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SML2581

Sigma-Aldrich

Silychristin

Milk Thistle component, ≥95% (HPLC)

Synonym(s):

Silychristin, (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, Silymarin II, silichristin

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About This Item

Empirical Formula (Hill Notation):
C25H22O10
CAS Number:
Molecular Weight:
482.44
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥95% (HPLC)

form

solid

solubility

ethanol: 5 mg/mL

storage temp.

2-8°C

SMILES string

COc1cc(ccc1O)[C@@H]2Oc3c(O)cc(cc3[C@H]2CO)[C@H]4Oc5cc(O)cc(O)c5C(=O)[C@@H]4O

InChI

1S/C25H22O10/c1-33-18-6-10(2-3-15(18)28)23-14(9-26)13-4-11(5-17(30)25(13)35-23)24-22(32)21(31)20-16(29)7-12(27)8-19(20)34-24/h2-8,14,22-24,26-30,32H,9H2,1H3/t14-,22+,23+,24-/m1/s1

InChI key

BMLIIPOXVWESJG-LMBCONBSSA-N

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General description

Silychristin is one of 3 flavonolignan isomers in Silymarin mixture, isolated from the fruits of Silybum Sarianum, also known as milk thistle. Silymarin is one of the most widely used phytochemicals due to its extensive therapeutic properties in ancient and modern times. Its hepatoprotective properties is very well established. It is known that Silymarin is an antioxidant and reduces free radical production. It inhibits toxin binding to hepatocytes and was shown to reduce liver injury caused by various agents such as acetaminophen, mycotoxins, bacterial toxins, alcohol and more. Various studies demonstrated protective effects of silymarin not only against hepatotoxic agents but also against nephrotoxic, cardiotoxic and neurotoxic agents. Furthermore, Silymarin was found to inhibit ROS formation and to protect pancreatic β-cells from oxidative stress mediated destruction. An inhibitory effect of silychristin (10-100μM) on the arachidonic acid metabolism by cyclooxygenase (COX) in blood platelets was discovered. This suggests Silychristin can serve as an antiplatelet and anti-inflammatory agent. Interestingly, Silychristin was also found to inhibit the thyroid hormone transporter (MCT8) with IC50 of approximately 100 nM in MDCK1 cells. This data indicate that Silychristin could block the uptake of thyroid hormone.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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