Schisandrin B

Base Information

• Chemical Name: Schisandrin B
• CAS No.: 61281-37-6
• Molecular Formula: C₂₃H₂₈O₆
• Molecular Weight: 400.472
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID60976772
• Nikkaji Number: J431.365H
• Wikidata: Q72507130
• Metabolomics Workbench ID: 137890
• ChEMBL ID: CHEMBL479488
• Mol file: 61281-37-6.mol

Synonyms:(+--)-gamma-schizandrin;(-)-gomisin N;Benzo(3,4)cycloocta(1,2-f)(1,3)benzodioxole, 5,6,7,8-tetrahydro-1,2,3,13-tetramethoxy-6,7-dimethyl-, (6R,7S,13aR)-;benzo(3,4)cycloocta(1,2-F)(1,3)benzodioxole, 5,6,7,8-tetrahydro-1,2,3,13-tetramethoxy-6,7-dimethyl-, (6R,7S,13AS)-;gamma-schizandrin;gomisin N;schisandrin B;schizandrin B;wuweizisu b

Chemical Property of Schisandrin B

Chemical Property:

• Vapor Pressure: 2.22E-11mmHg at 25°C
• Refractive Index: 1.543
• Boiling Point: 545 °C at 760 mmHg
• Flash Point: 220.4 °C
• PSA: 55.38000
• Density: 1.148 g/cm³
• LogP: 4.48750
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 400.18858861
• Heavy Atom Count: 29
• Complexity: 544

Purity/Quality:

Schisandrin B ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2=CC3=C(C(=C2C4=C(C(=C(C=C4CC1C)OC)OC)OC)OC)OCO3
• Uses: A compound shown to up-regulate cellular antioxidant response. Schizandrin B is a dibenzocyclooctadiene deriv. isolated from Schisandra chinensis and used commonly in traditional Chinese medicine for the treatment of hepatitis and myocardial disorders.

Technology Process of Schisandrin B

There total 23 articles about Schisandrin B 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: 80.0%

kadsuralignan L → gomisin N (61281-37-6,66211-88-9,69176-52-9,82467-51-4,82467-52-5,82467-53-6,82467-54-7,64121-95-5)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride; In diethyl ether; for 3h; Ambient temperature;

DOI:10.1016/0031-9422(94)00557-A

Reference yield: 59.0%

ananolignan D → gomisin N (61281-37-6,66211-88-9,69176-52-9,82467-51-4,82467-52-5,82467-53-6,82467-54-7,64121-95-5)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride; In diethyl ether; for 3h; Ambient temperature;

DOI:10.1016/0031-9422(94)00557-A

Reference yield:

isofraxetin 6-O-β-D-glucopyranoside → Indole-3-carboxaldehyde (487-89-8,1228547-52-1) + 5,6-dihydroxy-7-methoxycoumarin (50656-75-2) + 2-nonyl-4-hydroxyquinoline N-oxide (55396-45-7) + isofraxidin (486-21-5) + 4,4'-dianisylmethane (726-18-1) + 2,4'-dimethoxydiphenylmethane (30567-87-4) + 1-(6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (22248-13-1) + 2,4-bis(methoxycarbonylamino)toluene (6935-99-5) + toluene-2,6-bis(methyl) carbamate (20913-18-2) + 8'-dehydroxymethyl cleomiscosin A + Benzeneacetamide (103-81-1) + gomisin N (61281-37-6,66211-88-9,69176-52-9,82467-51-4,82467-52-5,82467-53-6,82467-54-7,64121-95-5) + uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) + (+)-isoschizandrin + 6-methoxy-5′′-demethoxydaphneticin

Guidance literature:

With Angelica sinensis (Oliv_.) Diels callus; In methanol; for 168h;

DOI:10.1016/j.bmcl.2016.11.069

upstream raw materials:

3-methoxy-4,5-methylenedioxybenzaldehyde

(R)-dihydro-4-(3,4,5-trimethoxybenzyl)furan-2(3H)-one

(R)-(E)-3-(3,4,5-trimethoxybenzyl)-2-(3,4-methylenedioxy-5-methoxy)butyrolactone

(+/-)-gomisin M₁

Downstream raw materials:

gomisin N

(+)-γ-schizandrin

(-)-deoxyschizandrin

Refernces

• 1、 Tanaka, Masahide,Ohshima, Toshihiro,Mitsuhashi, Hiroshi,Maruno, Masao,Wakamatsu, Takeshi. "Total Syntheses of the Lignans Isolated from Schisandra Chinensis". . p. 11693 - 11702. Retrieved 2007/10/02.
• 2、 Tanaka, Masahide,Ohshima, Toshihiro,Mitsuhashi, Hiroshi,Maruno, Masao,Wakamatsu, Takeshi. "THE FIRST TOTAL SYNTHESIS OF γ-SCHIZANDRIN AND GOMISIN N HAVING NATURAL CONFIGURATIONS". . p. 739 - 742. Retrieved 2007/10/02.