Stevioside

from Wikipedia, the free encyclopedia
Structural formula
Structure of stevioside
General
Surname Stevioside
other names
  • 1- O - [(5 β , 8 α , 9 β , 10 α , 13 α ) - 13 - {[2 - O - ( β - D -glucopyranosyl) - β - D -glucopyranosyl] oxy} -18-oxocaur -16-en-18-yl] - β - D -glucopyranose ( IUPAC )
  • 19- O - β - D -glucopyranosyl-13- O - [ β - D -glucopyranosyl (1 → 2) - β - D -glucopyranosyl] -steviol
  • E 960
Molecular formula C 38 H 60 O 18
Brief description

colorless prisms

External identifiers / databases
CAS number 57817-89-7
EC number 260-975-5
ECHA InfoCard 100.055.414
PubChem 442089
ChemSpider 390625
Wikidata Q415043
properties
Molar mass 804.90 g mol −1
Physical state

firmly

Melting point

238-239 ° C

solubility

poor in water (1.25 g · l −1 ), better in ethanol

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Stevioside is a glycoside of the diterpene steviol from the leaves of the stevia plant ( Stevia rebaudiana bertoni , one of around 200 types of stevia worldwide), a natural sweetener and one of the main components of stevia . The leaves contain ten previously discovered sweeteners, with stevioside almost always making up the largest proportion. In a broader sense, the mixture of these sweeteners obtained by extraction is also referred to as stevioside . Steviol glycosides were approved as a food additive in the EU on November 12, 2011 with effect from December 2, 2011 under the designation E 960 .

chemistry

Steviol , the aglycon (that means deglycosylated form ) of stevioside

Stevioside has a tetracyclic ent - Kauran -Diterpen-backbone, the carboxy group at C-18 with the 1 β - hydroxy group of a D -glucopyranose esterified , while the hydroxy group at C-13 glycosidically with the disaccharide sophorose (2- O - β -Glucopyranosyl- D -glucose) is linked. It can be enzymatically split into the aglycon steviol and three molecules of glucose.

properties

Stevioside is a - in the purified form - white to light yellowish fine powder, similar to powdered sugar. Because it is easier to dose, there are various liquid solutions from thin to slightly viscous consistencies . The color of the clear solutions is colorless to pale yellow.

Properties as a sweetener

The sweetening power has a very wide range and is between about 70 and 450 times that of cane sugar . The value depends on various factors:

  • Proportion of the individual sweeteners in the mixture;
  • Purity , d. H. Share of all sweeteners in the total mass;
  • pH of the preparation in which the stevioside is used;
  • maximum temperature to which the stevioside is exposed - the higher the temperature, the lower the sweetening power.

The taste profile of stevioside is ideally almost that of the reference substance sugar. In the correct dosage, it tastes neutral sweet and full-bodied. The taste lasts a little longer than sugar. If dosed too high, stevioside tastes unpleasantly bitter. A bitter aftertaste or aftertaste can occur with inferior quality even with the correct dosage.

Stevioside is almost calorie-free and does not ferment in preparations such as beverages. It inhibits caries and plaque , is heat-resistant up to approx. 200 ° C and is therefore also suitable for cooking and baking. Stevioside improves and enhances taste, which is why it is also used in products such as pickled preserves and mustard . It has no addiction potential .

The purity is between 85% and 99.99%, with the end consumer products mostly being between 90% and 95% pure. The rest consists of other plant components and residual moisture. The percentage of dry matter in the leaves varies between 4% and 20% (all sweeteners combined) depending on the growing conditions and breeding.

Components in the sweetener mix

Properties and sweetness of various steviol glycosides
Steviol glycoside Molecular formula L (H 2 O) at 25 ° C
in g / l		 Sweetness
sucrose = 1
Dulcoside C 38 H 60 O 17 5.8 030th
Rebaudioside A C 44 H 70 O 23 8.0 200-300
Rebaudioside B C 38 H 60 O 18 1.1 150
Rebaudioside C C 44 H 70 O 22 2.1 030th
Rebaudioside D C 50 H 80 O 28 1.0 221
Steviol bioside C 32 H 50 O 13 0.3 090
Stevioside C 38 H 60 O 18 1.25 150-250

The most important individual sweeteners in the leaves and thus in the stevioside mixture are, in addition to stevioside (5% to 10%), rebaudioside A (2% to 4%) and rebaudioside C (1% to 2%), dulcoside  A (0 , 2% to 0.7%), the rebaudiosides B + D – F and the steviol bioside.

The proportion of the individual sweeteners in the total stevioside mass can vary greatly, which in turn has a very large influence on the quality and taste. Rebaudiosid A has the best taste and the highest sweetness, up to 450 times that of sucrose .

toxicology

After reviewing numerous older and more recent studies, the ANS, a panel of experts from the European Food Safety Authority, came to the conclusion that steviol glycosides are neither genotoxic nor carcinogenic, nor do they have any negative effects on fertility and human reproductive organs. An assessment of the risk for previously exposed persons with inflammatory bowel diseases or allergies is not yet possible.

The steviol glycoside leads to acute kidney failure in hamsters at the mean lethal dose of 5.2 g / kg body weight, since they have a different metabolism than humans. From a two-year study to investigate the possible toxicity and carcinogenicity of stevioside in rats, an allowable daily dose (ADI) for humans of 7.9 mg per kg body weight is considered safe. In June 2008, the expert panel of the Food and Agriculture Organization (FAO) and the World Health Organization (WHO), the Joint FAO / WHO Expert Committee on Food Additives (JECFA), set a permitted daily dose of 4 mg per kg body weight for stevioside as safe.

