Isocampholenic acid derivatives as potential fragrances

Ciber, Luka (author), Koželj, Tjaša (author), Prosenak, Kaja (author), Petek, Nejc (author), Požgan, Franc (author), Svete, Jurij (author), Štefane, Bogdan (author), Grošelj, Uroš (author)

(+)-Isocampholenic acid, prepared in two steps from (1S)-(+)-10-camphorsulfonic acid in 60% yield (on a scale of 172 mmol), served as the starting compound for the synthesis of small libraries of isocampholenic acid derivatives, comprising a total of 60 compounds, which are of interest due to their olfactory properties. Although isocampholenic acid derivatives are thermodynamically up to 5.9 kcal/mol less stable than endocyclic alkene isomers according to DFT calculation, only minor (up to 2%) isomerization to α-campholenic acid isomers was observed in most cases. The products were fully characterized, and their odor properties were preliminarily assessed by untrained laypersons. This study represents the first systematic exploration of the chemical space of isocampholenic acid. Novel derivatives with distinct odor profiles were discovered, and promising directions for future functionalization for fragrance development were identified.

• Language: English
• Keywords: isokampholenic acid, campholenic acid, DFT calculation, odor propertieses, esters, ethers, enones, ketones, alcohols, cyclopropanation
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2025
• Number of pages: 34 str.
• Numbering: Vol. 30, iss. 18, art. 3794
• PID: 20.500.12556/RUL-175433
• UDC: 547.599
• ISSN on article: 1420-3049
• DOI: 10.3390/molecules30183794
• COBISS.SI-ID: 254590467
• Publication date in RUL: 27.10.2025

Record is a part of a journal

• Title: Molecules
• Shortened title: Molecules
• Publisher: MDPI
• ISSN: 1420-3049
• COBISS.SI-ID: 18462981

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.

Secondary language

• Language: Slovenian
• Keywords: izokamfolenska kislina, kamfolenska kislina, DFT kalkulacije, lastnosti vonja, estri, etri, enoni, ketoni, alkoholi, ciklopropaniranje

Projects

• Funder: ARIS - Slovenian Research and Innovation Agency
• Project number: P1-0179-2020
• Name: Napredna organska sinteza in kataliza