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61301-33-5

13,14-dimethoxy-6,7-dimethyl-5,6,7,8-tetrahydro[1,3]benzodioxolo[5',6':3,4]cycloocta[1,2-f][1,3]benzodioxole (non-preferred name)

CAS: 61301-33-5

Molecular Formula: C22H24O6

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61301-33-5 - Names and Identifiers

Name 13,14-dimethoxy-6,7-dimethyl-5,6,7,8-tetrahydro[1,3]benzodioxolo[5',6':3,4]cycloocta[1,2-f][1,3]benzodioxole (non-preferred name)
Synonyms WUWEIZISU C
,8-dimethyl-
Schizandrin C
Schisandrin C
SCHIZANDRIN C
(S)-(-)-Schisandrin C
Schisandrin C (Schizandrin-C
Schisandrin C (S)-(-)-Schisandrin C
CAS 61301-33-5
InChI InChI=1/C22H24O6/c1-11-5-13-7-15-19(27-9-25-15)21(23-3)17(13)18-14(6-12(11)2)8-16-20(22(18)24-4)28-10-26-16/h7-8,11-12H,5-6,9-10H2,1-4H3

61301-33-5 - Physico-chemical Properties

Molecular FormulaC22H24O6
Molar Mass384.42
Density1.232
Melting Point122-123℃
Boling Point549.2±50.0 °C(Predicted)
Specific Rotation(α)-54.9°(c1.0,chloroform),-31.4°(c0.587,chloroform)
Flash Point226.7°C
Solubility Soluble in ethyl acetate, acetone, chloroform, methanol, etc.
Vapor Presure1.5E-11mmHg at 25°C
AppearanceColorless flake crystal
Storage Condition2-8℃
Refractive Index1.572
MDLMFCD00272170
Physical and Chemical PropertiesColorless crystal, soluble in methanol, ethanol, DMSO and other organic solvents, derived from Schisandra chinensis.
In vitro study Schisandrin C (25-100 μM; 48 hours) down-regulates expression levels of Bcl-2, Bcl-xL and a concomitant degradation of poly(ADP-ribose) polymerase (PARP). It also activates caspase-3 and -9 in U937 cells.Schisandrin C (25-100 μM; 48 hours) induces apoptosis in a dose-dependent manner. And the fragmentation of genomic DNA is also increased in U937 cells.Schisandrin C (25-100 μM; 72 hours) induces G1 arrest, it down-regulates cyclin D1, cyclin E, cyclin-dependent kinase (Cdk) 4 and E2Fs expression, and also exhibits inhibition of pRB, and up-regulation of the Cdk inhibitor p21(WAF1/CIP1). Western Blot Analysis Cell Line: U937 cells Concentration: 25 μM,50 μM,100 μM Incubation Time: 48 hours Result: Decreased the expression of apoptosis related proteins. Apoptosis Analysis Cell Line: U937 cells Concentration: 25 μM,50 μM,100 μM Incubation Time: 48 hours Result: Induced cell apoptosis. Cell Cycle Analysis Cell Line: U937 cells Concentration: 25 μM,50 μM,100 μM Incubation Time: 48 hours Result: Induced growth inhibition and G1 arrest of U937 cells.
In vivo study Schisandrin C (lateral ventricle injection (i.c.v.); 15-150 μg/kg; 5 days) reduces Aβ1-42-induced memory deficits in the Y-maze test. Neurons in the hippocampus of SCH-C (15 μg/kg)-treated group returned to normal level, and and SCH-C group (150 μg/kg) has slight neuroprotective effects Aβ1-42-induced group. SCH-C (15 μg/kg) recoveres the activities of SOD and GSHPx and the ratios of GSH, decreases the levels of ChEtotal in the brain of the Aβ1–42-induced amnesic mice simultaneously. Animal Model: Aβ1-42-induced Alzheimer’s disease mice Dosage: 15-150 μg/kg Administration: Lateral ventricle injection (i.c.v.); 15-150 μg/kg; 5 days Result: Exhibited potent neuroprotective effects linking to anti-ChEtotal activities and anti-oxidative mechanisms in Aβ1-42-induced amnestic mice.

