Synthesis and olfactory evaluation of cinnamyl alcohol and cinnamic acid derivatives

Cinamil alkohol in cimetova kislina sta naravni spojini, ki se uporabljata v parfumski in kozmetični industriji ter farmaciji. Najbolj znana je njuna prisotnost v cimetovcu, ki spada v družino lovorovk (Lauraceae). Cinamil alkohol in cimetova kislina sta sestavini eteričnega olja cimeta, ki ga pridobivajo iz listov, lubja in korenin. Pri standardnih pogojih je cinamil alkohol bela do rumenkasta kristalna trdna snov, s prijetnim, cvetličnim in sladkim vonjem ter okusom po cimetu. Cimetova kislina pa je bela kristalna organska spojina, katere vonj spominja na med. V naravi so cimetova kislina in njeni derivati zelo razširjeni, a jih večinoma najdemo v zelo nizkih koncentracijah. Sintezno pridobljena cimetova kislina pa nastaja s Perkinovo reakcijo. Namen diplomske naloge je bil sintetizirati derivate cinamil alkohola in cimetove kisline ter nastale produkte olfaktorno ovrednotiti. Uspešno smo sintetizirali deset njunih derivatov, po strukturi estrov in etrov. Ena reakcija ni potekla. Vse produkte smo očistili s kolonsko adsorpcijsko kromatografijo, kjer smo za razvijanje kromatogramov uporabili mobilno fazo, sestavljeno iz zmesi etilacetata in heksana v volumskem razmerju 1 : 4 ter 1 : 6. Uspešnost reakcij in identiteto produktov smo preverili z instrumentalnimi analiznimi metodami, in sicer z uporabo jedrske magnetne resonance ter infrardeče spektroskopije. Nato smo končne spojine olfaktorno vrednotili z vonjalnim testom, s katerim smo preverjali prijetnost in jakost vonjav ter asociacije na druge vonje. Večina derivatov cinamil alkohola in cimetove kisline ima prijeten vonj. Povprečna ocena jakosti vonjev testiranih vzorcev ima šibek do zmerno močan vonj. Vonji niso bili konstantni in so se tekom vonjalne analize spreminjali. Pri vrednotenju vzorcev so anketiranci označili cinamil butirat, cinamil fenilacetat in cinamil heksileter kot najprijetnejše vonjave. Pri opisovanju vonjav nismo ugotovili nobenih razlik med osebami, ki parfume uporabljajo in tistimi, ki jih ne.Cinnamyl alcohol and cinnamic acid are natural compounds used in the perfume, cosmetics and pharmaceutical industries. They are best known to be found in cinnamon tree, which belongs to the family of laurels (Lauraceae). Cinnamyl alcohol and cinnamic acid are components of cinnamon essential oil, which is extracted from the leaves, bark and roots of cinnamon. Under standard conditions, cinnamyl alcohol is a white to yellowish crystalline solid, with a pleasant, floral and sweet aroma and cinnamon taste. Cinnamic acid is a white crystalline organic compound with an odour reminiscent of honey. Cinnamic acid and its derivatives are widespread in nature, but are mostly found in very low concentrations. Synthetically produced cinnamic acid is produced by the Perkin reaction. The aim of the thesis was to synthesize derivatives of cinnamyl alcohol and cinnamic acid derivatives and and evaluate these products in an olfactory analysis. Ten of their derivatives were successfully synthesised, according to the structure of esters and ethers. One reaction did not proceed. All the products were cleaned by column adsorption chromatography, where chromatograms were developed using a mobile phase consisting of a mixture of ethyl acetate and hexane in volume ratios of 1 : 4 and 1 : 6. The success of the reactions and the identity of the products were verified by instrumental analytical methods, nuclear magnetic resonance and infrared spectroscopy. The final products were then evaluated olfactorially by an odour test, which was used to check the pleasantness and strength of aromas and their associations with other odours. Most derivatives of cinnamyl alcohol and cinnamic acid have a pleasant smell. The average odour strength rating of the tasted samples has a weak to moderately strong odour. The odours were not constant and varied during the odour analysis. When evaluating the samples, respondents indicated cinnamyl butyrate, cinnamyl phenylacetate and cinnamyl hexyl ether as the most pleasant odours. No differences were found between respondents who use perfumes and those who do not