Chemistry: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 Y 69306-80-5 (non-specific) Y
3D model (JSmol)	Interactive image
ChemSpider	4444255
EC Number	232-475-7
KEGG	C04183
PubChem CID	5280656
UNII	SVS3GU8AY8 Y
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

Tracking categories (test):

• SizeSet

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.

Sources

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