CAS 22888-70-6|Silymarin
| Common Name | Silymarin | ||
|---|---|---|---|
| CAS Number | 22888-70-6 | Molecular Weight | 482.436 |
| Density | 1.5±0.1 g/cm3 | Boiling Point | 793.0±60.0 °C at 760 mmHg |
| Molecular Formula | C25H22O10 | Melting Point | 164-174°C |
| MSDS | ChineseUSA | Flash Point | 274.5±26.4 °C |
| Symbol | GHS07 | Signal Word | Warning |
Names
| Name | Silibinin |
|---|---|
| Synonym | More Synonyms |
Silymarin BiologicalActivity
| Description | Silibinin, an effective anti-cancer and chemopreventive agent, has been shown to exert multiple effects on cancer cells, including inhibition of both cell proliferation and migration.IC50 value:Target: anticancerin vitro: silibinin significantly induced the expression of the non-steroidal anti-inflammatory drug-activated gene-1 (NAG-1) in both p53 wild-type and p53-null cancer cell lines, suggesting that silibinin-induced NAG-1 up-regulation is p53-independent manner.Silibinin up-regulates early growth response-1 (EGR-1) expression [1]. silibinin induced cell death in human breast cancer cell lines MCF7 and MDA-MB-231. Silibinininduced cell death was attenuated by antioxidants, N-acetylcysteine (NAC) and Trolox, suggesting that the effect of silibinin was dependent on generation of reactive oxygen species (ROS) [2]. SIL treatment resulted in a dose- and time-dependent inhibition of HCC cell viability, SIL exhibited strong antitumor activity, as evidenced not only by reductions in tumor cell adhesion, migration, intracellular glutathione (GSH) levels and total antioxidant capability (T-AOC) but also by increases in the apoptotic index, caspase3 activity, and reactive oxygen species (ROS). SIL treatment decreased the expression of the Notch1 intracellular domain (NICD), RBP-Jκ, and Hes1 proteins, upregulated the apoptosis pathway-related protein Bax, and downregulated Bcl2, survivin, and cyclin D1. Notch1 siRNA (in vitro) or DAPT (a known Notch1 inhibitor, in vivo) further enhanced the antitumor activity of SIL, and recombinant Jagged1 protein (a known Notch ligand in vitro) attenuated the antitumor activity of SIL [3].in vivo: Topical application of silibinin at the dose of 9 mg/mouse effectively suppressed oxidative stress and deregulated activation of inflammatory mediators and tumorigenesis[4]. The kidney cortex of vehicle-treated control OVE26 mice displayed greater Nox4 expression and twice as much superoxide production than cortex of silybin-treated mice. The glomeruli of control OVE26 mice displayed 35% podocyte drop out that was not present in the silybin-treated mice [5]. |
|---|---|
| Related Catalog | Signaling Pathways >>Autophagy >>AutophagyResearch Areas >>CancerNatural Products >>Flavonoids |
| References | [1]. Woo SM, et al. Silibinin induces apoptosis of HT29 colon carcinoma cells through early growth response-1 (EGR-1)-mediated non-steroidal anti-inflammatory drug-activated gene-1 (NAG-1) up-regulation. Chem Biol Interact. 2014 Jan 16;211C:36-43. [2]. Kim TH, et al. Silibinin induces cell death through ROS-dependent down-regulation of Notch-1/ERK/Akt signaling in human breast cancer cells. J Pharmacol Exp Ther. 2014 Jan 28. [3]. Zhang S, et al. Silybin-mediated inhibition of Notch signaling exerts antitumor activity in human hepatocellular carcinoma cells. PLoS One. 2013 Dec 27;8(12):e83699. [4]. Khan AQ, et al. Silibinin Inhibits Tumor Promotional Triggers and Tumorigenesis Against Chemically Induced Two-Stage Skin Carcinogenesis in Swiss Albino Mice: Possible Role of Oxidative Stress and Inflammation. Nutr Cancer. 2013 Dec 23. [5]. Khazim K, et al. The antioxidant silybin prevents high glucose-induced oxidative stress and podocyte injury in vitro and in vivo. Am J Physiol Renal Physiol. 2013 Sep 1;305(5):F691-700. |
Chemical & Physical Properties
| Density | 1.5±0.1 g/cm3 |
|---|---|
| Boiling Point | 793.0±60.0 °C at 760 mmHg |
| Melting Point | 164-174°C |
| Molecular Formula | C25H22O10 |
| Molecular Weight | 482.436 |
| Flash Point | 274.5±26.4 °C |
| Exact Mass | 482.121307 |
| PSA | 155.14000 |
| LogP | 2.59 |
| Vapour Pressure | 0.0±2.9 mmHg at 25°C |
| Index of Refraction | 1.684 |
| InChIKey | SEBFKMXJBCUCAI-HKTJVKLFSA-N |
| SMILES | COc1cc(C2Oc3cc(C4Oc5cc(O)cc(O)c5C(=O)C4O)ccc3OC2CO)ccc1O |
| Storage condition | −20°C |
| Stability | Stable. Incompatible with strong oxidizing agents, strong bases. |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1056 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23, 1978-88. For publisher information, see ZYZAEU. Volume(issue)/page/year: 18,404,1983
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 300 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23, 1978-88. For publisher information, see ZYZAEU. Volume(issue)/page/year: 18,404,1983
Safety Information
| Symbol | GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H315-H319-H335 |
| Precautionary Statements | P305 + P351 + P338 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
| Hazard Codes | Xi |
| Risk Phrases | R36/37/38 |
| Safety Phrases | S26-S37/39-S24/25-S22 |
| RIDADR | 3172 |
| WGK Germany | 3 |
| RTECS | DJ2981770 |
| HS Code | 2932999099 |
Customs
| HS Code | 2932999099 |
|---|---|
| Summary | 2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
Articles75
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| Effect of silibinin on the pharmacokinetics of nitrendipine in rabbits. Eur. J. Drug Metab. Pharmacokinet. 39(4) , 277-81, (2014) Silibinin, a major constituent of silymarin, is widely used for its hepatoprotective effects. This study investigated the effect of silibinin on the pharmacokinetics of oral nitrendipine in rabbits. I... |
Synonyms
| flavobin |
| (2R,3R)-3,5,7-Trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-chromen-4-one |
| EINECS 245-302-5 |
| SILYBIN A |
| 4H-1-Benzopyran-4-one, 2-[(2R,3R)-2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)- |
| SILYBININ |
| [2R-[2a,3b,6(2R*,3R*)]]-2-[2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one |
| silliver |
| Silibinin |
| Silybin |
| Silybum Substance E6 |
| silybine |
| MFCD00872186 |
| 7c3mt |
| Silymrin |
| Dura-Silymarin |
