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Related Concept Videos

Benzene to Phenol via Cumene: Hock Process01:27

Benzene to Phenol via Cumene: Hock Process

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The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene...
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Aromatic Compounds: Overview01:25

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In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday...
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Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration02:35

Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration

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Overview
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more...
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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Related Experiment Video

Updated: Aug 13, 2025

Transcript and Metabolite Profiling for the Evaluation of Tobacco Tree and Poplar as Feedstock for the Bio-based Industry
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Commiphora wildii Merxm. Essential Oil: Natural Heptane Source and Co-Product Valorization.

Djallel Mansouri1, Anne Landreau2, Thomas Michel1

  • 1Institut de Chimie de Nice, Université Côte d'Azur, CNRS UMR 7272, F-06108 Nice, France.

Molecules (Basel, Switzerland)
|January 21, 2023
PubMed
Summary

Commiphora wildii essential oil provides a sustainable source of heptane for perfumery extraction. The resulting heptane-depleted oil shows promising biological activities for cosmetic applications.

Keywords:
C. albicansC. glabrataCommiphora wildiico-product valorizationessential oilheptane

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Area of Science:

  • Natural Products Chemistry
  • Cosmetic Science
  • Green Chemistry

Background:

  • Traditional perfumery relies on fossil-derived hydrocarbon solvents.
  • Essential oils offer potential as sustainable alternatives.
  • Commiphora wildii oleo gum resin is explored as a novel source.

Purpose of the Study:

  • To isolate heptane from Commiphora wildii essential oil as a green solvent.
  • To evaluate the efficacy of isolated heptane in perfumery extractions.
  • To investigate the potential cosmetic applications of the heptane-depleted essential oil.

Main Methods:

  • Isolation of heptane via an innovative double distillation process.
  • Extraction of perfumery materials using isolated and fossil-based heptane.
  • Gas Chromatography-Mass Spectrometry (GC-MS) for chemical analysis.
  • In vitro bioassays for hyaluronidase, tyrosinase, antioxidant, elastase, and lipoxygenase inhibition.
  • Antimicrobial testing against skin-associated yeasts and bacteria.

Main Results:

  • Heptane was successfully isolated, comprising up to 30% of the oleo gum resin.
  • Extracts from Commiphora wildii-derived heptane showed superior sensory profiles.
  • 172 compounds were identified in the heptane-depleted essential oil.
  • The depleted oil demonstrated significant inhibitory effects in various bioassays.

Conclusions:

  • Commiphora wildii essential oil is a viable source for sustainable heptane production.
  • Heptane isolated from this source is an effective and potentially superior solvent for perfumery.
  • The heptane-depleted oil exhibits promising biological activities, making it a valuable ingredient for cosmetic applications.