Frambinone, also known as raspberry ketone or p-hidroxybenzyl acetone, is a volatile phenolic compound that gives raspberries their characteristic scent. In the cosmetic industry it is most commonly used as a fragrance and as a flavour enhancer in the food industry. It is a white powder in the form of translucent white crystals with a sweet fruity smell. Although the literature frequently refers to its potential role in body weight regulation, these claims have not yet been substantiated by reliable scientific evidence. Beyond the presumed metabolic effects, it has also been associated with cardioprotective, antiandrogenic, anti-inflammatory, hepatoprotective and depigmenting properties. Nevertheless, for the majority of these effects, the available evidence remains insufficient and further well-designed studies are required. It can be obtained by chemical synthesis, biosynthesis from raspberries, or biosynthesis in genetically modified organisms such as bacteria and yeast.
As part of the thesis, we synthesized and olfactory evaluated esters, ethers and acetals obtained from the starting compound – frambinone. The synthesis of 5 esters in 5 ethers were carried out on the phenol group, while the synthesis of acetal was carried out on the carbonyl group. The resulting products were isolated by extraction, and the success of the reaction was verified by thin-layer chromatography. The crude products were purified by column chromatography and then analyzed by nuclear magnetic resonance imaging and infrared spectroscopy, which allowed us to determine the suitability of the compounds and the degree of purity of the resulting products.
The synthesized compounds were evaluated olfactorily by performing an odor test. Volunteers assessed the intensity and pleasantness of the compounds and recorded their associations with the perceived odors. Compound 4-(4-allyloxy)phenyl)butan-2-one (sample no. 7) was determined to be the most pleasant, while ethanol (sample no. 4) was rated as the least pleasant. Most samples were rated as having strong odor intensity, while some were rated as having a low to medium intensity. Among the participants' responses to odor associations, sweet and sour odors and the smell of fruit appeared most frequently. Based on the results obtained, we can conclude that synthesized compounds with pleasant odor would be suitable for use as a fragrance in the cosmetic products.
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