Rosavin

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Rosavin
Names
IUPAC name
(2E)-3-Phenylprop-2-en-1-yl α-L-arabinopyranosyl-(1→6)-α-D-glucopyranoside
Systematic IUPAC name
(2S,3R,4S,5S,6R)-2-{[(2E)-3-Phenylprop-2-en-1-yl]oxy}-6-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol
Identifiers
3D model (JSmol)
ChEBI
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
  • C1[C@@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC/C=C/C3=CC=CC=C3)O)O)O)O)O)O
Properties
C20H28O10
Molar mass 428.434 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Rosavin is a chemical compound with the molecular formula C20H28O10. It is a diglycoside of cinnamyl alcohol. Rosavin and related glycosides of cinnamyl alcohol, including rosin and rosarin, are key chemical constituents of Rhodiola rosea L., (R. rosea). R. rosea is an important medicinal plant commonly used throughout Europe, Asia, and North America, that has been recognized as a botanical adaptogen by the European Medicines Agency.[1] Rosavin production is specific to R. rosea and R. sachalinenis,[2] and the biosynthesis of these glycosides occurs spontaneously in Rhodiola roots and rhizomes.[3] The production of rosavins increases in plants as they get older, and the amount of the cinnamyl alcohol glycosides depends on the place of origin of the plant.[4]

Applications

References

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