Stevioside

Last updated
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
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 260-975-5
KEGG
PubChem CID
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
Appearancewhite powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

Contents

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

Related Research Articles

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<span class="mw-page-title-main">Stevia</span> Sweetener and sugar substitute

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In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.

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<i>Stevia rebaudiana</i> Species of flowering plant

Stevia rebaudiana is a plant species in the genus Stevia of the family Asteraceae. It is commonly known as candyleaf, sweetleaf or sugarleaf.

<span class="mw-page-title-main">Sweetness</span> Basic taste

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<i>Gymnema sylvestre</i> Species of flowering plant

Gymnema sylvestre is a perennial woody vine native to Asia, Africa and Australia. It has been used in Ayurvedic medicine. Common names include gymnema, Australian cowplant, and Periploca of the woods, and the Hindi term gurmar, which means "sugar destroyer".

<span class="mw-page-title-main">Steviol glycoside</span> Sweet chemicals derived from the Stevia plant

Steviol glycosides are the chemical compounds responsible for the sweet taste of the leaves of the South American plant Stevia rebaudiana (Asteraceae) and the main ingredients of many sweeteners marketed under the generic name stevia and several trade names. They also occur in the related species S. phlebophylla and in the plant Rubus chingii (Rosaceae).

<span class="mw-page-title-main">Steviol</span> Chemical compound

Steviol is a diterpene first isolated from the plant Stevia rebaudiana in 1931. Its chemical structure was not fully elucidated until 1960.

Rebiana is the trade name for high-purity rebaudioside A, a steviol glycoside that is 200 times as sweet as sugar. It is derived from stevia leaves by steeping them in water and purifying the resultant extract to obtain the rebaudioside A. The Coca-Cola Company filed patents on rebiana, and in 2007 it licensed the rights to the patents for food products to Cargill; Coca-Cola retained the exclusive rights to use the patents for beverage products. Truvia and PureVia are each made from rebiana and were each recognized as GRAS food ingredients by the US FDA in 2008.

The enzyme ent-kaurene synthase catalyzes the chemical reaction

PureVia is a stevia-based low calorie sugar substitute developed jointly by PepsiCo and Whole Earth Sweetener Company which is a wholly owned subsidiary of artificial sweetener manufacturing company Merisant.

<span class="mw-page-title-main">Rebaudioside A</span> Chemical compound

Rebaudioside A is a steviol glycoside from the leaves of Stevia rebaudiana that is 240 times sweeter than sugar. Rebaudioside A is the sweetest and most stable steviol glycoside, and is less bitter than stevioside. Stevia leaves contain 9.1% stevioside and 3.8% rebaudioside A.

<span class="mw-page-title-main">PureCircle</span>

PureCircle is a producer and innovator in the area of stevia sweeteners for the food and beverage industry. PureCircle has offices around the world, with the headquarters in Chicago, Illinois. It was listed on the London Stock Exchange until it was acquired by Ingredion in July 2020.

<i>Stevia</i> (genus) Family of shrubs

Stevia is a genus of about 240 species of herbs and shrubs in the family Asteraceae, native to subtropical and tropical regions from western North America to South America.

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. 1 2 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 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.