Rebaudioside A

Rebaudioside A (sometimes shortened to "Reb 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.

Rebaudioside A
Names
IUPAC name
β-D-Glucopyranosyl 13-{β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyloxy}-5β,8α,9β,10α,13α-kaur-16-en-18-oate
Systematic IUPAC name
(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl (4R,4aS,6aR,9S,11aR,11bS)-9-{[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,11b-dimethyl-8-methylidenetetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.121.892
UNII
  • [C@]123[C@]([C@]4([C@@]([C@](CCC4)(C)C(O[C@@H]5O[C@@H]([C@@H](O)[C@@H]([C@H]5O)O)CO)=O)(CC1)[H])C)(CC[C@@](C2)(O[C@H]6[C@H](O[C@@H]7O[C@@H]([C@@H](O)[C@@H]([C@H]7O)O)CO)[C@H]([C@H](O)[C@H](O6)CO)O[C@@H]8O[C@@H]([C@@H](O)[C@@H]([C@H]8O)O)CO)C(C3)=C)[H]
Properties
C44H70O23
Molar mass 967.01 g/mol
Appearance white powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

The glycoside contains only glucose (to the exclusion of other commonly found monosaccharides) as its monosaccharide moieties. It contains four glucose molecules in total with the central glucose of the triplet connected to the main steviol structure at its hydroxyl group, and the remaining glucose at its carboxyl group forming an ester bond.

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