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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.[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]

Rebaudioside A
Names
IUPAC name
β-D-Glucopyranose 1-(13-{β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyloxy}-5β,8α,9β,10α,13α-kaur-16-en-18-oate)
Preferred 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
  • 58543-16-1
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:145012
ChEMBL
  • ChEMBLCHEMBL430341
ChemSpider
  • 5294031
ECHA InfoCard 100.121.892
  • 124378
UNII
  • B3FUD0528F Y
  • DTXSID8047898
  • [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 [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).

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.

References

  1. ^ Rebaudioside A MATERIAL SAFETY DATA SHEET November 6, 2006
  2. ^ 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.
  3. ^ 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.

rebaudioside, sometimes, shortened, steviol, glycoside, from, leaves, stevia, rebaudiana, that, times, sweeter, than, sugar, sweetest, most, stable, steviol, glycoside, less, bitter, than, stevioside, stevia, leaves, contain, stevioside, rebaudioside, namesiup. 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 Rebaudioside A NamesIUPAC name b D Glucopyranose 1 13 b D glucopyranosyl 1 2 b D glucopyranosyl 1 3 b D glucopyranosyloxy 5b 8a 9b 10a 13a kaur 16 en 18 oate Preferred 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 carboxylateIdentifiersCAS Number 58543 16 13D model JSmol Interactive imageChEBI CHEBI 145012ChEMBL ChEMBLCHEMBL430341ChemSpider 5294031ECHA InfoCard 100 121 892PubChem CID 124378UNII B3FUD0528F YCompTox Dashboard EPA DTXSID8047898SMILES 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 PropertiesChemical formula C44H70O23 1 Molar mass 967 01 g molAppearance white powderExcept 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 References Edit 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 This article about an organic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Rebaudioside A amp oldid 1107374469, wikipedia, wiki, book, books, library,

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