rosavin

Rosavin is a chemical compound with the molecular formula . 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. Rosavin production is specific to R. rosea and R. sachalinenis, and the biosynthesis of these glycosides occurs spontaneously in Rhodiola roots and rhizomes. The productio

Chemical data

Formula: C20H28O10
Molecular weight: 428.4 g/mol
IUPAC name: (2R,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
SMILES: 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
InChIKey: RINHYCZCUGCZAJ-IPXOVKFZSA-N
XLogP: -2
Polar surface area: 158 Å²
H-bond donors: 6
H-bond acceptors: 10
Formal charge: 0

via PubChem

Wikidata facts

Mass: 428.168247096

Show 5 more facts

canonical SMILES: OC1COC(OCC2OC(OCC=CC=3C=CC=CC3)C(O)C(O)C2O)C(O)C1O
isomeric SMILES: O[C@H]1CO[C@@H](OC[C@H]2O[C@@H](OC/C=C/c3ccccc3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H]1O
chemical formula: C₂₀H₂₈O₁₀
found in taxon: Cinnamomum burmanni
Commons category: Rosavin

Sources (1)

wikidata.org

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Encyclopedic overview

3 sections

Contents

Biosynthesis
Applications
References

{{Chembox

| Name = | IUPACName = (2E)-3-Phenylprop-2-en-1-yl α-L-arabinopyranosyl-(1→6)-α-D-glucopyranoside | SystematicName = (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 | OtherNames = | data page pagename =

Excerpted from Wikipedia’s “rosavin” article, available under the CC BY-SA 4.0 licence.