Silicristin

Names

[ Name ]:
Silicristin

[Synonym ]:
Silicristin
EINECS 251-720-9
Silicristinum
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydrochromen-4-one
Silicristinum [INN-Latin]
Silicristina
(2R,3R)-3,5,7-Trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-4H-chromen-4-one
Silicristina [INN-Spanish]
4H-1-Benzopyran-4-one, 2-[(2R,3S)-2,3-dihydro-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-benzofuranyl]-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-
Silychristin
Silymarin II
Silicristine [INN-French]
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-2,3-dihydrobenzofuran-5-yl]chroman-4-one
Silicristine

Biological Activity

[Description]:

Silychristin is an abundant flavonolignan present in the fruits of Silybum marianum, with antioxidant properties. Silychristin is a potent inhibitor of the thyroid hormone transporter MCT8, and elicits a strong inhibition of T3 uptake with an IC50 of 110 nM[1][2].

[Related Catalog]:

Research Areas >> Endocrinology

Signaling Pathways >> Others >> Others

[References]

[1]. Biedermann D, et al. Silychristin: Skeletal Alterations and Biological Activities. J Nat Prod. 2016 Dec 23;79(12):3086-3092.

[2]. Johannes J, et al. Silychristin, a Flavonolignan Derived From the Milk Thistle, Is a Potent Inhibitor of the Thyroid Hormone Transporter MCT8. Endocrinology. 2016 Apr;157(4):1694-701.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
782.0±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₅H₂₂O₁₀

[ Molecular Weight ]:
482.436

[ Flash Point ]:
270.5±26.4 °C

[ Exact Mass ]:
482.121307

[ PSA ]:
166.14000

[ LogP ]:
2.20

[ Vapour Pressure ]:
0.0±2.8 mmHg at 25°C

[ Index of Refraction ]:
1.716

[ Storage condition ]:
2-8°C

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ Safety Phrases ]:
22-45

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Effect of the flavanolignans of Silybum marianum L. on lipid peroxidation in rat liver microsomes and freshly isolated hepatocytes.

Pharmacol. Res. 25(2) , 147-54, (1992)

The effect of several flavanolignans (silicristin, silidianin, silybin and isosilybin) present in silymarin, the extract of Silybum marianum fruits, was tested on lipid peroxidation in rat liver micro...

Separation and characterization of silybin, isosilybin, silydianin and silychristin in milk thistle extract by liquid chromatography-electrospray tandem mass spectrometry.

J. Chromatogr. A. 1116(1-2) , 57-68, (2006)

A selective and sensitive liquid chromatography/tandem mass spectrometry (LC/MS/MS) method has been developed for the characterization of silymarin in commercially available milk thistle extract. In t...

Identifying the differential effects of silymarin constituents on cell growth and cell cycle regulatory molecules in human prostate cancer cells.

Int. J. Cancer 123(1) , 41-50, (2008)

Prostate cancer (PCa) is the leading cause of cancer-related deaths in men; urgent measures are warranted to lower this deadly malignancy. Silymarin is a known cancer chemopreventive agent, but the re...