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Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids01:02

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Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation easily. However, a silver salt of carboxylic acid reacts with bromine or iodine under high temperature to release carbon dioxide gas and forms halide with one less carbon. This reaction is called the Hunsdiecker reaction.
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Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.
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Tetrahydrocannabinol (THC) is a phytocannabinoid that primarily interacts with the CB1 receptor, a type of G protein-coupled receptor (GPCR) predominantly in and around the chemoreceptor trigger zone (CTZ) and emetic center. THC also blocks the serotonin receptor activity in the dorsal vagal complex (DVC) by inhibiting serotonin release. THC exerts its anti-emetic effects through these interactions, which are beneficial for patients undergoing chemotherapy.
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Nonenolizable Aldehydes to Acids and Alcohols: The Cannizzaro Reaction01:25

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The Cannizzaro reaction is a base-promoted redox reaction producing a primary alcohol and a carboxylic acid from two molecules of a nonenolizable aldehyde. The reaction commences when the anionic counterpart of the base attacks the carbonyl carbon, resulting in a tetrahedral alkoxide intermediate. The base then abstracts a proton from the intermediate to generate an unstable dianionic species. This intermediate enables the release of the aldehydic hydrogen as a hydride ion. An intermolecular...
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Carboxylic acids possess an acidic –COOH functional group. The acidity can be attributed to the resonance stabilization of their conjugate base, wherein the negative charge is delocalized over both oxygen atoms.
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There are various methods for the preparation of carboxylic acids. For example, oxidation of primary alcohols or aldehydes using strong oxidizing agents results in a carboxylic acid.  Aldehydes can also be oxidized in the presence of mild oxidizing agents.
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Ultrasonic-Assisted Extraction of Cannabidiolic Acid from Cannabis Biomass
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Acidic Cannabinoid Decarboxylation.

Crist N Filer1

  • 1PerkinElmer Health Sciences Inc., Waltham, Massachusetts, USA.

Cannabis and Cannabinoid Research
|September 22, 2021
PubMed
Summary

Cannabis acidic cannabinoids transform into neutral forms through decarboxylation. Understanding this process is key for cannabis cultivation and product development.

Area of Science:

  • Biochemistry
  • Plant Science
  • Organic Chemistry

Background:

  • Cannabis has been cultivated for millennia, with recent focus on its biosynthesis.
  • Acidic cannabinoids are key natural products of cannabis, with unique properties.
  • Understanding cannabinoid transformation is crucial for the cannabis industry.

Purpose of the Study:

  • To review the decarboxylation of acidic cannabinoids into neutral cannabinoids.
  • To explore the kinetics, mechanism, and occurrence of this reaction.
  • To discuss implications for cannabis cultivation and product development.

Main Methods:

  • Literature review of existing research on cannabinoid decarboxylation.
  • Analysis of chemical reactions and transformations of cannabinoids.
Keywords:
Cannabisacidic cannabinoiddecarboxylationneutral cannabinoid

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  • Synthesis of information regarding the timing and location of decarboxylation.
  • Main Results:

    • Acidic cannabinoids convert to neutral cannabinoids via decarboxylation, altering pharmacology.
    • Decarboxylation occurs under specific conditions, influenced by factors like heat.
    • Kinetics and mechanisms of this transformation are increasingly understood.

    Conclusions:

    • Cannabinoid decarboxylation is a significant biochemical process.
    • Controlling decarboxylation during harvest and storage is vital for stakeholders.
    • Further research can optimize cannabis cultivation and product quality.