Secoisolariciresinol

Base Information

• Chemical Name: Secoisolariciresinol
• CAS No.: 29388-59-8
• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.423
• Hs Code.: 2909500090
• European Community (EC) Number: 249-599-2
• UNII: M8QRJ7JEJH
• DSSTox Substance ID: DTXSID50183615
• Nikkaji Number: J20.796I
• Wikipedia: Secoisolariciresinol
• Wikidata: Q4413253
• NCI Thesaurus Code: C68495
• Metabolomics Workbench ID: 42480
• ChEMBL ID: CHEMBL368347
• Mol file: 29388-59-8.mol

Synonyms:2,3-bis((4-hydroxy-3-methoxyphenyl)methyl)-1,4-butanediol;knotolan;secoisolariciresinol;secoisolariciresinol, (R*,S*)-isomer

Chemical Property of Secoisolariciresinol

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.09E-15mmHg at 25°C
• Melting Point: 112-114 °C
• Refractive Index: 1.598
• Boiling Point: 609.1 °C at 760 mmHg
• PKA: 9.81±0.20(Predicted)
• Flash Point: 322.1 °C
• PSA: 99.38000
• Density: 1.251 g/cm³
• LogP: 2.11720
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 362.17293854
• Heavy Atom Count: 26
• Complexity: 357

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Secoisolariciresinol ^*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(CO)C(CC2=CC(=C(C=C2)O)OC)CO)O
• Isomeric SMILES: COC1=C(C=CC(=C1)C[C@@H](CO)[C@@H](CC2=CC(=C(C=C2)O)OC)CO)O
• Recent ClinicalTrials: Prevention Strategy for Pre-Menopausal Women at High Risk for Development of Breast Cancer
• Uses: Secoisolariciresinol is a Mongolian folk medicine with anti-myocardial ischemia effects. Possesses anti-oxidant and anti-microbial activity.

Technology Process of Secoisolariciresinol

There total 76 articles about Secoisolariciresinol 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: 100.0%

pinoresinol (4263-88-1,7452-03-1,10061-38-8,18779-41-4,18779-51-6,24404-50-0,81446-29-9,146338-76-3,487-36-5) → (-)-secoisolariciresinol (3688-23-1,57759-55-4,71772-17-3,75365-01-4,145265-02-7,29388-59-8)

Guidance literature:

With hydrogen; palladium(II) hydroxide; In methanol; ethyl acetate; for 3h;

DOI:10.1021/acs.orglett.0c00773

Reference yield: 81.0%

(8R,8'R)-4,4'-dibenzyloxy-3,3'-dimethoxylignane-9,9'-diol (111194-08-2) → (-)-secoisolariciresinol (3688-23-1,57759-55-4,71772-17-3,75365-01-4,145265-02-7,29388-59-8)

Guidance literature:

With 5% Pd/C; hydrogen; In tetrahydrofuran; at 20 ℃; for 6h;

DOI:10.1271/bbb.80461

Reference yield: 51.0%

secoisolariciresinol diglycoside (158932-33-3,257930-74-8) → (-)-secoisolariciresinol (3688-23-1,57759-55-4,71772-17-3,75365-01-4,145265-02-7,29388-59-8)

Guidance literature:

With hydrogenchloride; water; at 20 - 98 ℃; for 28h;

DOI:10.1007/s10600-010-9720-4

upstream raw materials:

(8R,8'R)-4,4'-dibenzyloxy-3,3'-dimethoxylignane-9,9'-diol

(+)-epipinoresinol

pinoresinol

matairesinol

Downstream raw materials:

L_g-threo-1,4-bis-benzoyloxy-2,3-bis-(4-benzoyloxy-3-methoxy-benzyl)-butane

(2R,3R)-2,3-bis[(3,4-dimethoxyphenyl)methyl]butane-1,4-diol

(8R,8'R)-9,9'-epoxy-3,4,3',4'-tetramethoxylignane

(3R,4R)-3,4-bis(4-hydroxy-3-methoxybenzyl)-4-butanolide

Refernces

• 1、 Hanessian, Stephen,Reddy Vakiti, Jithender. "Total Synthesis and Stereochemical Confirmation of (-)-Olivil, (+)-Cycloolivil, (-)-Alashinols F and G, (+)-Cephafortin A, and Their Congeners: Filling in Biosynthetic Gaps". supporting information. p. 3345 - 3350. Retrieved 2020/04/30.
• 2、 -. "Modification method for improving oil solubility of lignan". Paragraph 0048-0051. . Retrieved 2019/10/08.