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Merck
CN

SML2383

Isosilybin

≥98% (HPLC)

Synonym(s):

Isosilybin, mixture of isomers, (2R,3R)-2-[2,3-Dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one, Isosilybinin

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About This Item

Empirical Formula (Hill Notation):
C25H22O10
CAS Number:
72581-71-6
Molecular Weight:
482.44
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD09842608

Key Documents

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SMILES string

O1C(C(Oc3c1cc(cc3)C4Oc5c(c(cc(c5)O)O)C(=O)C4O)c2cc(c(cc2)O)OC)CO

InChI

1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-18-7-12(3-5-16(18)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

InChI key

FDQAOULAVFHKBX-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

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Biochem/physiol Actions

Isosilybin is a diastereoisomeric mixture of flavonolignans isosilybin A and isosilybin B isolated from milk thistle (Silybum marianum) that exhibits hepatoprotective activity. Isosilybin potently inhibits Cytochrome P4502C8 (CYP2C8) activity in human liver microsomes. Also Isosilybin is an activator of PPARγ.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000045296
0000062546
0000063308
0000055822
0000055823

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Eva-Maria Pferschy-Wenzig et al.
Journal of natural products, 77(4), 842-847 (2014-03-07)
Peroxisome proliferator-activated receptor gamma (PPARγ) is a key regulator of glucose and lipid metabolism. Agonists of this nuclear receptor are used in the treatment of type 2 diabetes and are also studied as a potential treatment of other metabolic diseases
Ahmed A Albassam et al.
Chemico-biological interactions, 271, 24-29 (2017-05-02)
Milk thistle is a widely-consumed botanical used for an array of purported health benefits. The primary extract of milk thistle is termed silymarin, a complex mixture that contains a number of structurally-related flavonolignans, the flavonoid, taxifolin, and a number of
David Y-W Lee et al.
Journal of natural products, 66(9), 1171-1174 (2003-09-27)
Two pairs of diastereoisomeric flavonolignans, silybin A, silybin B, isosilybin A, and isosilybin B, were successfully separated from Silybum marianum by sequential silica gel column chromatography, preparative reversed-phase HPLC, and recrystallization. Complete stereochemical assignments at C-2, C-3, C-7', and C-8'

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