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Keywords = profragrances

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12 pages, 4302 KiB  
Article
Controlled Lactonization of o-Coumaric Esters Mediated by Supramolecular Gels
by Fabia Cenciarelli, Giuseppe Falini, Demetra Giuri and Claudia Tomasini
Gels 2023, 9(4), 350; https://doi.org/10.3390/gels9040350 - 21 Apr 2023
Cited by 6 | Viewed by 2218
Abstract
Fragrances are volatile organic compounds widely used in our daily life. Unfortunately, the high volatility required to reach human receptors reduces their persistency in the air. To contrast this effect, several strategies may be used. Among them, we present here the combination of [...] Read more.
Fragrances are volatile organic compounds widely used in our daily life. Unfortunately, the high volatility required to reach human receptors reduces their persistency in the air. To contrast this effect, several strategies may be used. Among them, we present here the combination of two techniques: the microencapsulation in supramolecular gels and the use of profragrances. We report a study on the controlled lactonization of four esters derived from o-coumaric acid. The ester lactonization spontaneously occurs after exposure to solar light, releasing coumarin and the corresponding alcohol. To determine the rate of fragrance release, we compared the reaction in solution and in a supramolecular gel and we demonstrated that the lactonization reaction always occurs slower in the gel. We also studied the more suitable gel for this aim, by comparing the properties of two supramolecular gels obtained with the gelator Boc-L-DOPA(Bn)2-OH in a 1:1 ethanol/water mixture in different gelator concentration (0.2% and 1% w/v). The gel prepared with 1% w/v gelator concentration is stronger and less transparent than the other and was used for the profragrances encapsulation. In any case, we obtained a significative reduction of lactonization reaction in gel, compared with the same reaction in solution. Full article
(This article belongs to the Special Issue Recent Advances in Organogels and Their Applications)
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24 pages, 2912 KiB  
Review
Recent Advances in the Preparation of Delivery Systems for the Controlled Release of Scents
by Adrian Saura-Sanmartin and Laura Andreu-Ardil
Int. J. Mol. Sci. 2023, 24(5), 4685; https://doi.org/10.3390/ijms24054685 - 28 Feb 2023
Cited by 9 | Viewed by 5501
Abstract
Scents are volatile compounds highly employed in a wide range of manufactured items, such as fine perfumery, household products, and functional foods. One of the main directions of the research in this area aims to enhance the longevity of scents by designing efficient [...] Read more.
Scents are volatile compounds highly employed in a wide range of manufactured items, such as fine perfumery, household products, and functional foods. One of the main directions of the research in this area aims to enhance the longevity of scents by designing efficient delivery systems to control the release rate of these volatile molecules and also increase their stability. Several approaches to release scents in a controlled manner have been developed in recent years. Thus, different controlled release systems have been prepared, including polymers, metal–organic frameworks and mechanically interlocked systems, among others. This review is focused on the preparation of different scaffolds to accomplish a slow release of scents, by pointing out examples reported in the last five years. In addition to discuss selected examples, a critical perspective on the state of the art of this research field is provided, comparing the different types of scent delivery systems. Full article
(This article belongs to the Special Issue Feature Papers in 'Physical Chemistry and Chemical Physics' 2023)
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23 pages, 4351 KiB  
Article
Release of Volatile Cyclopentanone Derivatives from Imidazolidin-4-One Profragrances in a Fabric Softener Application
by Serge Lamboley, Basile Vuichoud, Jean-Yves de Saint Laumer and Andreas Herrmann
Molecules 2023, 28(1), 382; https://doi.org/10.3390/molecules28010382 - 2 Jan 2023
Cited by 1 | Viewed by 2582
Abstract
Imidazolidin-4-ones were investigated as hydrolytically cleavable profragrances to increase the long-lastingness of perfume perception in a fabric softener application. The reaction of different amino acid amides with 2-alkyl- or 2-alkenylcyclopentanones as the model fragrances to be released afforded the corresponding bi- or tricyclic [...] Read more.
