Title: Gaultherin
CAS Registry Number: 490-67-5
CAS Name: 2-[(6-O-b-D-Xylopyranosyl-b-D-glucopyranosyl)oxy]benzoic acid methyl ester
Additional Names: methyl salicylate-2-glucoxyloside; methyl salicylate-2-primeveroside; monotropitin; monotropitoside
Molecular Formula: C19H26O12
Molecular Weight: 446.40
Percent Composition: C 51.12%, H 5.87%, O 43.01%
Literature References: In the wintergreen plant, Gaultheria procumbens L., in Monotropa hypopitys L., Ericaceae in Betula lenta L., Betulaceae, in Spiraea ulmaria L. and S. filipendula L., Rosaceae: Bridel, Compt. Rend. 177, 642 (1923); 179, 991 (1924); 180, 1421, 1864 (1925); Bridel, Grillon, ibid. 187, 609 (1928). Synthesis: Robertson, Waters, J. Chem. Soc. 1931, 1881. On hydrolysis with 3% H2SO4 gaultherin forms 1 mol methyl salicylate, 1 mol D-glucose and 1 mol D-xylose. Enzymatic hydrolysis gives methyl salicylate and primeverose (glucoxylose).
Properties: Needles in star formation from 99% acetone. mp 180°. [a]D20 -58° (c = 2). Sol in water and alcohol, slightly sol in ethyl acetate, acetone. Insol in ether.
Melting point: mp 180°
Optical Rotation: [a]D20 -58° (c = 2)
Derivative Type: Gaultherioside
Additional Names: Ethyl primeveroside
Molecular Formula: C13H24O10
Molecular Weight: 340.32
Percent Composition: C 45.88%, H 7.11%, O 47.01%
Properties: mp 185°. [a]D -58°. Gaultherioside forms glucose, xylose, and EtOH on hydrolysis with 3% H2SO4.
Melting point: mp 185°
Optical Rotation: [a]D -58°
NOTE: The older literature regards gaultherin as methylsalicylate-D-glucoside.
Status: This monograph has been retired and is no longer subject to revision or update.

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