

2: lithium / methanol / 48 h / Reflux

3: sulfuric acid / 24 h / Reflux

4: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C

5: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C

6: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -15 °C

7: dmap; dicyclohexyl-carbodiimide / dichloromethane / 4 h / 20 °C

8: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere

With 1H-imidazole; dmap; lithium aluminium tetrahydride; sulfuric acid; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; lithium; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 2: Stobbe reaction;

DOI:10.1016/j.bmcl.2011.09.014

Reference yield:

C14H16O6 (190004-89-8) → (+/-)-9,9'-O-diferuloylsecoisolariciresinol (56973-66-1,133097-13-9,146918-28-7)

Guidance literature:

Multi-step reaction with 7 steps

1: lithium / methanol / 48 h / Reflux

2: sulfuric acid / 24 h / Reflux

3: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C

4: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C

5: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -15 °C

6: dmap; dicyclohexyl-carbodiimide / dichloromethane / 4 h / 20 °C

7: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere

With 1H-imidazole; dmap; lithium aluminium tetrahydride; sulfuric acid; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; lithium; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Stobbe reaction;

DOI:10.1016/j.bmcl.2011.09.014

upstream raw materials:

C₁₃H₁₄O₆

C₁₄H₁₆O₆

C₂₁H₂₀O₈

C₂₂H₂₂O₈

Refernces