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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...

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Related Experiment Video

Updated: Jun 21, 2026

Transient Expression in Nicotiana Benthamiana Leaves for Triterpene Production at a Preparative Scale
08:56

Transient Expression in Nicotiana Benthamiana Leaves for Triterpene Production at a Preparative Scale

Published on: August 16, 2018

A new friedelane type triterpene from Euonymus hederaceus.

Cui-Rong Sun1, He-Jiao Hu, Run-Sheng Xu

  • 1Department of Chemistry, Zhejiang University, Hangzhou 310027, China. suncuirong@zju.edu.cn

Molecules (Basel, Switzerland)
|July 28, 2009
PubMed
Summary

Researchers discovered a new friedelane triterpene, 28-hydroxyfriedelan-3-one-29-oic acid, from Euonymus hederaceus. This compound, isolated from the plant

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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

Published on: October 4, 2019

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Last Updated: Jun 21, 2026

Transient Expression in Nicotiana Benthamiana Leaves for Triterpene Production at a Preparative Scale
08:56

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Published on: August 16, 2018

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
07:59

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

Published on: October 4, 2019

Area of Science:

  • Natural Product Chemistry
  • Phytochemistry
  • Medicinal Plant Research

Background:

  • Euonymus hederaceus, widely found in southern China, has a history of traditional medicinal use.
  • Folk applications include treatments for renal deficiency, chronic diarrhea, traumatic injuries, and abnormal menstruation.

Purpose of the Study:

  • To conduct a chemical investigation of Euonymus hederaceus stems and leaves.
  • To isolate and characterize novel chemical compounds from the plant.

Main Methods:

  • High-resolution mass spectrometry (HRMS) for molecular mass and formula determination.
  • Nuclear Magnetic Resonance (NMR) spectroscopy, including 1D (1H, 13C, DEPT135) and 2D NMR, for structural elucidation.
  • Infrared (IR) spectroscopy to confirm functional groups.

Main Results:

  • Isolation and first-time characterization of a new friedelane-type triterpene.
  • The new compound has a molecular mass of 472 and molecular formula C30H48O4.
  • The structure was identified as 28-hydroxyfriedelan-3-one-29-oic acid based on comprehensive spectroscopic data.

Conclusions:

  • The study successfully identified a new triterpene, 28-hydroxyfriedelan-3-one-29-oic acid, from Euonymus hederaceus.
  • This finding contributes to the understanding of the chemical constituents of Euonymus hederaceus.
  • Further research may explore the pharmacological activities of this newly identified compound.