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Related Concept Videos

Solvating Effects02:12

Solvating Effects

An understanding of the solvating effect helps rationalize the relation between solvation and acidity of the compound. In addition, this also explains the relative stability of conjugate bases for compounds with different pKa values. This lesson details, in-depth, the principle of solvating effects. The strength of an acid and the stability of its corresponding conjugate base are determined using pKa values. This observed relationship is a consequence of solvation, which is the interaction...
Stereoisomers02:32

Stereoisomers

On the basis of mirror symmetry, stereoisomers of an organic molecule can be further classified into diastereomers and enantiomers. Diastereomers are stereoisomers that are not mirror images of each other. Substituted alkenes, such as the cis and trans isomers of 2-butene, are diastereomers, as these molecules exhibit different spatial orientations of their constituent atoms, are not mirror images of each other, and do not interconvert. Here, the interconversion is suppressed due to restricted...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...

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Related Experiment Video

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Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
09:56

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Published on: September 6, 2019

Stevioside methanol tetra-solvate.

Yunshan Wu1, Douglas L Rodenburg, Mohamed A Ibrahim

  • 1Department of Medicinal Chemistry, University of Mississippi, 417 Faser Hall, University, MS 38677, USA.

Acta Crystallographica. Section E, Structure Reports Online
|March 12, 2013
PubMed
Summary

Stevioside, a natural sweetener from Stevia rebaudiana, was crystallized with methanol. Its structure reveals a steviol core linked to three glucose units, forming a unique hydrogen-bonded network with methanol molecules.

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Area of Science:

  • Natural Products Chemistry
  • Crystallography
  • Glycoscience

Background:

  • Stevioside is a key sweetening compound derived from the Stevia rebaudiana plant.
  • It is a diterpenoid glycoside with a complex molecular structure.

Purpose of the Study:

  • To elucidate the crystal structure of stevioside in its methanol tetrasolvate form.
  • To understand the intermolecular interactions and packing in the crystalline state.

Main Methods:

  • Single-crystal X-ray diffraction analysis.
  • Chemical characterization of the crystallized compound.

Main Results:

  • Stevioside crystallized as a methanol tetrasolvate (C38H60O18·4CH3OH).
  • The structure comprises a steviol aglycone linked to three glucose units.
  • A two-dimensional hydrogen-bonded network involving methanol and sugar moieties was observed, creating hydrophilic tunnels around the lipophilic steviol core.

Conclusions:

  • The crystal structure provides detailed insights into the molecular arrangement of stevioside.
  • The observed hydrogen-bonding network influences the compound's solid-state properties and interactions.