Chemistry: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 | |
PubChem CID
|
|
| UNII | |
| |
| |
| 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). | |
| Infobox references | |
Rebaudioside A, also known as 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.
Besides being used directly as a natural sweetener, Rebaudioside A is also a major raw material for the increasingly popular enzymatic conversion of Rebaudioside M.[4][5] In this process, the hydroxy groups at positions 2 and 3 of the beta-D-glucosyl ester moiety are both converted to the corresponding beta-D-glucoside.[6][7] Reb M offers a clean, sugar-like sweetness without the bitter aftertaste associated with earlier stevia extracts.
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 English). Comprehensive Natural Products II. 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."".
- ↑ 3.0 3.1 "Stevia (Stevia rebaudiana) a bio-sweetener: a review". International Journal of Food Sciences and Nutrition 61 (1): 1–10. 2010. doi:10.3109/09637480903193049. PMID 19961353.
- ↑ "Buy Bulk - Rebaudioside M (Reb M) | Manufacturer-Supplier" (in en-GB). 2025-04-20. https://sinofoodsupply.com/rebaudioside-m/.
- ↑ Castle, Laurence; Andreassen, Monica; Aquilina, Gabriele; Bastos, Maria Lourdes; Boon, Polly; Fallico, Biagio; FitzGerald, Reginald; Fernandez, Maria Jose Frutos et al. (2025-05-01). "Safety of the proposed amendment of the specifications of the food additive E960c(i) or E960c(ii)" (in en). EFSA Journal (John Wiley & Sons, Ltd) 23 (5). doi:10.2903/j.efsa.2025.9396. ISSN 1831-4732. PMID 40371316.
- ↑ Okonkwo, Clinton E.; Adeyanju, Adeyemi A.; Onyeaka, Helen; Nwonuma, Charles Obiora; Olaniran, Abiola F.; Alejolowo, Omokolade Oluwaseyi; Inyinbor, Adejumoke A.; Oluyori, Abimbola Peter et al. (November 2024). "A review on rebaudioside M: The next generation steviol glycoside and noncaloric sweetener" (in en). Journal of Food Science 89 (11): 6946–6965. doi:10.1111/1750-3841.17401. ISSN 0022-1147. PMID 39323262. https://ift.onlinelibrary.wiley.com/doi/10.1111/1750-3841.17401.
- ↑ PubChem. "Rebaudioside M" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/92023628.
 |  |
