Icariin

Icariin
Names
IUPAC name
7-(β-D-Glucopyranosyloxy)-5-hydroxy-4′-methoxy-8-(3-methylbut-2-en-1-yl)-3-(α-L-rhamnopyranosyloxy)flavone
Preferred 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
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.107.649
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PubChem CID
UNII
InChI
  • 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 checkY
    Key: TZJALUIVHRYQQB-XLRXWWTNSA-N checkY
  • InChI=1/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
    Key: TZJALUIVHRYQQB-XLRXWWTNBA
SMILES
  • O=C3C(\O[C@@H]1O[C@H]([C@H](O)[C@@H](O)[C@H]1O)C)=C(/Oc4c(c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc(O)c34)C\C=C(/C)C)c5ccc(OC)cc5
Properties
Chemical formula
 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).
☒N verify (what is checkY☒N ?)
Infobox references

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. ↑ Liu JJ, Li SP, Wang YT (2006). "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. doi:10.1016/j.chroma.2005.11.036. PMID 16337210.
  2. ↑ Cai WJ, Huang JH, Zhang SQ, Wu B, Kapahi P, Zhang XM, Shen ZY (2011). Blagosklonny MV (ed.). "Icariin and its derivative icariside II extend healthspan via insulin/IGF-1 pathway in C. elegans". PLOS ONE. 6 (12): e28835. Bibcode:2011PLoSO...628835C. doi:10.1371/journal.pone.0028835. PMC 3244416. PMID 22216122.
  3. ↑ Makarova MN, Pozharitskaya ON, Shikov AN, Tesakova SV, Makarov VG, Tikhonov VP (2007). "Effect of lipid-based suspension of Epimedium koreanum Nakai extract on sexual behavior in rats". J Ethnopharmacol. 114 (3): 412–416. doi:10.1016/j.jep.2007.08.021. PMID 17890032.
  4. ↑ "Horny Goat Weed". Drugs.com. August 5, 2019. Retrieved November 7, 2019.
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