Deoxyschizandrin

Base Information

• Chemical Name: Deoxyschizandrin
• CAS No.: 61281-38-7
• Molecular Formula: C₂₄H₃₂O₆
• Molecular Weight: 416.514
• Hs Code.: 29093090
• DSSTox Substance ID: DTXSID20976773
• Nikkaji Number: J527.345E
• Wikipedia: Deoxyschizandrin
• Wikidata: Q27149861
• Metabolomics Workbench ID: 137956
• ChEMBL ID: CHEMBL479898
• Mol file: 61281-38-7.mol

Synonyms:deoxyschisandrin;deoxyschizandrin;schisandrin A;schizandrin A

Chemical Property of Deoxyschizandrin

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 2.39E-11mmHg at 25°C
• Melting Point: 116-117 °C
• Refractive Index: 1.519
• Boiling Point: 544.2 °C at 760 mmHg
• Flash Point: 215.6 °C
• PSA: 55.38000
• Density: 1.08 g/cm³
• LogP: 4.28400
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 416.21988874
• Heavy Atom Count: 30
• Complexity: 484

Purity/Quality:

99%, ^*data from raw suppliers

SchizandrinA ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2=CC(=C(C(=C2C3=C(C(=C(C=C3CC1C)OC)OC)OC)OC)OC)OC
• Description: Schisandrin A is a lignan that has been found in Schisandra and has diverse biological activities. It binds to adiponectin receptor 2 (IC50 = 3.2 μM). Schisandrin A (10, 20, and 50 μM) reduces LPS-induced production of nitric oxide (NO), IL-6, and TNF-α and apoptosis in primary mouse microglial cells. It reverses P-glycoprotein-mediated doxorubicin resistance in MCF-7/dox cells when used at a concentration of 20 μM. Schisandrin A (4, 12, and 36 mg/kg) reverses short-term and spatial memory deficits, as well as decreases in cerebral superoxide dismutase (SOD) and glutathione peroxidase (GPX) activities induced by amyloid β (1-42) (Aβ42; ) in a mouse model of Alzheimer’s disease.
• Uses: Schizandrin A is an extract from Schisandra chinesis. a dibenzocyclooctadiene lignan with antiinflammatory activity.

Technology Process of Deoxyschizandrin

There total 46 articles about Deoxyschizandrin 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: 56.0%

5,5'-(2,3-dimethylbutane-1,4-diyl)bis(1,2,3-trimethoxybenzene) (50544-08-6,72730-20-2,75597-96-5,115587-61-6,107191-91-3) → (+/-)-deoxyschizandrin (61281-38-7,63598-55-0,63640-13-1,69176-53-0,101757-58-8,114488-89-0,115587-63-8,115587-64-9,157087-43-9,157087-44-0)

Guidance literature:

With vanadium(V) oxytrifluoride; trifluoroacetic acid; In dichloromethane; 1) -78 deg C, 30 min, 2) room temperature, 30 min;

Reference yield: 56.0%

5,5'-(2,3-dimethylbutane-1,4-diyl)bis(1,2,3-trimethoxybenzene) (50544-08-6,72730-20-2,75597-96-5,115587-61-6,107191-91-3) → (+/-)-deoxyschizandrin (61281-38-7,63598-55-0,63640-13-1,69176-53-0,101757-58-8,114488-89-0,115587-63-8,115587-64-9,157087-43-9,157087-44-0)

Guidance literature:

With vanadium(V) oxytrifluoride; trifluoroacetic acid; In dichloromethane; 1) -78 deg C, 30 min, 2) room temperature, 30 min;

Reference yield:

elemicin (487-11-6) → (+/-)-deoxyschizandrin (61281-38-7,63598-55-0,63640-13-1,69176-53-0,101757-58-8,114488-89-0,115587-63-8,115587-64-9,157087-43-9,157087-44-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / HBr / acetic acid / 3 h / 0 °C

2: 1) Mg, 2) (E)-2-t-butyl-3-phenyloxaziridine / 1) THF, 0 deg C, 2) 0 deg C, 15 h

3: 56 percent / trifluoroacetic acid, VOF₃ / CH₂Cl₂ / 1) -78 deg C, 30 min, 2) room temperature, 30 min

With 2-tert-butyl-3-phenyloxaziridine; vanadium(V) oxytrifluoride; hydrogen bromide; magnesium; trifluoroacetic acid; In dichloromethane; acetic acid;

upstream raw materials:

(-)-gomisin J

dimethyl sulfate

(3aR,S-Biar)-3a,4-dihydro-6,7,8,9,10,11-hexamethoxydibenzo<4,5:6,7>cycloocta<1,2-c>furan-1(3H)-one

gomisin N

Downstream raw materials:

(-)-gomisin J

Refernces

• 1、 Dhal,Landais,Lebrun,Lenain,Robin. "Ruthenium dioxide in fluoro acid medium V. Application to the non phenolic oxidative coupling of diarylbutanes. Conformational studies of cis and trans deoxyschizandrins". . p. 1153 - 1164. Retrieved 2007/10/02.
• 2、 Carroll, Anthony R.,Read, Roger W.,Taylor, Walter C.. "Intramolecular Oxidative Coupling of Aromatic Compounds. VII. A Convenient Synthesis of (+/-)-Deoxyschizandrin". . p. 1579 - 1590. Retrieved 2007/10/02.