Antimicrobial activity of carvacrol related to its chemical structure.
OBJECTIVE
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.


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.


CONCLUSIONS
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.
Ben Arfa
A
A
UMR IATE (Agropolymers Engineering and Emerging Technologies), Université Montpellier II, France.
Combes
S
S
Preziosi-Belloy
L
L
Gontard
N
N
Chalier
P
P
D000890:Anti-Infective Agents / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D000081007:Cymenes; D005054:Eugenol / Q000737:chemistry / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects*; D005740:Gases; D057927:Hydrophobic and Hydrophilic Interactions; D006878:Hydroxides; D008610:Menthol / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D039821:Monoterpenes / Q000737:chemistry* / Q000494:pharmacology*; D019800:Phenol / Q000737:chemistry / Q000494:pharmacology
D000890:Anti-Infective Agents; D000081007:Cymenes; D005740:Gases; D006878:Hydroxides; D039821:Monoterpenes; D008610:Menthol; D019800:Phenol; D005054:Eugenol; C031356:hydroxide ion; C073316:carvacrol