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S3572

Sigma-Aldrich

Stevioside hydrate

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

Synonym(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

Empirical Formula (Hill Notation):
C38H60O18 · xH2O
CAS Number:
57817-89-7
Molecular Weight:
804.87 (anhydrous basis)
UNSPSC Code:
12352200
PubChem Substance ID:
329824534
NACRES:
NA.77

product name

Stevioside hydrate, ≥98% (HPLC)

biological source

Stevia sp.

assay

≥98% (HPLC)

form

powder

color

white

solubility

DMSO: 25 mg/mL, clear

storage temp.

2-8°C

SMILES string

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

InChI key

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.

Biochem/physiol Actions

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.

Preparation Note

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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)
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
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