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
(22R,25S,26R)-26-(α-L-Rhamnopyranosyl)-3β-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyloxy]-22,26-epoxy-5α-cholestan-6-one
Systematic IUPAC name
(12S,13R,14R,15R,16S,32R,33R,34S,35S,36R,51R,53aS,53bS,55aS,57S,59aR,59bS,511aS,6S,72R,75S,76R,92S,93R,94R,95R,96S)-13,14,15,34,35,93,94,95-Octahydroxy-36-(hydroxymethyl)-16,59a,511a,6,75,96-hexamethylhexadecahydro-55H-2,4,8-trioxa-1,9(2),3(3,2),7(2,6)-tetrakis(oxana)-5(7,1)-cyclopenta[a]phenanthrenanonaphan-55-one
Other names
26-O-α-L-Rhamnopyranosyl-(22R,25S,26R)-22,26-epoxy-6-oxo-5α-cholestan-3β,26-diol-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C45H74O17/c1-18-7-10-29(59-40(18)62-42-38(55)35(52)32(49)21(4)57-42)19(2)24-8-9-25-23-16-28(47)27-15-22(11-13-45(27,6)26(23)12-14-44(24,25)5)58-43-39(36(53)33(50)30(17-46)60-43)61-41-37(54)34(51)31(48)20(3)56-41/h18-27,29-43,46,48-55H,7-17H2,1-6H3/t18-,19-,20-,21-,22-,23-,24+,25-,26-,27+,29+,30+,31-,32-,33+,34+,35+,36-,37+,38+,39+,40+,41-,42-,43+,44+,45+/m0/s1
    Key: QZOALWMSYRBZSA-QZLZDTQYSA-N
  • CC1CCC(OC1OC2C(C(C(C(O2)C)O)O)O)C(C)C3CCC4C3(CCC5C4CC(=O)C6C5(CCC(C6)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(C(O8)C)O)O)O)C)C
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
  • Media related to Osladin at Wikimedia Commons


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