Stevioside

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Stevioside
Stevioside.svg
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
Preferred 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 Edit this at Wikidata
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

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]

Origin[edit]

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]

See also[edit]

References[edit]

  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. ^ a b c Scientific Committee on Food (17 June 1999). "Opinion On Stevioside as a Sweetener" (PDF). The European Commission.