{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,7]],"date-time":"2026-09-07T20:16:49Z","timestamp":1788812209465,"version":"build-2803163510"},"reference-count":51,"publisher":"MDPI AG","issue":"14","license":[{"start":{"date-parts":[[2024,7,21]],"date-time":"2024-07-21T00:00:00Z","timestamp":1721520000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Utilizing Density Functional Theory (DFT) calculations at the B3LYP\/QZVP level and incorporating the Conductor-like Polarizable Continuum Model (C-PCM) for solvation, the thermodynamic and chemical activity properties of 21-(hydroxymethoxy)henicosadecaenal, identified in cultured freshwater pearls from the mollusk Hyriopsis cumingii, have been elucidated. The study demonstrates that this compound releases formaldehyde, a potent antimicrobial agent, through dehydrogenation and deprotonation processes in both hydrophilic and lipophilic environments. Moreover, this polyenal exhibits strong anti-reductant properties, effectively scavenging free radicals. These critical properties classify the pearl-derived ingredient as a natural multi-functional compound, serving as a coloring, antiradical, and antimicrobial agent. The 2-(hydroxymethoxy)vinyl (HMV) moiety responsible for the formaldehyde release can be transferred to other compounds, thereby enhancing their biological activity. For instance, tyrosol (4-(2-hydroxyethyl)phenol) can be modified by substituting the less active 2-hydroxyethyl group with the active HMV one, and hinokitiol (4-isopropylotropolone) can be functionalized by attaching this moiety to the tropolone ring. A new type of meso-carrier, structurally modeled on pearls, with active substances loaded both in the layers and the mineral part, has been proposed.<\/jats:p>","DOI":"10.3390\/molecules29143414","type":"journal-article","created":{"date-parts":[[2024,7,22]],"date-time":"2024-07-22T14:45:53Z","timestamp":1721659553000},"page":"3414","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Enhancing Bioactivity through the Transfer of the 2-(Hydroxymethoxy)Vinyl Moiety: Application in the Modification of Tyrosol and Hinokitiol"],"prefix":"10.3390","volume":"29","author":[{"given":"Marcin","family":"Molski","sequence":"first","affiliation":[{"name":"Department of Quantum Chemistry, Faculty of Chemistry, Adam Mickiewicz University of Pozna\u0144, ul. Uniwersytetu Pozna\u0144skiego 8, 61-614 Pozna\u0144, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,7,21]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Kouassi, M.-C., Grisel, M., and Gore, E. (2022). Multifunctional active ingredient-based delivery systems for skincare formulations: A review. Colloids Surf. B Biointerfaces, 217.","DOI":"10.1016\/j.colsurfb.2022.112676"},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Molski, M. (2024). Density functional theory studies on the chemical reactivity of allyl mercaptan and its derivatives. Molecules, 29.","DOI":"10.3390\/molecules29030668"},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Molski, M. (2024). Theoretical insight into psittacofulvins and their derivatives. 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