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Rosavin

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Rosavin
Names
IUPAC name
(2E)-3-phenylprop-2-en-1-yl 6-O-α-L-arabinopyranosyl-α-D-glucopyranoside
Other names
Rosavin; (2S,3R,4S,5S,6R)-2-[(E)-3-phenylprop-2-enoxy]-6-([(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl)oxane-3,4,5-triol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C20H28O10/c21-12-9-28-19(17(25)14(12)22)29-10-13-15(23)16(24)18(26)20(30-13)27-8-4-7-11-5-2-1-3-6-11/h1-7,12-26H,8-10H2/b7-4+/t12-,13+,14-,15+,16-,17+,18+,19-,20+/m0/s1 ☒N
    Key: RINHYCZCUGCZAJ-IPXOVKFZSA-N ☒N
  • InChI=1/C20H28O10/c21-12-9-28-19(17(25)14(12)22)29-10-13-15(23)16(24)18(26)20(30-13)27-8-4-7-11-5-2-1-3-6-11/h1-7,12-26H,8-10H2/b7-4+/t12-,13+,14-,15+,16-,17+,18+,19-,20+/m0/s1
    Key: RINHYCZCUGCZAJ-IPXOVKFZBN
  • O[C@H]3[C@H](OC[C@H]2O[C@@H](OC\C=C\c1ccccc1)[C@H](O)[C@@H](O)[C@@H]2O)OC[C@H](O)[C@@H]3O
Properties
C20H28O10
Molar mass 428.430
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 ?)

Rosavin is a cinnamyl alcohol glycoside found in the plant Rhodiola rosea. It is thought to be one of the compounds responsible for the antidepressant and anxiolytic actions of this plant, along with salidroside.[1][2]

References

  1. ^ Perfumi M, Mattioli L. Adaptogenic and central nervous system effects of single doses of 3% rosavin and 1% salidroside Rhodiola rosea L. extract in mice. Phytotherapy Research. 2007 Jan;21(1):37-43. doi:10.1002/ptr.2013 PMID 17072830
  2. ^ Mattioli L, Funari C, Perfumi M. Effects of Rhodiola rosea L. extract on behavioural and physiological alterations induced by chronic mild stress in female rats. Journal of Psychopharmacology. 2008 May 30. doi:10.1177/0269881108089872 PMID 18515456