Imidazolidin-4-ones were investigated as hydrolytically cleavable profragrances to increase the long-lastingness of perfume perception in a fabric softener application. The reaction of different amino acid amides with 2-alkyl- or 2-alkenylcyclopentanones as the model fragrances to be released afforded the corresponding bi- or tricyclic imidazolidin-4-ones as mixtures of diastereoisomers, which were separated by column chromatography. In polar solution, the different stereoisomers equilibrated under thermodynamic conditions to form mixtures with constant isomeric distributions, as shown by NMR spectroscopy. Dynamic headspace analysis on dry cotton demonstrated the controlled fragrance release from the precursors in practical application. Under non-equilibrium conditions (continuous evaporation of the fragrance) and depending on the structure and stereochemistry of the profragrances, the recorded headspace concentrations of the fragrance released from the precursors increased by a factor of 2 up to 100 with respect to the unmodified reference. Prolinamide-based precursors released the highest amount of fragrance and were thus found to be particularly suitable for prolonging the evaporation of cyclopentanone-derived fragrances on a dry cotton surface. Full article
(This article belongs to the Section Natural Products Chemistry)
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10 pages, 7987 KiB  
Article
Controlled Hydrolysis of Odorants Schiff Bases in Low-Molecular-Weight Gels
by Gloria Nicastro, Louise Mary Black, Paolo Ravarino, Simone d’Agostino, Davide Faccio, Claudia Tomasini and Demetra Giuri
Int. J. Mol. Sci. 2022, 23(6), 3105; https://doi.org/10.3390/ijms23063105 - 13 Mar 2022
Cited by 15 | Viewed by 4261
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Biomolecule-Based Biomaterials and Their Application in Drug Delivery Systems)
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20 pages, 950 KiB  
Article
Controlled Release of Damascone from Poly(styrene-co-maleic anhydride)-based Bioconjugates in Functional Perfumery
by Damien L. Berthier, Nicolas Paret, Alain Trachsel, Wolfgang Fieber and Andreas Herrmann
Polymers 2013, 5(1), 234-253; https://doi.org/10.3390/polym5010234 - 22 Feb 2013
Cited by 12 | Viewed by 12443
Abstract
Poly(styrene-co-maleic anhydride)s were modified with poly(propylene oxide (PO)-co-ethylene oxide (EO)) side chains (Jeffamine®) with different EO/PO molar ratios, varying between 0.11 and 3.60. These copolymers were then further functionalized with a β-mercapto ketone of δ-damascone. [...] Read more.
Poly(styrene-co-maleic anhydride)s were modified with poly(propylene oxide (PO)-co-ethylene oxide (EO)) side chains (Jeffamine®) with different EO/PO molar ratios, varying between 0.11 and 3.60. These copolymers were then further functionalized with a β-mercapto ketone of δ-damascone. The obtained poly(maleic acid monoamide)-based β-mercapto ketones were then studied as delivery systems for the controlled release of δ-damascone by retro 1,4-addition. The release of δ-damascone, a volatile, bioactive molecule of the family of rose ketones, was studied by dynamic headspace analysis above a cotton surface after deposition of a cationic surfactant containing fabric softening formulation, as a function of the ethylene oxide (EO)/propylene oxide (PO) molar ratio of the grafted copolymer side chains. The polarity of the EO/PO side chain influenced the release efficiency of the damascone in a typical fabric softening application. PO-rich copolymers and the corresponding poly(styrene-co-maleic anhydride) without Jeffamine® side chains were found to be less efficient for the desired fragrance release than the corresponding bioconjugate with a EO/PO ratio of 3.60 in the side chain. This copolymer conjugate seemed to represent a suitable balance between hydrophilicity and hydrophobicity to favor the release of the δ-damascone and to improve the deposition of the conjugate from an aqueous environment onto a cotton surface. Full article
(This article belongs to the Special Issue Bioconjugates/Biohybrid Polymers)
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