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I1286

Sigma-Aldrich

Icariin

≥94% (HPLC)

Synonym(s):

4′-O-methyl-8-γ,γ-dimethylallylkaempferol-3-rhamnoside-7-glucoside

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About This Item

Empirical Formula (Hill Notation):
C33H40O15
CAS Number:
489-32-7
Molecular Weight:
676.66
MDL number:
MFCD00210516
UNSPSC Code:
12352205
PubChem Substance ID:
329815347
NACRES:
NA.25

Quality Level

100

Assay

≥94% (HPLC)

color

light yellow to yellow

solubility

DMSO: 50 mg/mL, clear, colorless to dark yellow

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

room temp

SMILES string

COc1ccc(cc1)C2=C(O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)C(=O)c4c(O)cc(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)c(C\C=C(\C)C)c4O2

InChI

1S/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1

InChI key

TZJALUIVHRYQQB-XLRXWWTNSA-N

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General description

Icariin is a prenylated flavonol and the major bioactive compound found in Epimedium herb.

Application

Icariin has been used:
  • in the preparation of topical treatment to determine its effects on the improvement of cutaneous wound healing in rats
  • to test its analgesic effects on lower back pain (LBP) in rats
  • as a potential treatment in osteoporosis condition in rats
  • to study its effects on palmitate (PA)-induced insulin resistance in skeletal muscle C2C12 myotubes
  • as a neuroprotective agent to study its effects on amyloid-β (Aβ)-induced neuronal insulin resistance in human neuroblastoma SK-N-MC cells

Biochem/physiol Actions

Icariin is a potent neuroprotective agent in neurodegenerative disorders and other disorders affecting the nervous system. It elicits anti-aging properties in unfertilized oocytes against age-related damage. Icariin exerts anti-inflammatory and antifibrotic properties aiding protection in chronic kidney disease (CKD)-associated renal fibrosis in mouse model. It also serves as an excellent antidiabetic and anti-atherosclerotic agent. Icariin is an excellent anti-cancer agent.
Flavonoid glucoside derived from the the Epimedium plant genus. This pharmacologically active constituent or its derivatives have been shown to enhance bone formation, modulate multidrug resistance, enhance neuronal viability, stimulate angiogenesis, and exhibit antioxidant activity.

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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Qian Qian et al.
Journal of pharmaceutical and biomedical analysis, 66, 392-398 (2012-04-24)
In this work, the metabolite profiles of icariin in rat plasma were qualitatively investigated, and the possible metabolic pathways of icariin were subsequently proposed. After oral administration of icariin, rat plasma samples were collected and pretreated by protein precipitation. Then
D Li et al.
Osteoarthritis and cartilage, 20(12), 1647-1656 (2012-08-25)
To investigate whether icariin, which is a widely used pharmacological constituent in traditional Chinese herbal medicine, can be a potential promoting compound for cartilage tissue engineering. Icariin was added into cell-hydrogel constructs derived from neonatal rabbit chondrocytes and collagen type
Hsin-An Chen et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 59, 152917-152917 (2019-04-13)
The pathology change of renal tubulointerstitial fibrosis is a critical feature of chronic kidney disease (CKD), regardless of the primary insults. The infiltration of inflammatory cells and the consecutive secretion of profibrotic factors are frequently and conspicuously observed during the
Bin Wu et al.
Journal of ethnopharmacology, 142(3), 746-753 (2012-06-13)
Icariin represents an important active component in Herba Epimedii, which is a famous Chinese herbal medicine that is widely used to treat some age-related diseases in oriental countries. The aim of this work was to investigate the effects of icariin
Dawei Zhang et al.
Biochimie, 94(12), 2514-2522 (2012-07-17)
Accumulating evidences suggest that Herba epimedii has the potential benefits against osteoporosis. However, previous studies were focused on the crude extract, total flavonoids (TF) and icariin (ICA), and the detailed molecular mechanisms of action and structure-activity relationship (SAR) remain unclear.
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