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Stevioside

$85

  • Brand : BIOFRON

  • Catalogue Number : BF-S1019

  • Specification : 98%

  • CAS number : 57817-89-7

  • Formula : C20H30O3

  • Molecular Weight : 318.45

  • PUBCHEM ID : 442089

  • Volume : 20mg

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Catalogue Number

BF-S1019

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

318.45

Appearance

White crystalline powder

Botanical Source

Stevia rebaudiana

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC12CCCC(C1CCC34C2CCC(C3)(C(=C)C4)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)(C)C(=O)OC7C(C(C(C(O7)CO)O)O)O

Synonyms

Steviosides/(1R,4S,5R,9S,10R,13S)-13-{[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}tetrahydro-2H-pyran-2-yl]oxy}-5,9-dimethyl-14-methylenetetracyclo[11.2.1.0.0]hexadecane-5-carboxylate de (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yle/(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl-(1R,4S,5R,9S,10R,13S)-13-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}tetrahydro-2H-pyran-2-yl]oxy}-5,9-dimethyl-14-methylentetracyclo[11.2.1.0.0]hexadecan-5-carboxylat/1-O-[(5β,8α,9β,10α,13α)-13-{[2-O-(β-D-Glucopyranosyl)-β-D-glucopyranosyl]oxy}-18-oxokaur-16-en-18-yl]-β-D-glucopyranose/Steviosin/(4,α)-13-[(2-O-β-D-Glucopyranosylalpha-D-glucopyranosyl)oxy]kaur-16-en-18-oic acid β-D-glucopyranosyl ester/Rebaudin/Stevioside/(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl (1R,4S,5R,9S,10R,13S)-13-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}tetrahydro-2H-pyran-2-yl]oxy}-5,9-dimethyl-14-methylenetetracyclo[11.2.1.0.0]hexadecane-5-carboxylate/1-O-{(5β,8α,9β,10α,13α)-13-[(2-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-18-oxokaur-16-en-18-yl}-β-D-glucopyranose

IUPAC Name

[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,4S,5R,9S,10R,13S)-13-[(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]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate

Applications

Density

1.5±0.1 g/cm3

Solubility

Methanol; Water; DMSO

Flash Point

290.3±27.8 °C

Boiling Point

963.3±65.0 °C at 760 mmHg

Melting Point

198°C

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:57817-89-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

28363166

Abstract

Diabetes mellitus is a chronic disease characterized by abnormal carbohydrate, lipid and protein metabolism due to a lack of insulin or reduced target cell sensitivity to insulin. Stevia rebaudiana is an important source of biochemically active substances with proven anti-diabetic effect. The aim of this study was to determine anti-diabetic effects of the low dose of stevioside in NMRI Haan mice. Aqueous stevioside solution (20mg/kg body weight) was administered by oral route of administration. Anti-diabetic effect of stevioside was estimated by oral glucose tolerance test, adrenaline test after a 10day stevioside treatment, and alloxan induced hyperglycaemia in mice (two experimental groups, 10day stevioside treatment before and after alloxan administration). Aqueous stevioside solution prevented significant increase in glycaemia in oral glucose tolerance test (9.22±1.13 to 9.85±1.32mmol/l, P<0.05), and not in adrenaline test. Significant difference in glycaemia was detected in mice pre-treated with saline and stevioside in alloxan induced hyperglycaemia (saline 23.32±2.14, stevioside 14.70±4.95mmol/l, P<0.05). In mice pre-treated with stevioside, smallest β cells loss was found compared to other alloxan treated groups. Preserved normal cytoarchitectonic arrangement in islets was detected. Based on the given results we presume there exist a potential therapeutic use of low dose stevioside in diabetes.

Copyright © 2017 Elsevier Masson SAS. All rights reserved.

KEYWORDS

Diabetes mellitus; Stevia rebaudiana; Stevioside

Title

Insight into anti-diabetic effect of low dose of stevioside.

Author

Ilić V1, Vukmirović S2, Stilinović N2, capo I3, Arsenović M4, Milijašević B2.

Publish date

2017 Jun

PMID

29328659

Abstract

We report short syntheses of (-)-tripterifordin and (-)-neotripterifordin, potent inhibitors of HIV replication, from stevioside, a natural sweetener used worldwide. The key transformations are reduction at C13 through the formation of a tertiary chloride and subsequent three-step lactonization including a selective iodination at C20 by the photoreaction of the C19-alcohol. The title compounds were reliably obtained from stevioside in 9 and 11 steps (with 5-7 isolation steps), respectively. Additionally, the related lactone-containing ent-kaurenes, doianoterpenes A and B, and two more natural products were synthesized.

Title

Syntheses of (-)-Tripterifordin and (-)-Neotripterifordin from Stevioside.

Author

Kobayashi S1, Shibukawa K1, Hamada Y1, Kuruma T1, Kawabata A1, Masuyama A1.

Publish date

2018 Feb 2

PMID

30059803

Abstract

The diterpenoids present highly varied oxidation patterns subjected to fascinating skeletal rearrangements, and possess antitumor, antibacterial, antihyperglycemic, anti-inflammatory activities and so on. While total synthesis is a possible solution to obtain required diterpenoid derivatives, the need for multisteps to build complex “privileged structures” is always prohibitive by semi-synthesis from naturally abundant related molecules. From this perspective, stevioside and its hydrolysis products steviol and isosteviol are good leads in the field of medicinal chemistry for diterpenoid drug discovery. Stevioside has a complex diterpenoid glycoside molecule comprised of an aglycone, steviol with the ent-kaurane skeleton and three molecules of glucose. Hydrolyzed under alkaline or acidic condition, stevioside generates ent-kaurane diterpenoid steviol or ent-beyerane diterpenoid isosteviol, respectively. Except for direct applications, they are widely used to provide ent-kaurane or ent-beyerane core structures for further medicinal chemistry study. Besides, these molecules also serve as model molecules, starting materials or catalysts in the field of synthetic chemistry. In this review, their biological activities and medicinal chemistry work are comprehensively summarized which are very helpful for diterpenoid drug exploration.

Copyright © 2018 Elsevier Masson SAS. All rights reserved.

KEYWORDS

Isosteviol; Lead exploration; Medicinal chemistry; Steviol; Stevioside

Title

Diterpenoid lead stevioside and its hydrolysis products steviol and isosteviol: Biological activity and structural modification.

Author

Wang M1, Li H1, Xu F1, Gao X1, Li J1, Xu S2, Zhang D2, Wu X2, Xu J2, Hua H1, Li D3.

Publish date

2018 Aug 5