Specifications
- Purity
- ≥98% (HPLC)
- Appearance
- White to slightly yellow powder
- Identity
- 1H-NMR
Properties
- Solvents
- DMSO (10 mg/ml), DMF (20 mg/ml)
- Melting Point
- 167° C
Category: Phytochemicals
Silibinin is a naturally occurring flavanone from Silybum marianum (milk thistle plant) and the main component (active principle) of the Silymarin extract. Silibinin has shown pleiotropic biological properties, including potent antioxidant, anti-inflammatory, anticancer, antidiabetic, hepatoprotective, neuroprotective, antiviral, antimicrobial and immunosuppressive activities. Silibinin demonstrates promising anticancer effects in vitro and in vivo. The molecular mechanisms of silibinin-mediated antiproliferative effects are mainly via receptor tyrosine kinases, androgen receptor, STATs, NF-&kappa,B, cell cycle arrest and apoptotis/autophagy inducing signaling pathways in various cancer cells. Silibinin was reported to improve glycemic homeostasis by improving the activity of pancreatic β,-cells, increasing insulin sensitivity of liver and muscle cells and decreasing lipid deposition in adipocytes. Next to modulating the NF&kappa, signaling pathway, Sibilin also inhibits NLRP1/NLRP3 inflammasomes signaling pathways. It modulates many molecular changes caused by xenobiotics and ultraviolet radiation to protect the skin and is used in cosmeceutical preparations.
Synonyms | 2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-6-(3,5,7-trihydroxy-4-oxobenzopyran-2-yl)benzodioxin, Silybin, NSC 651520, Flavobin, Silymarin I |
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Purity | ≥98% (HPLC) |
Appearance | White to slightly yellow powder |
CAS-Number | 22888-70-6 |
Molecular Formula | C25H22O10 |
Molecular Weight | 482.44 |
Identity | 1H-NMR |
Solvents | DMSO (10 mg/ml), DMF (20 mg/ml) |
Melting Point | 167° C |
Smiles | OC1=C2C(O[C@@H](C3=CC=C(O[C@@H](CO)[C@H](C4=CC=C(O)C(OC)=C4)O5)C5=C3)[C@H](O)C2=O)=CC(O)=C1 |
InChi Key | SEBFKMXJBCUCAI-PQVVKJAFSA-N |
Shipping | AMBIENT |
Short Term Storage | -20°C |
Long Term Storage | -20°C |
Handling Advice | Protect from light and moisture. |
Use / Stability | Stable for at least 2 years after receipt when stored at -20°C. |
Hazard statements | H302, H410 |
Precautionary statements | P264, P270, P273, P301 + P312, P330, P391, P501 |
GHS Symbol | GHS07+GHS09 |
Signal word | Warning |
Transportation | Not dangerous goods |
References | (1) C. Dehmlow, et al., Life Sci. 58, 1591 (1996), (2) C. Dehmlow, et al., Hepatology 23, 749 (1996), (3) J.A. Hannay & D. Yu, Cancer Biol. Ther. 2, 532 (2003), (4) R.P. Singh & R. Agarwal, Mutat. Res. 555, 21 (2004) (Review), (5) R.P. Singh, et al., Oncogene 24, 1188 (2005), (6) K. Min, et al., Arch. Pharm. Res. 30, 1265 (2007), (7) R.P. Singh & R. Agarwal, Clin. Dermatol. 27, 479 (2009) (Review), (8) L. Li, et al., Expert Opin. Investig. Drugs 19, 243 (2010) (Review), (9) F. Yin, et al., Neurochem. Int. 58, 399 (2011), (10) G. Marrazzo, et al., Neurosci. Lett. 504, 252 (2011), (11) C.O. Souza, et al., Life Sci. 91, 159 (2012), (12) J. McClure, et al., PLoS One 7, e41832 (2012), (13) D.R. de Oliveira, et al., Biomed. Res. Int. 2015, 292797 (2015), (14) N. Polachi, et al., Eur. J. Med. Chem. 123, 577 (2016) (Review), (15) J. Bosch-Barrera, et al., Cancer Treat Rev. 58, 61 (2017) (Review), (16) L. Tian, et al., Microb. Pathog. 108, 104 (2017), (17) R. Faridnia, et al., Ann. Parasitol. 64, 29 (2018), (18) C. Chu, et al., Arch. Pharm. Res. 41, 785 (2018) (Review), (19) Z. Jahanafrooz, et al., Life Sci. 213, 236 (2018) (Review), (20) M.L. Matias, et al., Molecules 24, E1548 (2019) |
InChi | InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23+,24-,25-/m0/s1 |
Quantity | 10 g, 100 g, Bulk |