Silibinin

Available from stock

Silibinin

SKU
S0276

Category:

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
22888-70-6
CAS-Number
C25H22O10
Molecular Formula
482.44
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

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

Documentation

Safety Data Sheet (SDS)
CDX S0276 SDS.pdf
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
Description
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.
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
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

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.

SKU: S0276 Category:

Additional information

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
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

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