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Published on: December 10, 2019
Marine fragrance chemistry
Helmut M Hügel1, Britta Drevermann, Anthony R Lingham
1School of Applied Sciences (Chemistry), RMIT University, GPO Box 2476V, Melbourne, Victoria 3001, Australia. helmut.hugel@rmit.edu.au
Marine fragrances, like Calone 1951, rely on a 7-alkyl group for their characteristic scent. Modifying the polar group alters odor profiles, highlighting the importance of molecular structure in marine fragrance discovery.
Area of Science:
- Organic Chemistry
- Olfactory Science
- Fragrance Chemistry
Background:
- Calone 1951 is a key molecule for marine scents in perfumery.
- Previous research extended the carbon chain of Calone 1951 to enhance marine fragrance.
- The role of the polar group in benzodioxepinone derivatives was not fully understood.
Purpose of the Study:
- Investigate the impact of modifying the polar group of benzodioxepinone on marine fragrance.
- Analyze how aromatic ring substituents affect the olfactory properties of benzodioxepinones.
- Understand the structure-odor relationship for marine fragrances.
Main Methods:
- Synthesized novel benzodioxepinone analogues with chemical modifications or removal of the CO group.
- Performed olfactory evaluations of the synthesized compounds.
- Developed a new synthesis route for diverse aromatic ring substituents.
Main Results:
- Modification or removal of the CO group introduced aldehydic, sweet, and floral-fruity notes, diminishing marine odor potency.
- A 7-alkyl group was found to be essential for maintaining the marine odor characteristic.
- Odorant structure in the hydrophobic binding pocket is crucial for potent marine fragrances.
Conclusions:
- The 7-alkyl group is critical for the marine scent of Calone 1951.
- Molecular modifications near the polar group can alter fragrance profiles, reducing marine notes.
- Understanding the interaction with olfactory receptors is key for designing new marine fragrances.
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