Icariin

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Not to be confused with Icaridin.

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Icariin
Icariin.svg
Names
IUPAC name
5-Hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-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]oxychromen-4-one
Identifiers
489-32-7
ChEBI CHEBI:78420 N
ChEMBL ChEMBL553204 YesY
ChemSpider 4477421 YesY
Jmol 3D model Interactive image
PubChem 5318997
  • 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 YesY
    Key: TZJALUIVHRYQQB-XLRXWWTNSA-N YesY
  • 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
  • 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
C33H40O15
Molar mass 676.67 g·mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Icariin is a chemical compound classified as a 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 plants belonging to the genus Epimedium which are commonly known as Horny Goat Weed or Yin Yang Huo.[1] Extracts from these plants are reputed to produce aphrodisiac effects, and are used in traditional Chinese medicine to enhance erectile function.[2]

It is thought that icariin is an active component of Epimedium extracts, as it has been shown to share several mechanisms of action with compounds used in Western medicine to treat impotence. In particular, icariin is a weak PDE5 inhibitor in vitro[3][4][5] and to enhance the production of nitric oxide,[6] as well as mimicking the effects of testosterone in rats.[7][unreliable medical source?] It is a weak antioxidant[8][9] and has antidepressant-like effects in mice.[10][11][12] It also has neuroprotective effects in rats.[13][14]

References

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  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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