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

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

Uses

Used in Traditional Chinese Medicine:
Schizandrin B is used as a therapeutic agent for the treatment of hepatitis and myocardial disorders. Its application in traditional Chinese medicine is based on its ability to alleviate symptoms and improve the overall health of patients suffering from these conditions.
Used in Antioxidant Applications:
Schizandrin B is used as an antioxidant agent to up-regulate cellular antioxidant response. This property makes it a valuable compound in the development of treatments for various diseases and conditions associated with oxidative stress.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Schizandrin B is used as a key ingredient in the development of drugs targeting hepatitis and myocardial disorders. Its incorporation into drug formulations is due to its proven efficacy in traditional Chinese medicine and its antioxidant properties.
Used in Nutraceutical Industry:
Schizandrin B can also be used in the nutraceutical industry as a supplement to promote overall health and well-being. Its antioxidant properties and traditional use in Chinese medicine make it an attractive option for consumers seeking natural remedies to support their health.

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

• 5780-07-4 3-methoxy-4,5-methylenedioxybenzaldehyde 
• 82425-43-2 (+/-)-gomisin M₁ 
• 77-78-1 dimethyl sulfate 
• 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 
• 82425-45-4 (+)-gomisin M₂ 
• 82425-44-3 (-)-gomisin L₂ 
• 82425-43-2 (-)-gomisin L₁ 
• 58546-54-6 gomisin A 
• 62555-46-8 C₂₃H₂₆O₆ 
• 161906-44-1 (R)-(E)-3-(3,4,5-trimethoxybenzyl)-2-(3,4-methylenedioxy-5-methoxy)butyrolactone 
• 76763-88-7 (R)-dihydro-4-(3,4,5-trimethoxybenzyl)furan-2(3H)-one 
• 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 FIRST TOTAL SYNTHESIS OF γ-SCHIZANDRIN AND GOMISIN N HAVING NATURAL CONFIGURATIONS

The total syntheses of γ-schizandrin and gomisin N were achieved in a stereoselective manner.The success of these synthesis heavily depends on the stereoselective reduction of tetracyclic lactones with magnesium in methanol.