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Chemical Structure| 802918-57-6 Chemical Structure| 802918-57-6

Structure of Silybin
CAS No.: 802918-57-6

Chemical Structure| 802918-57-6

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Silybin is a flavonolignan isolated from the seeds of milk thistle (Silybum marianum). Silybin induces apoptosis and possesses hepatoprotective, antioxidant, anti-inflammatory, and anticancer activities.

Synonyms: Silibinin

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Product Details of Silybin

CAS No. :802918-57-6
Formula : C25H22O10
M.W : 482.44
SMILES Code : O=C1[C@@H]([C@H](OC2=CC(O)=CC(O)=C12)C3=CC=C4OC(C(OC4=C3)C5=CC=C(C(OC)=C5)O)CO)O
Synonyms :
Silibinin
MDL No. :MFCD00872186

Safety of Silybin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
HepG2 cells 2, 10, 50 µM 24 hours To evaluate the effect of silybin on P450s activity under TG-induced ER stress. Results showed that silybin at medium and low concentrations ameliorated P450s activity, while high concentration may inhibit P450s activity. Acta Pharmacol Sin. 2023 Jan;44(1):133-144.
LX-2 cells 20 μg/mL 24 hours Evaluate the inhibitory effect of SLB nanosuspension on collagen I secretion, results showed NS-SLB and NS-SLB-HC significantly inhibited collagen I secretion Int J Nanomedicine. 2023 Sep 12;18:5197-5211.
3T3-L1 adipocytes 30 µM or 80 µM 24 hours To evaluate the effect of Silybin on TNFα secretion and glucose uptake. Silybin 80 µM as post-treatment or pre-treatment decreased TNFα levels, improving glucose uptake, but the glucose uptake enhancement did not depend on GLUT4 protein expression. Adipocyte. 2024 Dec;13(1):2374062
SKOV3 cells 100 µM 24 hours Silybin inhibits mitochondrial oxidative phosphorylation and the PPP pathway. Cancer Sci. 2022 Sep;113(9):3032-3043.
OVCAR3 cells 50 µM and 100 µM 24 hours and 48 hours Silybin inhibits cell proliferation and induces apoptosis by increasing ROS levels. Cancer Sci. 2022 Sep;113(9):3032-3043.
SCC (Huh7:LX2 coculture) 5-7.5 µM 24, 96, 144 hours To assess the effect of Silybin on cell viability and collagen deposition in the coculture model. Silybin showed no toxic effects and significantly reduced FFA-induced collagen deposition (40% reduction, 5 µM Silybin). Molecules. 2019 Apr 2;24(7):1280
Huh7 cells 5-7.5 µM 24, 96, 144 hours To assess the effect of Silybin on Huh7 cell viability and proliferation. Silybin significantly reduced cell viability at the highest concentration after 144 h (≈22%). FFA treatment did not significantly affect Huh7 cell viability, but the combination of FFA + Silybin showed deleterious effects at 96 and 144 h. Molecules. 2019 Apr 2;24(7):1280
LX2 cells 5-7.5 µM 24, 96, 144 hours To assess the effect of Silybin on LX2 cell viability and proliferation. Silybin significantly reduced cell viability at the highest concentration after 144 h (≈18%). FFA treatment increased LX2 cell proliferation, which was partially reversed by Silybin. Molecules. 2019 Apr 2;24(7):1280
HeLa 10 µM and 50 µM 48 hours Evaluation of antiproliferative activity, results showed inhibition of proliferation at 10 µM and 50 µM Molecules. 2022 Mar 5;27(5):1702
WM266 10 µM and 50 µM 48 hours Evaluation of antiproliferative activity, results showed inhibition of proliferation at 10 µM and 50 µM Molecules. 2022 Mar 5;27(5):1702
A375 10 µM and 50 µM 48 hours Evaluation of antiproliferative activity, results showed inhibition of proliferation at 10 µM and 50 µM Molecules. 2022 Mar 5;27(5):1702
Jurkat 10 µM and 50 µM 48 hours Evaluation of antiproliferative activity, results showed a reduction in proliferation of about 20% at 10 µM and more than 40% at 50 µM Molecules. 2022 Mar 5;27(5):1702
RAW 264.7 cells 1.0 μg/mL to 50 μg/mL 48 hours Evaluate the cytotoxicity of SLB nanosuspension, results showed SLB exhibited low toxicity against RAW 264.7 cells at concentrations up to 50 μg/mL Int J Nanomedicine. 2023 Sep 12;18:5197-5211.