61301-33-5 - Reference

Reference
Show more
1. Cheng Zhenyu, Yang Yingjie, Liu Zhigang, et al. Comprehensive extraction method of main effective components from schisandra chinensis [J]. Jiangsu Agricultural Sciences 2014 42(006):273-276.
2. Wu Hao, Shan-Zhang, lunar November, Yu Xiaojing et al. Simultaneous determination of five lignans in schisandra chinensis from different habitats by HPLC [J]. Chinese national and folk medicine 2018 v.27;No.322(05):13-17.
3. Zhu Jingbo, Li, Wenyu, Xiao, Wei et al. Preparation of lignans in schisandra chinensis by two-dimensional reversed-phase liquid chromatography [J]. Chromatogram 2018 036(005):464-473.
4. Dai Hui, Suhang, Cai Pengfei, et al. Changes of color and eight lignans of schisandra vinegar before and after steaming [J]. Chinese patent medicine 2019 41(05):1091-1096.
5. Soviet Union Lin, Li Min, Xu Min, etc. Predictive analysis of quality markers of schisandra chinensis before and after processing with vinegar based on multivariate statistical analysis and network pharmacology [J]. Chinese Herbal Medicine, 2015, Volume 50, Issue 19, pages 4643-4653, ISTIC PKU CSCD CA, 2019.
6. Wang Guoli wishes Hong, Yan, Lin, Hai, et al. Simultaneous determination of six lignans in schisandra chinensis by Reversed-phase high performance liquid chromatography [J]. Journal of Food Safety and quality testing 2014 000(008):2470-2475.
7. Jin Miao, Liu Jinna, Liu Hui, Black Yu Rong, Liu Yulan. Effects of different processing methods on lignans of introduced schisandra chinensis in Shaanxi [J]. Shaanxi Agricultural Sciences, 2020,66(11):17-20.
8. Jiao Meiyu, Yu-yue, Wu Haoxian, Kang Tingguo, Zhang Hui. Study on the mechanism and qualitative recognition model of "color discrimination and qualitative analysis" of schisandra chinensis [J]. China Pharmacy, 2020,31(24):3007-3012.
9. [IF = 6.079] Hongyan Zhu et al."Data and hypnotic effects of supercritical carbon reagent fluid extraction from Schisandra chinensis in mice." J Food Drug Anal. 2016 Oct;24:831
10. [IF = 3.935] Yunlong Guo et al."Rapid characterization of Schisandra species by using direct analysis in real time mass spectrometry."J Pharmaceut Biomed. 2021 Jan;192:113648
11. [IF=3.205] Xiaorong Hou et al."Development of an immobilized liposome chromatography method for screening and characterizing α-glucosidase-binding compounds."J Chromatogr B. 2020 Jul;1148:122097
12. [IF=3] Qu Lala et al."Phenotypic assessment and ligand screening of ETA/ETB receptors with label-free dynamic mass redistribution assay."N-S Arch Pharmacol. 2020 Jun;393(6):937-950
13. [IF=1.618] Song Haiyan et al."Matrix Solid-Phase Dispersion Coupled with HPLC-UV for Simultaneous Extraction, Purification and Determination of Six Lignans in Schisandra chinensis Fruits."J Chromatogr Sci. 2021 Jun;:
14. [IF=4.36] Zhenghua Wu et al."Schisandrol A the main active ingredient of Schisandrae Chinensis Fructus, inhibits pulmonary fibrosis through suppression of the TGF-β signaling pathway as revealed by UPLC-Q-TOF/MS, network pharmacology and experimental verification.

61301-33-5 - Reference Information

biological activity Schisandrin C (Schizandrin-C) is a phytochemical lignan isolated from schisandra chinensis. Schisandrin C has a variety of biological activities, including anticancer, anti-inflammatory and antioxidant effects. Schisandrin C can be used in the study of cancer, Alzheimer's disease, liver disease. Schisandrin C induces apoptosis.
in vitro study Schisandrin C (25-100 μm; 48 hours) down-regulations expression levels of Bcl-2, bcl-xL and a concomitant degradation of poly(ADP-ribose) polymer (PARP). It also activates caspase-3 and -9 in U937 cells.Schisandrin C (25-100 μm; 48 hours) induces apoptosis in a dose-dependent manner. And the fragmentation of genomic DNA is also increased in U937 cells.Schisandrin C (25-100 μM; 72 hours) induces G1 arrest, it down-regulates cyclin D1, cyclin E, cyclin-dependent kinase (Cdk) 4 and E2Fs expression, and also exhibits inhibition of pRB and up-regulation of the Cdk inhibitor p21(WAF1/CIP1). Western Blot Analysis Cell Line: U937 cells Concentration: 25 μM,50 μM,100 μM Incubation Time: 48 hours Result: Decreased the expression of apoptosis related proteins. Apoptosis Analysis Cell Line: U937 cells Concentration: 25 μM,50 μM,100 μM Incubation Time: 48 hours Result: Induced cell apoptosis. Cell Cycle Analysis Cell Line: U937 cells Concentration: 25 μM,50 μM,100 μM Incubation Time: 48 hours Result: Induced growth inhibition and G1 arrest of U937 cells.
Cell Line: U937 cells
U937 cells
U937 cells
Concentration: 25 μM,50 μM,100 μM
25 μM,50 μM,100 μM
25 μM,50 μM,100 μM
Incubation Time: 48 hours
48 hours
48 hours
Result: Decreased the expression of apoptosis related proteins.
Induced cell apoptosis.
Induced growth inhibition and G1 arrest of U937 cells.
Exhibited potent neuroprotective effects linking to anti-ChEtotal activities and anti-oxidative mechanisms in Aβ1-42-induced amnestic mice.
in vivo studies Schisandrin C (lateral ventricle injection (I. c.v.); 15-150 μg/kg; 5 days) reduced Aβ1-42-induced memory failures in the Y-maze test. Neurons in the hippocampus of SCH-C (15 μg/kg)-treated group returned to normal level, and and SCH-C group (150 μg/kg) has light neuroprotection effects a beta 1-42-induced group. SCH-C (15 μg/kg) recoveres the activities of SOD and GSHPx and the ratios of GSH, decreases the levels of ChEtotal in the brain of the Aβ1-42-induced amnesic mice simultaneously. Animal Model: Aβ1-42-induced Alzheimer's disease mice Dosage: 15-150 μg/kg Administration: Lateral ventricle injection (I .c.v.); 15-150 μg/kg; 5 days Result: Exhibited potent neuroprotective effects linking to anti-ChEtotal activities and anti-oxidative mechanisms in Aβ1-42-induced amnestic mice.
Animal Model: Aβ1-42-induced Alzheimer’s disease mice
Dosage: 15-150 μg/kg
Administration: Lateral ventricle injection (i.c.v.); 15-150 μg/kg; 5 days
Chemical properties colorless crystals, soluble in methanol, ethanol, DMSO and other organic solvents, derived from schisandra chinensis.
Use schisandrin C has antagonistic, anti-cancer, anti-ulcer, liver protection effect.
Last Update:2024-04-10 22:29:15
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61301-33-5
2-METHYL-2-PHENYLPROPANENITRILE
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