Osladin

Osladine is a high-intensity sweetener isolated from the rhizome of Polypodium vulgare.[3] It is a saponin, sapogenin steroid glycoside, 500 times sweeter than sucrose.[4]

Osladin
Names
IUPAC name
26-O-α-L-rhamnopyranosyl-(22R,25S,26R)-22,26-expoxy-6-oxo-5α-cholestan-3β,26-diol-3-o-α-L-rhamnopyrano-syl-(1→2)-β- D-glucopyranoside
Identifiers
3D model (JSmol)
ChemSpider
Properties
C45H74O17
Molar mass 887.070 g·mol−1
Appearance White crystals[1]
Melting point 202 to 204 °C (396 to 399 °F; 475 to 477 K)[1]
Low in water.[2] Soluble in ethanol.[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

A related compound, polypodoside A, has been identified from Polypodium glycyrrhiza and is 600 times sweeter than a sucrose solution at 6%.[2]

See also

References
  1. C.-R. Yang & O. Tanaka: Advances in Plant Glycosides, Chemistry and Biology. in Proceedings of the International Symposium on Plant Glycosides, August 12-15, 1997, Kunming, China; Elsevier, 1999. ISBN 978-0-444-50180-6
  2. AD Kinghorn & CM Compadre, Alternative Sweeteners: Third Edition, Revised and Expanded, Marcel Dekker, New York, 2001. ISBN 0-8247-0437-1
  3. J Jizba, L Dolejs, V Herout & F Sorm, « The structure of osladin — The sweet principle of the rhizomes of Polypodium vulgare L. », dans Tetrahedron Lett., vol. 18, 1971, p. 1329-1332 doi:10.1016/S0040-4039(01)96701-2
  4. Yamada, H. und Nishizawa, M. (1995): Synthesis and Structure Revision of Intensely Sweet Saponin Osladin. In: J Org Chem. 60(2); 386–397; doi:10.1021/jo00107a018
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