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Related Concept Videos

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

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Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

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Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
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Drug Toxicity: Allergic Reactions01:30

Drug Toxicity: Allergic Reactions

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Drug-related allergies are immune-mediated responses triggered by the administration of pharmacological agents. These hypersensitivity reactions are classified based on the immune mechanisms involved. The four primary types—Type I, II, III, and IV—are mediated by different immunological pathways and exhibit distinct clinical manifestations.Type I Hypersensitivity/ IgE-Mediated Reactions: Immunoglobulin E (IgE) immediately mediates Type I hypersensitivity reactions. Upon initial...
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Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

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Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
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Autoxidation of Ethers to Peroxides and Hydroperoxides02:23

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Ethers represent a class of chemical compounds that become more dangerous with prolonged storage because they tend to form explosive peroxides when standing in the air. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly oxidize to form hydroperoxides and dialkyl peroxides.
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Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

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Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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Formaldehyde Emissions From 2-Octyl Cyanoacrylate: Quantified Risk for Allergic Contact Dermatitis.

Daniel S Rouhani1, Paul M Villalobos2, Steven Zeng3

  • 1Department of Surgery, Division of Plastic and Reconstructive Surgery, University of California San Francisco, San Francisco, California, USA.

Contact Dermatitis
|February 16, 2026
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Summary

2-octyl-cyanoacrylate-mesh systems release formaldehyde above safe limits, posing risks for skin and respiratory exposure. This byproduct may trigger allergic reactions in sensitized individuals, especially with prior exposure to similar adhesives.

Keywords:
Dermabond Prineoallergic contact dermatitiscyanoacrylateformaldehydeskin adhesives

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Area of Science:

  • Dermatology
  • Toxicology
  • Surgical Materials Science

Background:

  • 2-octyl-cyanoacrylate-mesh systems are utilized for topical wound closure in surgical settings.
  • These devices are increasingly linked to allergic and irritant contact dermatitis.
  • Formaldehyde, a known sensitizer and degradation byproduct, is suspected but unquantified in these reactions.

Purpose of the Study:

  • To quantify formaldehyde emissions from 2-octyl-cyanoacrylate-mesh systems.
  • To assess potential dermal and respiratory exposure risks in clinical settings.
  • To compare formaldehyde levels against established safety benchmarks.

Main Methods:

  • A bench microchamber study quantified formaldehyde off-gassing from the mesh systems over 2 hours.
  • High-performance liquid chromatography with ultraviolet detection (HPLC-UV) was used for quantification.
  • Data were extrapolated to simulate 14-day clinical use under various flux scenarios.

Main Results:

  • Dermal formaldehyde loads at 14 days (8.4 μg/cm²) exceeded the EPA benchmark (1 μg/cm²) and the elicitation range for sensitive patients.
  • Even under reduced flux conditions, dermal exposure (4.8 μg/cm²) remained significantly above the EPA benchmark and elicitation threshold.
  • Mean airborne formaldehyde concentrations (0.020-0.0385 ppm) surpassed the NIOSH limit (0.016 ppm).

Conclusions:

  • 2-octyl-cyanoacrylate-mesh systems emit formaldehyde at levels that exceed sensitization and inhalation thresholds.
  • Concerns exist for significant dermal and respiratory exposure, particularly for individuals with prior sensitization.
  • Previous sensitization to adhesives like nail or super glues may increase the risk of adverse reactions.