Osladin

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 (1^2S,1^3R,1^4R,1^5R,1^6S,3^2R,3^3R,3^4S,3^5S,3^6R,5^1R,5^3aS,5^3bS,5^5aS,5^7S,5^9aR,5^9bS,5^11aS,6S,7^2R,7^5S,7^6R,9^2S,9^3R,9^4R,9^5R,9^6S)-1^3,1^4,1^5,3^4,3^5,9^3,9^4,9^5-Octahydroxy-3^6-(hydroxymethyl)-1^6,5^9a,5^11a,6,7^5,9^6-hexamethylhexadecahydro-5^5H-2,4,8-trioxa-1,9(2),3(3,2),7(2,6)-tetrakis(oxana)-5(7,1)-cyclopenta[a]phenanthrenanonaphan-5^5-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	33650-66-7^Y
3D model (JSmol)	Interactive image
ChemSpider	8616159
PubChem CID	441890
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/s1 Key: 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^−1
Appearance	White crystals[1]
Melting point	202 to 204 °C (396 to 399 °F; 475 to 477 K)[1]
Solubility in water	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). Y verify (what is ^YN ?) Infobox references

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]

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

• Sugar substitute
• Glycyrrhizin

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