Osladin

Last updated
Osladin
Osladin.svg
Names
IUPAC name
26-O-α-L-Rhamnopyranosyl-(22R,25S,26R)-22,26-epoxy-6-oxo-5α-cholestan-3β,26-diol-3-O-α-L-rhamnopyrano-syl-(1→2)-β-D-glucopyranoside
Preferred 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
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • 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
AppearanceWhite 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

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]

Contents

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

Related Research Articles

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Sugar substitute Food additive

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Acesulfame potassium chemical compound

Acesulfame potassium, also known as acesulfame K or Ace K, is a calorie-free sugar substitute often marketed under the trade names Sunett and Sweet One. In the European Union, it is known under the E number E950. It was discovered accidentally in 1967 by German chemist Karl Clauss at Hoechst AG. In chemical structure, acesulfame potassium is the potassium salt of 6-methyl-1,2,3-oxathiazine-4(3H)-one 2,2-dioxide. It is a white crystalline powder with molecular formula C
4
H
4
KNO
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S
and a molecular weight of 201.24 g/mol.

Glycoside Molecule in which a sugar is bound to another functional group

In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.

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<i>Stevia rebaudiana</i>

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Alitame Chemical compound

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Sweetness Basic taste

Sweetness is a basic taste most commonly perceived when eating foods rich in sugars. Sweet tastes are generally regarded as pleasurable, except when in excess. In addition to sugars like sucrose, many other chemical compounds are sweet, including aldehydes, ketones, and sugar alcohols. Some are sweet at very low concentrations, allowing their use as non-caloric sugar substitutes. Such non-sugar sweeteners include saccharin and aspartame. Other compounds, such as miraculin, may alter perception of sweetness itself.

<i>Gymnema sylvestre</i> Species of flowering plant

Gymnema sylvestre is a perennial woody vine native to tropical Asia, China, the Arabian Peninsula, Africa, and Australia. It has been used in Ayurvedic medicine. Common names include gymnema, Australian cowplant, and Periploca of the woods, and the Hindi term gurmar, which means "sugar destroyer".

Brazzein

Brazzein is a sweet-tasting protein extracted from the West African fruit of the climbing plant Oubli. It was first isolated by the University of Wisconsin–Madison in 1994.

Mogroside

A mogroside is a glycoside of cucurbitane derivatives found in certain plants, such as the fruit of the gourd vine, luo han guo. Mogrosides are extracted from S. grosvenorii and used in the manufacture of sugar substitutes.

Steviol glycoside

Steviol glycosides are the chemical compounds responsible for the sweet taste of the leaves of the South American plant Stevia rebaudiana (Asteraceae) and the main ingredients of many sweeteners marketed under the generic name stevia and several trade names. They also occur in the related species Stevia phlebophylla and in the plant Rubus chingii (Rosaceae).

<i>Polypodium vulgare</i> Species of ferns in the family Polypodiaceae

Polypodium vulgare, the common polypody, is a fern of the family Polypodiaceae. Polypodium vulgare is an allotetraploid species, believed to have arisen by chromosome doubling of a sterile diploid hybrid between two ferns which are not known in Europe. The fern's proposed parents are the northern Asian and northern North American Polypodium sibiricum and western North American Polypodium glycyrrhiza. Biochemical data point to a species from eastern Asia as the second possible parent. The name is derived from poly (many) and pous, podos . Polypody has traditional uses in cooking for its aroma and sweet taste, and in herbal medicine as a purgative and vermifuge.

<i>Thaumatococcus daniellii</i>

Thaumatococcus daniellii is a plant species from Africa, known for being the natural source of thaumatin, an intensely sweet protein which is of interest in the development of sweeteners. When the fleshy part of the fruit is eaten, this molecule binds to the tongue's taste buds, causing sour foods to taste sweet. It is a large, rhizomatous, flowering herb native to the rainforests of western Africa from Sierra Leone to Democratic Republic of the Congo. It is also an introduced species in Australia and Singapore.

<i>Polypodium glycyrrhiza</i> Species of ferns in the family Polypodiaceae

Polypodium glycyrrhiza, commonly known as licorice fern, many-footed fern, and sweet root, is a summer deciduous fern native to western North America, where it is found in shaded, damp locations.

Rebaudioside A Chemical compound

Rebaudioside A is a steviol glycoside from the leaves of Stevia rebaudiana that is 240 times sweeter than sugar. Rebaudioside A is the sweetest and most stable steviol glycoside, and is less bitter than stevioside. Stevia leaves contain 9.1% stevioside and 3.8% rebaudioside A.

Selligueain A Chemical compound

Selligueain A is an A type proanthocyanidin trimer of the propelargonidin type.

References

  1. 1 2 3 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. 1 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