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SML0551

Sigma-Aldrich

Icaritin

≥98% (HPLC)

Synonym(s):

3,5,7-Trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one

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About This Item

Empirical Formula (Hill Notation):
C21H20O6
CAS Number:
118525-40-9
Molecular Weight:
368.38
MDL number:
MFCD22422519
UNSPSC Code:
12352200
PubChem Substance ID:
329825547
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

light yellow to dark yellow

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

COc1ccc(cc1)C2=C(O)C(=O)c3c(O)cc(O)c(C\C=C(\C)C)c3O2

InChI

1S/C21H20O6/c1-11(2)4-9-14-15(22)10-16(23)17-18(24)19(25)20(27-21(14)17)12-5-7-13(26-3)8-6-12/h4-8,10,22-23,25H,9H2,1-3H3

InChI key

TUUXBSASAQJECY-UHFFFAOYSA-N

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Biochem/physiol Actions

Icaritin is a component of Epimedium flavonoid isolated from Herba Epimedii, which enhances osteoblastic differentiation of mesenchymal stem cells (MSCs) while it inhibits adipogenic differentiation of MSCs by inhibiting PPAR-g pathway. Icaritin has no effect on MSCs proliferation. Also, icaritin potently inhibits chronic myeloid leukemia (CML) and breast cancer cells proliferation most likely by modulation of MAPK/ERK/JNK and JAK2/STAT3 /AKT signaling. As other flavonoids, icaritin may exert estrogen-like activities.
Icaritin enhances osteoblastic differentiation of mesenchymal stem cells (MSCs). It may have estrogen-like activities.

Features and Benefits

This compound is featured on the JAKs, MAPKs and Nuclear Receptors (PPARs) pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Dong Yao et al.
PloS one, 7(8), e41264-e41264 (2012-09-07)
We found that Icaritin, an intestinal metabolite of Epimedium-derived flavonoids (EF) enhanced osteoblastic differentiation of mesenchymal stem cells (MSCs) only under osteogenic induction conditions. We also demonstrated its effect on inhibition of adipogenic differentiation of MSCs. Unlike the findings of
Hongchao Li et al.
Journal of cellular biochemistry (2018-11-06)
Glioblastoma (GBM) is a common and aggressive brain tumor that is associated with significant increase in glycolysis for energy production. Icaritin is a natural compound and exhibits anticancer activity in GBM. However, the effect of icaritin on glycolysis in GBM
Jing-Shan Tong et al.
PloS one, 6(3), e16781-e16781 (2011-03-17)
Icaritin, a compound from Epimedium Genus, has selective estrogen receptor (ER) modulating activities, and possess anti-tumor activity. Here, we examined icaritin effect on cell growth of human endometrial cancer Hec1A cells and found that icaritin potently inhibited proliferation of Hec1A
Jian feng Zhu et al.
PloS one, 6(8), e23720-e23720 (2011-09-03)
To explore the effects of Icaritin on chronic myeloid leukemia (CML) cells and underlying mechanisms. CML cells were incubated with various concentration of Icaritin for 48 hours, the cell proliferation was analyzed by MTT and the apoptosis was assessed with
Wing Pui Tsang et al.
Scientific reports, 7, 40894-40894 (2017-01-17)
Utilization of small molecules in modulation of stem cell self-renewal is a promising approach to expand stem cells for regenerative therapy. Here, we identify Icaritin, a phytoestrogen molecule enhances self-renewal of mouse embryonic stem cells (mESCs). Icaritin increases mESCs proliferation
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