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.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8952255 | PMC |
| http://dx.doi.org/10.3390/ijms23063105 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Hydrogel formed in situ through Schiff base reaction between gallic acid-grafted soybean protein isolate and oxidized dextran: Interactions, physicochemical properties, and digestive characteristics.
Food Chem
January 2025
College of Food Science, Northeast Agricultural University, Harbin, Heilongjiang 150030, China. Electronic address:
Herein, we developed multifunctional hydrogels formed between soybean protein (SPI)-gallic acid conjugate and oxidized dextran (ODex) via a Schiff base reaction. The effects of ODex on the morphology, structure, and functional properties of the hydrogels were elucidated. The results showed that the crosslinking modes in the hydrogels include hydrogen bonding, Schiff bases, Michael addition, and π-π stacking.
View Article and Find Full Text PDFDual EGFR and telomerase inhibitory potential of new triazole tethered Schiff bases endowed with apoptosis: design, synthesis, and biological assessments.
RSC Med Chem
December 2024
Department of Pharmaceutical Chemistry, College of Pharmacy, The University of Mashreq Baghdad 10023 Iraq.
Many cancers have displayed resistance to chemotherapeutic drugs over the past few decades. EGFR has emerged as a leading target for cancer therapy inhibiting tumor angiogenesis. Besides, studies strongly suggest that blocking telomerase activity could be an effective way to control the growth of certain cancer cells.
View Article and Find Full Text PDFA new hydrated crystalline form of -[()-(4-hy-droxy-phen-yl)methyl-idene]-1-1,2,4-triazol-3-amine and its anti-fungal activity.
Acta Crystallogr E Crystallogr Commun
January 2025
Synchrotron SOLEIL, L'Orme des Merisiers, BP48, Saint Aubin, 91192, Gif-sur-Yvette, France.
The synthesis, crystal structure, Hirshfeld analysis, and anti-fungal assessment of a new monohydrated Schiff base with a triazole moiety are reported. The structural study revealed the presence of three significant hydrogen bonds (N-H⋯N, O-H⋯N, and O-H⋯O), which contribute to the cohesion of the crystal. These bonds generate two-dimensional layers parallel to the plane, built on the basis of rings with the graph-set motifs (8) and (24).
View Article and Find Full Text PDFA New Heteroleptic Zn(II) Complex with Schiff Bases Sensitizes Triple-Negative Breast Cancer Cells to Doxorubicin and Paclitaxel.
Pharmaceutics
December 2024
Laboratory of Genetics and Biotechnology, Institute of Biotechnology, Federal University of Uberlândia, Patos de Minas 38700-002, MG, Brazil.
: Triple-negative breast cancer (TNBC) is the most challenging molecular subtype of breast cancer (BC) in clinical practice, associated with a worse prognosis due to limited treatment strategies and its insensitivity to conventional drugs. Zinc is an important trace element for homeostasis, and its Schiff base metal complexes have shown promise in treating advanced tumors. In this study, four new heteroleptic Zn(II) complexes (-) with Schiff bases were synthesized, characterized, and evaluated for their activity in BC cells.
View Article and Find Full Text PDFInhibitory Effects of Sulfur Derivatives on Cell Viability and Secreted Acid Phosphatase In Vitro.
Microorganisms
December 2024
Department of Chemistry, Illinois State University, Normal, IL 61790, USA.
Sulfonamide drugs were the original class of antibiotics, demonstrating the antibacterial potential of dithiocarbazate and thiosemicarbazone Schiff base derivatives of syringaldehyde and 4-hydroxy-3,5-dimethylbenzaldehyde. We synthesized unique Schiff bases via the condensation of the aldehydes with hydrazine derivatives, which allows for the easy synthesis of several related compounds. These Schiff base derivatives were tested for antileishmanial properties against the parasitic protozoan .
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!