61281-37-6

Basic information

• Product Name: SCHIZANDRIN B
• Synonyms: 6,7-dimethyl-, stereoisomer;Benzo [3,4] cycloocta [1,2-f][1,3]benzodioxole;5,6,7,8-Tetrahydro-1,10,11,12-tetramethoxy-6,7-dimethyl-2,3-(methylenedioxy)dibenzo[a,c]cyclooctene;5,6,7,8-Tetrahydro-1,2,3,13-tetramethoxy-6,7-dimethylbenzo[3,4]cycloocta[1,2-f][1,3]benzodioxole;5,6,7,8-Tetrahydro-6,7-dimethyl-1,2,3,13-tetramethoxybenzo[3,4]cycloocta[1,2-f][1,3]benzodioxole;Schizandrin B, froM Schisandra chinensls;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)-rel-;Schisandrin B (Sch B)
• CAS NO: 61281-37-6
• Molecular Formula: C₂₃H₂₈O₆
• Molecular Weight: 400.46
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;Miscellaneous Natural Products
• Mol File: 61281-37-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 545 °C at 760 mmHg
• Flash Point: 220.4 °C
• Appearance: /
• Density: 1.148 g/cm³
• Vapor Pressure: 2.22E-11mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: SCHIZANDRIN B(CAS DataBase Reference)
• NIST Chemistry Reference: SCHIZANDRIN B(61281-37-6)
• EPA Substance Registry System: SCHIZANDRIN B(61281-37-6)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 61281-37-6(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Different sources of media describe the Uses of 61281-37-6 differently. You can refer to the following data:
1. A compound shown to up-regulate cellular antioxidant response.
2. 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.

Definition

ChEBI: An organic heterotetracyclic compound that is found in Fructus Schisandrae and Schisandra chinensis.

InChI:InChI=1/C23H28O6/c1-12-7-14-9-16(24-3)20(25-4)22(26-5)18(14)19-15(8-13(12)2)10-17-21(23(19)27-6)29-11-28-17/h9-10,12-13H,7-8,11H2,1-6H3/t12-,13+/m0/s1

Upstream product

• 76763-88-7 (R)-dihydro-4-(3,4,5-trimethoxybenzyl)furan-2(3H)-one 
• 58546-54-6 gomisin A 
• 62555-46-8 C₂₃H₂₆O₆ 
• 82425-43-2 (-)-gomisin L₁ 
• 77-78-1 dimethyl sulfate 
• 82425-44-3 (-)-gomisin L₂ 
• 82425-45-4 (+)-gomisin M₂ 
• 148812-34-4 (3aRS,SR-Biar)-3a,4-dihydro-8,9,10,11-tetramethoxy-6,7-(methylenedioxy)dibenzo<4,5:6,7>cycloocta<1,2-c>furan-1(3H)-one 
• 82425-43-2 (+/-)-gomisin M₁ 
• 161906-44-1 (R)-(E)-3-(3,4,5-trimethoxybenzyl)-2-(3,4-methylenedioxy-5-methoxy)butyrolactone 
• 5780-07-4 3-methoxy-4,5-methylenedioxybenzaldehyde 
• 82425-46-5 C₂₄H₂₈O₇ 

Downstream Products

• 64121-95-5 gomisin N 
• 64121-95-5 (+)-γ-schizandrin 
• 61281-38-7 (-)-deoxyschizandrin 

Relevant articles and documents

Biotransformation of isofraxetin-6-O-β-D-glucopyranoside by Angelica sinensis (Oliv.) Diels callus

Isofraxetin-6-O-β-D-glucopyranoside, identified from traditional medicinal herbal Xanthoceras sorbifolia Bunge, has been demonstrated to be a natural neuroinflammatory inhibitor. In order to obtain more derivatives with potential anti-neuroinflammatory effects, biotransformation was carried out. According to the characteristics of coumarin skeleton, suspension cultures of Angelica sinensis (Oliv.) Diels callus (A. sinensis callus) were employed because of the presence of diverse phenylpropanoids biosynthetic enzymes. As a result, 15 products were yielded from the suspension cultures, including a new coumarin: 8′-dehydroxymethyl cleomiscosin A (1), together with 14 known compounds. Their structures were elucidated by extensive spectroscopic analysis. Furthermore, the biotransformed pathways were discussed. Among them, compound 13 was transformed from isofraxetin-6-O-β-D-glucopyranoside, while compounds 1–6, 10–12, 14–15 were derived from the culture medium stimulated by the substrate. The biotransformation processes include hydroxylation, oxidation and esterification. Furthermore, their inhibitory effects on lipopolysaccharide (LPS)-activated nitric oxide (NO) production were evaluated in BV2 microglial cells. It is worth noting that, 1, 1′-methanediylbis(4-methoxybenzene) (3), obtucarbamates A (5), 2-nonyl-4-hydroxyquinoline N-oxide (10) and 1H-indole-3-carbaldehyde (11) exhibited significant inhibitory effect against neuroinflammation with IC50values at 1.22, 10.57, 1.02 and 0.76?μM respectively, much stronger than that of the positive control minocycline (IC5035.82?μM).

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.

The constituents of Schizandra chinensis BAILL. X. The structures of γ-schizandrin and four new lignans, (-)-gomisins L1 and L2, (±)-gomisin M1 and (+)-gomisin M2

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