Chemistry:Icariin

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Icariin
Icariin.svg
Names
IUPAC name
7-(β-D-Glucopyranosyloxy)-5-hydroxy-4′-methoxy-8-(3-methylbut-2-en-1-yl)-3-(α-L-rhamnopyranosyloxy)flavone
Systematic IUPAC name
5-Hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-1-benzopyran-4-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
Properties
C33H40O15
Molar mass 676.668 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Tracking categories (test):

Icariin is a chemical compound classified as a prenylated flavonol glycoside, a type of flavonoid. It is the 8-prenyl derivative of kaempferol 3,7-O-diglucoside. The compound has been isolated from several species of plant belonging to the genus Epimedium which are commonly known as horny goat weed, Yin Yang Huo,[1] and Herba epimedii.[2] Extracts from these plants are reputed to produce aphrodisiac effects, and are used in traditional Chinese medicine to enhance erectile function.[3] However, clinical trial data are lacking to support these claims.[4]

References

  1. "Optimization for quantitative determination of four flavonoids in Epimedium by capillary zone electrophoresis coupled with diode array detection using central composite design". J Chromatogr A 1103 (2): 344–349. 2006. doi:10.1016/j.chroma.2005.11.036. PMID 16337210. 
  2. "Icariin and its derivative icariside II extend healthspan via insulin/IGF-1 pathway in C. elegans". PLOS ONE 6 (12): e28835. 2011. doi:10.1371/journal.pone.0028835. PMID 22216122. Bibcode2011PLoSO...628835C. 
  3. "Effect of lipid-based suspension of Epimedium koreanum Nakai extract on sexual behavior in rats". J Ethnopharmacol 114 (3): 412–416. 2007. doi:10.1016/j.jep.2007.08.021. PMID 17890032. 
  4. "Horny Goat Weed". August 5, 2019. https://www.drugs.com/npp/horny-goat-weed.html.