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S3572

Sigma-Aldrich

Stevioside

from Stevia sp., ≥98% (HPLC), powder, p-aminohippurate transepithelial transport inhibitor

Synonyme(s) :

(4α-13-[(2-O-β-D-Glucopyranosyl-β-D-glucopyranosyl)oxy]kaur-16-en-18-oic acid β-D-glucopyranosyl ester

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About This Item

Formule empirique (notation de Hill):
C38H60O18 · xH2O
Numéro CAS:
57817-89-7
Poids moléculaire :
804.87 (anhydrous basis)
Code UNSPSC :
12352200
ID de substance PubChem :
329824534
Nomenclature NACRES :
NA.77

product name

Stevioside, ≥98% (HPLC)

Source biologique

Stevia sp.

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white

Solubilité

DMSO: 25 mg/mL, clear

Température de stockage

2-8°C

Chaîne SMILES 

O.C[C@@]12CCC[C@](C)(C1CC[C@]34CC(=C)[C@](CCC23)(C4)O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C(=O)O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O

InChI

1S/C38H60O18.H2O/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;1H2/t17-,18-,19-,20+,21+,22-,23-,24-,25+,26+,27+,28-,29-,30-,31+,32+,33+,35-,36-,37-,38+;/m1./s1

Clé InChI

FVECWZKNZGXJJO-QMYNVHDOSA-N

Application

Stevioside hydrate has been used as a standard in high performance liquid chromatography (HPLC) for quantification of steviol glycosides.
Stevioside-induced ROS-mediated apoptosis was studied in human breast cancer cells.

Actions biochimiques/physiologiques

Stevioside hydrate is a diterpene glycoside present in Stevia sp.
Stevioside is a noncaloric natural sweetener, 300 times more potent than sucrose. It inhibits transepithelial transport of p-aminohippurate (PAH) by interfering with the organic anion transport system. At 0.5-1 mM, it showed no interaction with any organic anion transporters (OAT).
Stevioside reportedly has genotoxic effects in cultured mammalian cells.

Notes préparatoires

Stevioside solutions should be prepared in DMSO. Highly pure stevioside has very poor water solubility.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves

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Consulter la Bibliothèque de documents

M Matsui et al.
Mutagenesis, 11(6), 573-579 (1996-11-01)
Stevioside, a constituent of Stevia rebaudiana, is commonly used as a non-caloric sugar substitute in Japan. The genetic toxicities of stevioside and its aglycone, steviol, were examined with seven mutagenicity tests using bacteria (reverse mutation assay, forward mutation assay, umu
Tadamasa Terai et al.
Chemical & pharmaceutical bulletin, 50(7), 1007-1010 (2002-07-20)
Stevioside is natural non-caloric sweetner isolated from Stevia rebaudiana BERTONI, which has been used as a non-caloric sugar substitute in Japan. Pezzuto et al. demonstrated that steviol shows a dose-dependent positive response in forward mutation assay using Salmonella typhimurium TM677
J M Pezzuto et al.
Proceedings of the National Academy of Sciences of the United States of America, 82(8), 2478-2482 (1985-04-01)
Stevioside, a constituent of Stevia rebaudiana, is commonly used as a noncaloric sugar substitute in Japan. Consistent with reports in the literature, we have found that stevioside is not mutagenic as judged by utilization of Salmonella typhimurium strain TM677, either
Evaluation of the euglycemic effect of oral administration of S. rebaudiana B. cultivated in Mexico in normoglycemic and induced-diabetic rats
Irma AG, et al.
International journal of environment, agriculture and biotechnology, 2(1) null
Determination of rebaudioside A and Stevioside in leaves of S. rebaudiana Bertoni grown in Mexico by a validated HPLC method
Aranda-Gonzalez I, et al.
American Journal of Analytical Chemistry, 6(11), 878-878 (2015)
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