61281-38-7

Basic information

• Product Name: Schisandrin A
• Synonyms: dibenzo(a,c)cyclooctene,5,6,7,8-tetrahydro-6,7-dimethyl-1,2,3,10,11,12-hexamet;R(+) DEOXYSCHISANDRIN A;R(+) DEOXYSCHIZANDRIN A;R(+) SCHISANDRIN A;R(+) SCHIZANDRIN A;SCHIZANDRIN A;SCHISANDRIN A;WUWEIZISU A
• CAS NO: 61281-38-7
• Molecular Formula: C22H28O6
• Molecular Weight: 388.45
• Product Categories: Miscellaneous Natural Products;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 61281-38-7.mol
• Article Data: 13

Chemical Properties

• Melting Point: 116-117 °C
• Boiling Point: 544.2 °C at 760 mmHg
• Flash Point: 215.6 °C
• Appearance: White powder
• Density: 1.08 g/cm³
• Vapor Pressure: 2.39E-11mmHg at 25°C
• Refractive Index: 1.519
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Schisandrin A(CAS DataBase Reference)
• NIST Chemistry Reference: Schisandrin A(61281-38-7)
• EPA Substance Registry System: Schisandrin A(61281-38-7)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: HP1595000
• Hazardous Substances Data: 61281-38-7(Hazardous Substances Data)

Usage

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.

Chemical Properties

White powder

Uses

Schizandrin A is an extract from Schisandra chinesis. a dibenzocyclooctadiene lignan with antiinflammatory activity.

InChI:InChI=1/C24H32O6/c1-13-9-15-11-17(25-3)21(27-5)23(29-7)19(15)20-16(10-14(13)2)12-18(26-4)22(28-6)24(20)30-8/h11-14H,9-10H2,1-8H3/t13-,14+

Upstream product

• 66280-25-9 (-)-gomisin J 
• 77-78-1 dimethyl sulfate 
• 487-11-6 elemicin 
• 137255-18-6 (-)-grandisin 
• 65171-10-0 (+/-)-4-(3,4,5-trimethoxyphenyl)-4,5-dihydro-2(3H)-furanone 
• 68196-50-9 1,2,3,10,11,12-hexamethoxy-6,7-dimethyl-5,6-dihydrodibenzo[a,c]cyclooctene 
• 7432-28-2 schizandrin 
• 61281-37-6 gomisin N 
• 110397-81-4 (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 
• 110397-83-6 (M*,6R*,7R*)-5,6,7,8-tetrahydro-1,2,3,10,11,12-hexamethoxy-6,7-bis(hydroxymethyl)-dibenzocyclooctene 
• 93395-16-5 (3R*,4R*)-3-(3,4,5-trimethoxybenzyl)-4-(3,4,5-trimethoxybenzyl)-4,5-dihydro-2(3H)-furanone 
• 21852-50-6 3,4,5-trimethoxybenzyl bromide 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 317806-14-7 1,2,3-trimethoxy-5-(2-nitro-propenyl)benzene 

Downstream Products

• 66280-25-9 (-)-gomisin J 

Relevant articles and documents

Total Syntheses of the Lignans Isolated from Schisandra Chinensis

The total syntheses of wuweizisu C (4), gomisin J (6), gomisin N (7), and γ-schizandrin (8) having natural configuration were accomplished in a stereoselective manner.The catalytic hydrogenation or the metal mediated 1,4-reduction of the tetracyclic lactones (12, 17, 22, 30) played the significant role for the stereoselective introduction of C6, C7 dimethyl moiety.Furthermore, the neighboring carbonyl group assisted regioselective demethylation of 5 was essential for the synthesis of 6.

Ruthenium dioxide in fluoro acid medium V. Application to the non phenolic oxidative coupling of diarylbutanes. Conformational studies of cis and trans deoxyschizandrins

Ruthenium (IV) dioxide dihydrate in fluoro acidic medium was found to be a very efficient agent for the non phenolic oxidative coupling of diarylbutanes. We observed along with the expected aryl-aryl coupling, an unusual aryl-benzyl coupling, leading to a known class of lignans, the aryltetralins. Conformational studies of resultant cis and trans deoxyschizandrins were performed using high resolution NMR and molecular models.

Ruthenium dioxide in fluoro acid medium: I. A new agent in the biaryl oxidative coupling. Application to the synthesis of non phenolic bisbenzocyclooctadiene lignan lactones

Ruthenium (IV) dioxide dihydrate in fluoro acid medium was found to be a very efficient agent for the oxidative coupling of non phenolic lignans and their derivatives, and this method was applied to the total synthesis of (+/-)-neoisostegane 2a and (+/-)-steganolide A 2b. This procedure was also used to obtain the first stereospecific synthesis of a cis-bisbenzocyclooctadiene lactone, the (+/-)-deoxyschizandrin 17, of which, was afforded by a short reduction sequence.