Stevioside

Stevioside
Names
	IUPAC name 13-[(2-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-ent-kaur-16-en-19-oic acid β-D-glucopyranosyl ester
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] Evidence of benefit is lacking for long term effects on weight loss and heart disease risks.^[2]

Origin

Stevioside is the main sweetener 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]

References

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

[pmid23713723-1] 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.

[EC-3] Scientific Committee on Food (17 June 1999). "Opinion On Stevioside as a Sweetener" (PDF). The European Commission.

[1]

[2]

[3]

Origin

See also

References