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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
Pricing and availability is not currently available.

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.[1]

Application

Icariin has been used:
  • in the preparation of topical treatment to determine its effects on the improvement of cutaneous wound healing in rats[2]
  • to test its analgesic effects on lower back pain (LBP) in rats[3]
  • as a potential treatment in osteoporosis condition in rats[4]
  • to study its effects on palmitate (PA)-induced insulin resistance in skeletal muscle C2C12 myotubes[5]
  • as a neuroprotective agent to study its effects on amyloid-β (Aβ)-induced neuronal insulin resistance in human neuroblastoma SK-N-MC cells[6]

Biochem/physiol Actions

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.
Icariin is a potent neuroprotective agent in neurodegenerative disorders and other disorders affecting the nervous system.[1] It elicits anti-aging properties in unfertilized oocytes against age-related damage.[7] Icariin exerts anti-inflammatory and antifibrotic properties aiding protection in chronic kidney disease (CKD)-associated renal fibrosis in mouse model.[8] It also serves as an excellent antidiabetic[9] and anti-atherosclerotic agent.[10] Icariin is an excellent anti-cancer agent.[1]

Storage Class Code

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
WXBF3544V
WXBF2114V
WXBD8605V
WXBD2828V
MKCJ1712

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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
Feifei Tao et al.
Biochemical pharmacology, 85(6), 798-807 (2012-12-25)
Inflammatory bowel disease (IBD) is a chronic inflammatory disorder in the intestine which involves overproduction of pro-inflammatory cytokines and excessive functions of inflammatory cells. However, current treatments for IBD may have potential adverse effects including steroid dependence, infections and lymphoma.
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
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.
Da Hye Kim et al.
Molecules (Basel, Switzerland), 22(6) (2017-06-14)
The therapeutic properties of Epimediumkoreanum are presumed to be due to the flavonoid component icariin, which has been reported to have broad pharmacological potential and has demonstrated anti-diabetic, anti-Alzheimer's disease, anti-tumor, and hepatoprotective activities. Considering these therapeutic properties of icariin
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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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