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Controlled Hydrolysis of Odorants Schiff Bases in Low-Molecular-Weight Gels
Imines or Schiff bases (SB) are formed by the condensation of an aldehyde or a ketone with a primary amine, with the removal of a water molecule. Schiff bases are central molecules in several biological processes for their ability to form and cleave by small variation of the medium. We report here t...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8952255/ https://www.ncbi.nlm.nih.gov/pubmed/35328526 http://dx.doi.org/10.3390/ijms23063105 |
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author | Nicastro, Gloria Black, Louise Mary Ravarino, Paolo d’Agostino, Simone Faccio, Davide Tomasini, Claudia Giuri, Demetra |
author_facet | Nicastro, Gloria Black, Louise Mary Ravarino, Paolo d’Agostino, Simone Faccio, Davide Tomasini, Claudia Giuri, Demetra |
author_sort | Nicastro, Gloria |
collection | PubMed |
description | Imines or Schiff bases (SB) are formed by the condensation of an aldehyde or a ketone with a primary amine, with the removal of a water molecule. Schiff bases are central molecules in several biological processes for their ability to form and cleave by small variation of the medium. We report here the controlled hydrolysis of four SBs that may be applied in the fragrance industry, as they are profragrances all containing odorant molecules: methyl anthranilate as primary amine, and four aldehydes (cyclamal, helional, hydroxycitronellal and triplal) that are very volatile odorants. The SB stability was assessed over time by HPLC-MS in neutral or acidic conditions, both in solution and when trapped in low molecular weight gels. Our results demonstrate that it is possible to control the hydrolysis of the Schiff bases in the gel environment, thus tuning the quantity of aldehyde released and the persistency of the fragrance. |
format | Online Article Text |
id | pubmed-8952255 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-89522552022-03-26 Controlled Hydrolysis of Odorants Schiff Bases in Low-Molecular-Weight Gels Nicastro, Gloria Black, Louise Mary Ravarino, Paolo d’Agostino, Simone Faccio, Davide Tomasini, Claudia Giuri, Demetra Int J Mol Sci Article Imines or Schiff bases (SB) are formed by the condensation of an aldehyde or a ketone with a primary amine, with the removal of a water molecule. Schiff bases are central molecules in several biological processes for their ability to form and cleave by small variation of the medium. We report here the controlled hydrolysis of four SBs that may be applied in the fragrance industry, as they are profragrances all containing odorant molecules: methyl anthranilate as primary amine, and four aldehydes (cyclamal, helional, hydroxycitronellal and triplal) that are very volatile odorants. The SB stability was assessed over time by HPLC-MS in neutral or acidic conditions, both in solution and when trapped in low molecular weight gels. Our results demonstrate that it is possible to control the hydrolysis of the Schiff bases in the gel environment, thus tuning the quantity of aldehyde released and the persistency of the fragrance. MDPI 2022-03-13 /pmc/articles/PMC8952255/ /pubmed/35328526 http://dx.doi.org/10.3390/ijms23063105 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Nicastro, Gloria Black, Louise Mary Ravarino, Paolo d’Agostino, Simone Faccio, Davide Tomasini, Claudia Giuri, Demetra Controlled Hydrolysis of Odorants Schiff Bases in Low-Molecular-Weight Gels |
title | Controlled Hydrolysis of Odorants Schiff Bases in Low-Molecular-Weight Gels |
title_full | Controlled Hydrolysis of Odorants Schiff Bases in Low-Molecular-Weight Gels |
title_fullStr | Controlled Hydrolysis of Odorants Schiff Bases in Low-Molecular-Weight Gels |
title_full_unstemmed | Controlled Hydrolysis of Odorants Schiff Bases in Low-Molecular-Weight Gels |
title_short | Controlled Hydrolysis of Odorants Schiff Bases in Low-Molecular-Weight Gels |
title_sort | controlled hydrolysis of odorants schiff bases in low-molecular-weight gels |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8952255/ https://www.ncbi.nlm.nih.gov/pubmed/35328526 http://dx.doi.org/10.3390/ijms23063105 |
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