A follow-up study by the same committee of experts in 2006 reported studies with stevia extracts in animals and humans and concluded that stevioside and rebaudioside A are not genotoxic, either in vitro or in vivo, and that the genotoxicity of steviol and some of its derivatives, the show up in vitro, do not occur in vivo. The study also found no evidence of a carcinogenic effect. The potential positive health benefits steviosides may have in patients with high blood pressure or type 2 diabetes have also been pointed out, but further studies would be needed to determine the exact dosage.

Study results in the rat showed inconsistent results.

Legal situation

Since December 2, 2011, steviol glycoside has been approved as a sweetener in several food categories in the EU . Previously it was not approved on the European market, but could still be used in individual countries such as France (after a limited approval) and Germany (after a court ruling obtained sales approval in foods such as yoghurts). After the European Food Safety Authority had established its safety in studies on April 14, 2010 , Europe-wide approval had already been expected.

Until the end of 2011, stevioside, the stevia plant itself, and its dried leaves were not allowed to be sold as a food additive in the EU, after the EU Commission refused approval in 2000 (under the Novel Food Regulation). This decision was based on an opinion of June 17, 1999 by the Scientific Committee on Food of the EU Commission (SCF) that the safety studies on stevioside are not sufficient to prove the safety.

The use of stevia extract and stevioside as a sweetener in food has been permitted in Switzerland and in some South American and Asian countries (including Brazil, South Korea and Japan) for longer than in the EU. In the United States, the use of stevioside as a sweetener in foods was completely banned by the Food and Drug Administration (FDA) in 1991 due to concerns about the possible carcinogenicity of the sweetener. This was initially followed in 1995 by a release for sale as a dietary supplement , until limited use as a food additive was released in 2008.

literature

Web links

Wiktionary: Stevioside  - explanations of meanings, word origins, synonyms, translations

Individual evidence

  1. ↑ a b c d e f g h Entry on stevioside. In: Römpp Online . Georg Thieme Verlag, accessed on November 16, 2011.
  2. ↑ Stevioside data sheet from Sigma-Aldrich , accessed on April 17, 2017 ( PDF ).Template: Sigma-Aldrich / name not given
  3. ↑ a b COMMISSION REGULATION (EU) No. 1131/2011 of November 11, 2011 amending Annex II of Regulation (EC) No. 1333/2008 of the European Parliament and of the Council with regard to steviol glycosides. (PDF) Official Journal of the European Union, L 295/205, November 12, 2011.
  4. ↑ GIT Labor-Fachzeitschrift 12/2012 p. 873, accessed October 30, 2012, Jana Boden: Stevia in sight
  5. ^ A b Science Online Lexica: Entry on "Stevia rebaudiana" in the Lexicon of Medicinal Plants and Drugs. Retrieved November 16, 2011.
  6. ↑ a b EFSA : EFSA assesses the safety of steviol glycosides. April 14, 2010.
  7. ↑ EFSA : Scientific Opinion on the safety of steviol glycosides for the proposed uses as a food additive. March 10, 2010.
  8. ↑ C. Toskulkao et al: Acute toxicity of stevioside, a natural sweetener, and its metabolite, steviol, in several animal species. In: Drug Chem Toxicol . Volume 20, 1997, pp. 31-44. PMID 9183561 .
  9. ↑ L. Xili et al .: Chronic oral toxicity and carcinogenicity study of stevioside in rats. In: Food Chem. Toxicol. Volume 30, 1992, pp. 957-965. PMID 1473789 .
  10. ↑ DJ Benford, M. DiNovi, J. Schlatter: Safety Evaluation of Certain Food Additives: Steviol Glycosides . In: World Health Organization Joint FAO / WHO Expert Committee on Food Additives [JECFA] (Ed.): WHO Food Additives Series . tape 54 , 2006, pp. 140 (English, whqlibdoc.who.int [PDF; 18.0 MB ; accessed on November 7, 2016]).
  11. ↑ MS Melis: Effects of chronic administration of Stevia rebaudiana on fertility in rats. In: J Ethnopharmacol . 67 (2), Nov 1, 1999, pp. 157-161. PMID 10619379 .
  12. ↑ RM Oliveira-Filho, OA Uehara, CA Minetti, LB Valle: Chronic administration of aqueous extract of Stevia rebaudiana (Bert.) Bertoni in rats: endocrine effects. In: General Pharmacology . Volume 20, 1989, pp. 187-191. PMID 2785472 .
  13. ↑ V. Yodyingyuad, S. Bunyawong: Effect of stevioside on growth and reproduction. In: Hum Reprod. 6 (1), Jan 1991, pp. 158-165. PMID 1874950 .
  14. ↑ GM Planas, J. Kucacute: Contraceptive Properties of Stevia rebaudiana. In: Science . 162 (3857), Nov 29, 1968, p. 1007. PMID 17744732 .
  15. ↑ More transparency in food additives. European Commission, accessed November 14, 2011 .
  16. ↑ Decision 2000/197 / EC of the Commission of February 22, 2000 on the refusal of approval of Stevia rebaudiana Bertoni: Plants and dried leaves as novel foods or novel food ingredients in accordance with Regulation (EC) No. 258/97 of the European Parliament and of the Council ( Official Journal of the EC No. L 61 of March 8, 2000). eur-lex.europa.eu (PDF) .
  17. ^ Opinion of the Scientific Committee on Food of the EU Commission on the use of steviosides as sweeteners. (PDF; 37 kB) Translation
  18. ^ Opinion of the Scientific Food Committee of the EU Commission on "Stevia Rebaudiana Bertoni" plants and leaves. (PDF; 22 kB)