Received 11 December 2012
aDepartment of Medicinal Chemistry, University of Mississippi, 417 Faser Hall, University, MS 38677, USA,bIronstone Separations, Inc., 147 County Road 245, Etta, Mississippi 38627, USA, and cDepartment of Chemistry and Biochemistry, University of Mississippi, 417 Faser Hall, University, MS 38677, USA
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Stevioside is a naturally occurring diterpenoid glycoside in Stevia rebaudiana Bertoni. The title compound, C38H60O18·4CH3OH, crystallized as its methanol tetrasolvate. Stevioside consists of an aglycone steviol (a tetracyclic diterpene in which the four-fused-ring system consists of three six-membered rings and one five-membered ring) and a sugar part (three glucose units). A weak intramolecular O-HO hydrogen bond occurs. In the crystal, the methanol molecules participate in a two-dimensional hydrogen-bonded network parallel to b axis with the sugars and together they form a hydrophilic tunnel which encloses the lipophilic part of the molecule.
For low-calorie sweeteners, see: Bertoni (1905); Kinghorn (2002). For the Joint FAO/WHO Expert Committee on Food Additives, see: JECFA (2010). For the US Food and Drug Administration granted regulatory acceptance of Rebaudioside A, see: FDA (2008) and of mixtures of steviol glycosides, see: FDA (2010). For European Union approved steviol glycosides, see: OJ L (2011). For commercilization of glycoside sweeteners from S. rebaudiana, see: Prakash et al. (2008); Wölwer-Rieck (2012). For a related structure, see: Prakash & Upreti (2011). For puckering parameters, see: Cremer & Pople (1975).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2161 ).
This work was funded through Ironstone Separations, Inc., 147 County Road 245, Etta, Mississippi, USA, 38627.
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