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Volume 69 
Part 3 
Pages o410-o411  
March 2013  

Received 11 December 2012
Accepted 8 February 2013
Online 20 February 2013

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.030
wR = 0.076
Data-to-parameter ratio = 12.0
Details
Open access

Stevioside methanol tetrasolvate

Yunshan Wu,a Douglas L. Rodenburg,b Mohamed A. Ibrahim,b James D. McChesneyb* and Mitchell A. Averya,c

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
Correspondence e-mail: jdmcchesney@ironstoneseparations.com

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-H...O 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.

Related literature

For low-calorie sweeteners, see: Bertoni (1905[Bertoni, M. S. (1905). An. Cientificos Parag. Ser. I, 5, 1-14.]); Kinghorn (2002[Kinghorn, A. D. (2002). In Stevia: The Genus Stevia. New York: Taylor & Francis.]). For the Joint FAO/WHO Expert Committee on Food Additives, see: JECFA (2010[JECFA (2010). Steviol Glycosides In: Compendium of Food Additive Specification (online edition) Food and Agriculture Organization of the United Nations (FAO) Joint FAO/WHO Expert Committee on Food Additives.]). For the US Food and Drug Administration granted regulatory acceptance of Rebaudioside A, see: FDA (2008[FDA (2008). US Food and Drug Administration, Agency Response Letter GRAS Notice No. GRN 000252, December 17, 2008.]) and of mixtures of steviol glycosides, see: FDA (2010[FDA (2010). US Food and Drug Administration Agency Response Letter GRAS Notice No. GRN 000304, March 22, 2010.]). For European Union approved steviol glycosides, see: OJ L (2011[OJ L (2011). L 295/205, 12.11.2011, p. 1.]). For commercilization of glycoside sweeteners from S. rebaudiana, see: Prakash et al. (2008[Prakash, I., DuBois, G. E., Clos, J. F., Wilkens, K. L. & Fosdick, L. E. (2008). Food Chem. Toxicol. 46, 575-582.]); Wölwer-Rieck (2012[Wölwer-Rieck, U. (2012). J. Agric. Food Chem. 60, 886-895.]). For a related structure, see: Prakash & Upreti (2011[Prakash, I. & Upreti, M. (2011). US Patent 8030481 B2.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1357-1358.]).

[Scheme 1]

Experimental

Crystal data

  • C38H60O18·4CH4O

  • Mr = 933.03

  • Monoclinic, P 21

  • a = 15.0413 (2) Å

  • b = 7.7866 (1) Å

  • c = 19.6443 (3) Å

  • [beta] = 96.231 (1)°

  • V = 2287.16 (5) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.92 mm-1

  • T = 100 K

  • 0.42 × 0.14 × 0.11 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1999[Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.699, Tmax = 0.906

  • 29032 measured reflections

  • 7325 independent reflections

  • 7174 reflections with I > 2[sigma](I)

  • Rint = 0.031
Refinement

  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.076

  • S = 1.05

  • 7325 reflections

  • 612 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2830 Friedel pairs

  • Flack parameter: 0.11 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4S-H4OS...O13i 0.84 1.90 2.7330 (17) 169
O3S-H3OS...O11i 0.84 1.88 2.7115 (19) 170
O2S-H2OS...O8ii 0.84 1.90 2.7381 (19) 177
O18-H18O...O2Siii 0.84 1.86 2.6857 (19) 167
O15-H15O...O10iv 0.84 2.22 3.0000 (19) 154
O14-H14O...O18v 0.84 1.91 2.6983 (19) 157
O13-H13O...O7iii 0.84 1.91 2.7080 (19) 158
O11-H11O...O3Svi 0.84 1.89 2.7248 (17) 169
O10-H10O...O16iv 0.84 1.88 2.7217 (18) 177
O7-H7O...O1Sv 0.84 1.96 2.777 (2) 166
O1S-H1OS...O1 0.84 2.08 2.860 (2) 154
O16-H16O...O4S 0.84 1.83 2.6558 (17) 168
O5-H5O...O3S 0.84 1.99 2.8081 (17) 166
O4-H4O...O15 0.86 2.38 3.2012 (17) 160
O3-H3O...O15 0.84 1.94 2.7569 (17) 165
Symmetry codes: (i) x-1, y, z; (ii) x-1, y+1, z; (iii) x+1, y-1, z; (iv) [-x+2, y+{\script{1\over 2}}, -z+1]; (v) x, y+1, z; (vi) [-x+2, y-{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2161 ).

Acknowledgements

This work was funded through Ironstone Separations, Inc., 147 County Road 245, Etta, Mississippi, USA, 38627.

References

Bertoni, M. S. (1905). An. Cientificos Parag. Ser. I, 5, 1-14.
Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2009). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1357-1358.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
FDA (2008). US Food and Drug Administration, Agency Response Letter GRAS Notice No. GRN 000252, December 17, 2008.
FDA (2010). US Food and Drug Administration Agency Response Letter GRAS Notice No. GRN 000304, March 22, 2010.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
JECFA (2010). Steviol Glycosides In: Compendium of Food Additive Specification (online edition) Food and Agriculture Organization of the United Nations (FAO) Joint FAO/WHO Expert Committee on Food Additives.
Kinghorn, A. D. (2002). In Stevia: The Genus Stevia. New York: Taylor & Francis.
OJ L (2011). L 295/205, 12.11.2011, p. 1.
Prakash, I., DuBois, G. E., Clos, J. F., Wilkens, K. L. & Fosdick, L. E. (2008). Food Chem. Toxicol. 46, 575-582.  [ISI] [PubMed]
Prakash, I. & Upreti, M. (2011). US Patent 8030481 B2.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wölwer-Rieck, U. (2012). J. Agric. Food Chem. 60, 886-895.  [ISI] [PubMed]

Acta Cryst (2013). E69, o410-o411   [ doi:10.1107/S1600536813003954 ]

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