Antimicrobial activity of carvacrol related to its chemical structure
Abstract
AIMS: To investigate the relation between the chemical structure and the antimicrobial activity of carvacrol, eugenol, menthol and two synthesized carvacrol derivative compounds: carvacrol methyl ether and carvacryl acetate against bacteria, Escherichia coli, Pseudomonas fluorescens, Staphylococcus aureus, Lactobacillus plantarum, Bacillus subtilis, a yeast Saccharomyces cerevisiae and one fungi Botrytis cinerea. METHODS AND RESULTS: The antimicrobial activity was tested in liquid and vapour phases, by both broth liquid and microatmosphere methods, respectively. The same classification of the compound's antimicrobial efficiency was found with both methods. Eugenol and menthol exhibited a weaker antimicrobial activity than carvacrol, the most hydrophobic compound. Carvacryl acetate and carvacrol methyl ether were not efficient, indicating that the presence of a free hydroxyl group is essential for antimicrobial activity. CONCLUSIONS: The different extents of antimicrobial aroma compounds' efficiency showed that hydrophobicity is an important factor and the presence of a free hydroxyl group and a delocalized system allows proton exchange. SIGNIFICANCE AND IMPACT OF THE STUDY: This study has identified the importance of the hydrophobicity and the chemical structure of phenolic aroma compounds for antimicrobial activity and may contribute to a most rational use of these compounds as antimicrobial agent.
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Carvacrol is more effective than other essential oils, such as p-cymene.
“For example, carvacrol is more effective than other EOs, such as p-cymene [12,18,19].”
From Effect of essential oils on pathogenic bacteria (2013) · cites this paper as [19]
Inhibiting electron transport for energy production and disrupting the proton motive force, protein translocation and synthesis of cellular components are physiological changes that can result in cell lysis and death.
“Inhibiting electron transport for energy production and disrupting the proton motive force, protein translocation and synthesis of cellular components are all physiological changes that can result in cell lysis and death [19,29].”
From Effect of essential oils on pathogenic bacteria (2013) · cites this paper as [19]
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- Authors
- Ben Arfa, A., Combes, S., Preziosi-Belloy, L., Gontard, N., & Chalier, P.
- Affiliations
- Centre National de la Recherche Scientifique (FR)
- Ingénierie des Agropolymères et Technologies Emergentes (FR)
- Corresponding author
- Chalier, P.
- Venue
- Letters in Applied Microbiology
- Publisher
- Oxford University Press (OUP)
- Published
- 2006-08
- Volume
- 43
- Issue
- 2
- Pages
- 149-154
- ISSN
- 0266-8254 (ISSN-L)
- 1365-2673
- OpenAlex
- W2072377626
- Cited by
- 647
- References
- 18
- Citations by year
- 2026: 21 · 2025: 24 · 2024: 41 · 2023: 42 · 2022: 67 · 2021: 63 · 2020: 52 · 2019: 45 · 2018: 35 · 2017: 46 · 2016: 31 · 2015: 27 · 2014: 31 · 2013: 22 · 2012: 30
- FWCI
- 16.62
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Letters in Applied Microbiology (publishedVersion)
- PubMed (publishedVersion)
- HAL (submittedVersion)
- Funders
- Ministère de l'Enseignement Supérieur et de la Recherche
- Topics
- Life Sciences › Agricultural and Biological Sciences › Food Science › Essential Oils and Antimicrobial Activity
- Physical Sciences › Chemistry › Organic Chemistry › Antimicrobial agents and applications
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Keywords
- carvacrol, structure-activity relationship, antimicrobial activity, eugenol, menthol, hydrophobicity, free hydroxyl groups, Escherichia coli, Staphylococcus aureus, Lactobacillus plantarum, Bacillus subtilis, Saccharomyces cerevisiae, Botrytis cinerea
- MeSH terms
- Cymenes, Anti-Infective Agents, Bacteria, Eugenol, Fungi, Gases, Hydroxides, Menthol, Microbial Sensitivity Tests, Phenol, Monoterpenes, Hydrophobic and Hydrophilic Interactions
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