Stevioside

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
CAS Number	57817-89-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:9271
ChEMBL	ChEMBL444122
ChemSpider	390625
ECHA InfoCard	100.055.414
EC Number	260-975-5
KEGG	C09189
PubChem CID	442089
UNII	0YON5MXJ9P
CompTox Dashboard (EPA)	DTXSID7021281
InChI 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
SMILES 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
Chemical formula	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]

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). ^[2] Stevioside was discovered in 1931 by French chemists who gave it its name. ^[2] The sweetening power of stevioside was estimated to be about 300 times stronger than cane sugar. ^[2]

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 use as an ingredient in manufactured foods. ^[3]

See also

• Steviol glycoside

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. 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.
3. Perrier JD, Mihalov JJ, Carlson SJ (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. PMID   30268795.