Stevioside

Stevioside is a glycoside derived from the stevia plant, which can be used as a sweetener.[1] Evidence of benefit is lacking for long-term effects on weight loss and heart disease risks.[2]

Stevioside
Names
IUPAC name
β-D-Glucopyranosyl 13-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyloxy]-5β,8α,9β,10α,13α-kaur-16-en-18-oate
Systematic IUPAC name
(4R,4aS,6aR,9S,11aR,11bS)-9-{[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-{[(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 100.055.414
EC Number
  • 260-975-5
KEGG
UNII
  • InChI=1S/C38H60O18/c1-16-11-37-9-5-20-35(2,7-4-8-36(20,3)34(50)55-32-29(49)26(46)23(43)18(13-40)52-32)21(37)6-10-38(16,15-37)56-33-30(27(47)24(44)19(14-41)53-33)54-31-28(48)25(45)22(42)17(12-39)51-31/h17-33,39-49H,1,4-15H2,2-3H3/t17-,18-,19-,20+,21+,22-,23-,24-,25+,26+,27+,28-,29-,30-,31+,32+,33+,35-,36-,37-,38+/m1/s1
  • C[C@@]12CCC[C@@]([C@H]1CC[C@]34[C@H]2CC[C@](C3)(C(=C)C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)(C)C(=O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
Properties
C38H60O18
Molar mass 804.8722
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

Origin

Stevioside is the main sweetener (along with rebaudioside A) found in the leaves of Stevia rebaudiana, a plant originating in South America. Dried leaves, as well as aqueous extracts, have been used for decades as a sweetener in many countries, notably in Latin America and Asia (Japan, China).[3] Stevioside was discovered in 1931 by French chemists who gave it its name.[3] The sweetening power of stevioside was estimated to be about 300 times stronger than cane sugar.[3]

Safety

Since 2008, the U.S. Food and Drug Administration has not objected to the use of stevia extracts and some purified steviosides, mainly stevioside and rebaudioside, as GRAS for safe use as an ingredient in manufactured foods.[4]

See also

References
  1. Ceunen S, Geuns JM (June 2013). "Steviol glycosides: chemical diversity, metabolism, and function". Journal of Natural Products. 76 (6): 1201–28. doi:10.1021/np400203b. PMID 23713723.
  2. Azad MB, Abou-Setta AM, Chauhan BF, Rabbani R, Lys J, Copstein L, et al. (July 2017). "Nonnutritive sweeteners and cardiometabolic health: a systematic review and meta-analysis of randomized controlled trials and prospective cohort studies". CMAJ. 189 (28): E929–E939. doi:10.1503/cmaj.161390. PMC 5515645. PMID 28716847.
  3. Scientific Committee on Food (17 June 1999). "Opinion On Stevioside as a Sweetener" (PDF). The European Commission. Archived from the original (PDF) on 9 July 2006.
  4. Perrier, Judith D.; Mihalov, Jeremy J.; Carlson, Susan J. (2018). "FDA regulatory approach to steviol glycosides". Food and Chemical Toxicology. 122: 132–142. doi:10.1016/j.fct.2018.09.062. ISSN 0278-6915.
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