LO2 cells 1.0 μg/mL to 50 μg/mL 48 hours Evaluate the cytotoxicity of SLB nanosuspension, results showed SLB exhibited low toxicity against LO2 cells at concentrations up to 50 μg/mL Int J Nanomedicine. 2023 Sep 12;18:5197-5211.
HepG2 cells 1.0 μg/mL to 50 μg/mL 48 hours Evaluate the cytotoxicity of SLB nanosuspension, results showed SLB exhibited low toxicity against HepG2 cells at concentrations up to 50 μg/mL Int J Nanomedicine. 2023 Sep 12;18:5197-5211.
HepG2 cells 68 µM 48 hours To evaluate the effect of Silybin on BPA-induced lipid peroxidation. Results showed that Silybin significantly reduced BPA-induced lipid peroxidation. Sci Rep. 2019 Mar 1;9(1):3228
HepG2 cells 68 µM 48 hours To evaluate the effect of Silybin on BPA-induced proliferation in HepG2 cells. Results showed that Silybin significantly counteracted BPA-induced cell proliferation. Sci Rep. 2019 Mar 1;9(1):3228
HepG2 cells 68 µM 72 hours Silybin induced growth inhibition by increasing nitric oxide (NO) production and MnSOD activity, reducing lipid peroxidation, blocking HepG2 cells in the G1 phase of the cell cycle and activating apoptosis. Additionally, silybin increased ceramide synthesis and modulated miRNA secretion, specifically upregulating miR223-3p and miR16-5p, and downregulating miR-92-3p. Int J Mol Sci. 2019 May 3;20(9):2190.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
BALB/c nude mice Ovarian cancer xenograft model Oral gavage 100 mg/kg Once daily for 6 weeks Silybin suppresses tumor growth of ovarian cancer cells via oral administration. Cancer Sci. 2022 Sep;113(9):3032-3043.
Male C57BL/6J mice MPTP-induced Parkinson's disease model Oral 100, 200, 300, 400, 500 mg/kg Once daily for 5 consecutive days To evaluate the neuroprotective effects of silybin in the MPTP-induced Parkinson's disease model. Results showed that oral administration of silybin at 100 mg/kg preserved about 60% of dopamine levels, improved motor deficits, preserved neurotrophic factors content and mitochondrial function, reduced lipid peroxidation, diminished proinflammatory cytokines to basal levels, enhanced fractalkine production in the striatum and substantia nigra, and increased IL-10 and IL-4 levels in the substantia nigra in MPTP mice. Mol Neurobiol. 2023 Dec;60(12):6774-6788
C57BL/6 mice High-fat-diet induced nonalcoholic fatty liver disease model Intragastric administration 50, 100 mg/kg/day Once daily for 4 weeks To investigate the effect of silybin on P450s activity in HFD-induced NAFLD mice. Results showed that silybin dose-dependently reversed the inhibition of P450s activity by HFD. Acta Pharmacol Sin. 2023 Jan;44(1):133-144.
Kunming mice CCl4-induced hepatic fibrosis model and bile duct ligation (BDL)-induced hepatic fibrosis model Tail vein injection 8 mg/kg SLB Twice a week, treatment lasted for 2 to 3 weeks Evaluate the therapeutic effect of SLB nanosuspension on hepatic fibrosis, results showed NS-SLB and NS-SLB-HC significantly alleviated hepatic fibrosis, reduced ALT and AST levels, and inhibited the expression of α-SMA and collagen I Int J Nanomedicine. 2023 Sep 12;18:5197-5211.

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT03538327 Hypertension PHASE4 COMPLETED 2025-05-14 -
NCT00915681 Amatoxin Poisoning|Amanita Poi... More >>soning|Mushroom Poisoning|Liver Failure Less << PHASE2 TERMINATED 2020-04-10 Recruitment Hot Line for the U... More >>nited States, Somerset, New Jersey, 08873, United States|Mylan Specialty LLP, Morgantown, West Virginia, 26504-4310, United States Less <<
NCT01129570 Advanced Hepatocellular Carcin... More >>oma Less << PHASE1 COMPLETED 2025-06-13 Columbia University Medical Ce... More >>nter, New York, New York, 10032, United States Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

2.07mL

0.41mL

0.21mL

10.36mL

2.07mL

1.04mL

20.73mL

4.15mL

2.07mL

 

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