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Osladin

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Osladin
Names
IUPAC name (22R,25S,26R)-26-(α-L-Rhamnopyranosyl)-3β--22,26-epoxy-5α-cholestan-6-one
Systematic IUPAC name (1S,1R,1R,1R,1S,3R,3R,3S,3S,3R,5R,5S,5S,5S,5S,5R,5S,5S,6S,7R,7S,7R,9S,9R,9R,9R,9S)-1,1,1,3,3,9,9,9-Octahydroxy-3-(hydroxymethyl)-1,5,5,6,7,9-hexamethylhexadecahydro-5H-2,4,8-trioxa-1,9(2),3(3,2),7(2,6)-tetrakis(oxana)-5(7,1)-cyclopentaphenanthrenanonaphan-5-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
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
InChI
  • 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/s1Key: QZOALWMSYRBZSA-QZLZDTQYSA-N
SMILES
  • 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
Chemical formula C45H74O17
Molar mass 887.070 g·mol
Appearance White crystals
Melting point 202 to 204 °C (396 to 399 °F; 475 to 477 K)
Solubility in water Low in water. Soluble in ethanol.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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

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

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

External links

  • Media related to Osladin at Wikimedia Commons


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