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
CAS Number	58543-16-1
3D model (JSmol)	Interactive image
ChEBI	CHEBI:145012
ChEMBL	ChEMBLCHEMBL430341
ChemSpider	5294031
ECHA InfoCard	100.121.892
PubChem CID	124378
UNII	B3FUD0528F^Y
CompTox Dashboard (EPA)	DTXSID8047898
SMILES [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
Chemical formula	C₄₄H₇₀O₂₃ ^[1]
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

Rebaudioside A (sometimes shortened to "Reb A") is a steviol glycoside from the leaves of Stevia rebaudiana that is 240 times sweeter than sugar.^[2] Rebaudioside A is the sweetest and most stable steviol glycoside, and is less bitter than stevioside.^[3] Stevia leaves contain 9.1% stevioside and 3.8% rebaudioside A.^[3]

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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References

^ Rebaudioside A MATERIAL SAFETY DATA SHEET November 6, 2006
^ Izawa, Kunisuke; Amino, Yusuke; Kohmura, Masanori; Ueda, Yoichi; Kuroda, Motonaka (2010). "4.16 - Human–Environment Interactions – Taste". In Liu, Hung-Wen (Ben); Mander, Lew (eds.). Comprehensive Natural Products II. Vol. 4. Elsevier. pp. 631–671. doi:10.1016/B978-008045382-8.00108-8. ISBN 978-0-08-045382-8. Among the glycosides, stevioside is the most abundant followed by rebaudioside A. Stevioside is 140 times sweeter than sucrose, while rebaudioside is 240 times sweeter.
^ ^a ^b Goyal SK, Samsher, Goyal RK (2010). "Stevia (Stevia rebaudiana) a bio-sweetener: a review". International Journal of Food Sciences and Nutrition. 61 (1): 1–10. doi:10.3109/09637480903193049. PMID 19961353. S2CID 24564964.

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This page was last edited on 6 May 2023, at 22:53

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