Rosin (chemical)

Rosin
Names
	IUPAC name (2E)-3-Phenylprop-2-en-1-yl β-D-glucopyranoside
	Systematic IUPAC name (2R,3S,4S,5R,6R)-2-(Hydroxymethyl)-6-{[(2E)-3-phenylprop-2-en-1-yl]oxy}oxane-3,4,5-triol
Identifiers
CAS Number	85026-55-7 ; 69306-80-5 (non-specific) ;
3D model (JSmol)	Interactive image;
ChemSpider	4444255;
EC Number	232-475-7;
KEGG	C04183;
PubChem CID	5280656;
UNII	SVS3GU8AY8 ;
CompTox Dashboard (EPA)	DTXSID60904535 ;
	InChI InChI=1S/C15H20O6/c16-9-11-12(17)13(18)14(19)15(21-11)20-8-4-7-10-5-2-1-3-6-10/h1-7,11-19H,8-9H2/b7-4+/t11-,12-,13+,14-,15-/m1/s1 Key: KHPCPRHQVVSZAH-GUNCLKARSA-N; InChI=1/C15H20O6/c16-9-11-12(17)13(18)14(19)15(21-11)20-8-4-7-10-5-2-1-3-6-10/h1-7,11-19H,8-9H2/b7-4+/t11-,12-,13+,14-,15-/m1/s1 Key: KHPCPRHQVVSZAH-GUNCLKARBM;
	SMILES C1=CC=C(C=C1)/C=C/CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O;
Properties
Chemical formula	C15H20O6
Molar mass	296.32 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Rosin is a glycoside ester of cinnamyl alcohol and a constituent of Rhodiola rosea.

Related compounds

The three cinnamyl alcohol-vicianosides of Rhodiola rosea, commonly referred to as "rosavins," are rosin, and the structurally related disaccharide rosavin, which is the arabinose ester of rosin, and rosarin, the arabinofuranose ester of rosin. Salidroside, common in Rhodiola spp. and occurring in Rhodiola rosea is not a cinnamyl alcohol glycoside, but a glycoside of tyrosol.^[1]

Sources

The cinnamyl alcohol glycosides rosin, rosavin and rosarin occur in the context of rhodiola species, only in Rhodiola rosea.^[1]

References

^ ^a ^b György, Zsuzsanna (2006-05-22). "Glycoside production by in vitro Rhodiola rosea cultures" (PDF). Acta Universitatis Ouluensis C Technica. 244. University of Oulu. ISBN 951-42-8080-6. ISSN 1796-2226.

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[auto-1] György, Zsuzsanna (2006-05-22). "Glycoside production by in vitro Rhodiola rosea cultures" (PDF). Acta Universitatis Ouluensis C Technica. 244. University of Oulu. ISBN 951-42-8080-6. ISSN 1796-2226.

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