20.500.12556/RUL-147205 Sinteza 2-alkoksibenzaldehidov in 2-aciloksibenzaldehidov in njihovo vrednotenje z vonjalnim testom Synthesis of 2-alkoxybenzaldehydes and 2-acyloxybenzaldehydes and their olfactory evaluation Salicilaldehid (SA) ali 2-hidroksibenzaldehid je organska aldehidna spojina, ki ima na orto mestu prosto fenolno skupino (-OH). Je brezbarvna do svetlo rumena oljnata tekočina, ki ima pri višjih koncentracijah grenak okus in vonj po mandljih. Ta aromatična spojina je poznana zaradi svoje prijetne dišave in hlapljivosti, zaradi česar jo uporabljajo v proizvodnji parfumov. Poleg tega je zaradi svojih aromatičnih lastnosti primerna za izboljšanje okusa različnih prehrambnih izdelkov in pijač. Deluje tudi fungicidno in larvicidno, kar prispeva k vsestranski uporabi. Pomembno vlogo ima kot reagent pri sintezi kumarina. SA je v naravi prisoten v rastlinah in v izločku ličink listnatega hrošča. Namen diplomske naloge je bila sinteza in olfaktorno vrednotenje 2-alkoksibenzaldehidov in 2-aciloksibenzaldehidov. To so različni lipofilni derivati salicilaldehida s prijetnim vonjem, ki bi jih lahko uporabili kot dišave v kozmetiki. Reakcije estrenja in etrenja smo izvajali na prosti hidroksilni skupini z nukleofilno substitucijo. Potek in uspešnost reakcij smo preverjali s tankoplastno kromatografijo. Surove produkte smo očistili s kolonsko kromatografijo. Nato smo čiste produkte analizirali z uporabo dveh spektroskopskih metod, jedrsko magnetno resonanco in infrardečo spektroskopijo, ki sta potrdili ustreznost spojin. Sledilo je olfaktorno vrednotenje spojin z vonjalnim testom, s katerim so prostovoljci ocenjevali prijetnost vonja, jakost vonja in na kaj jih vonj spominja. Etri, pridobljeni iz salicilaldehida, imajo bolj prijeten vonj v primerjavi z estri. Med vsemi vzorci je najbolj izrazit vonj imel 2-formilfenil acetat, ki je bil izbran tudi kot najbolj neprijeten vonj. Etil 4-(2-formilfenoksi)butanoat je izstopal z najbolj prijetnim vonjem, ki je bil opisan kot sladek, cvetličen in je močno spominjal na vonj parfuma. Salicylaldehyde (SA) or 2-hydroxybenzaldehyde is an organic aldehyde compound with a free phenolic group (-OH) at the ortho position. It is a colorless to light yellow, oily liquid that exhibits an almond-like odor at higher concentrations. This aromatic compound is renowned for its pleasant fragrance and volatility, making it a popular ingredient in perfume production. Additionally, it is suitable for enhancing the taste of various food and beverage products due to its aromatic properties. It also exhibits fungicidal and larvicidal activities contributing to its versatile applications. It plays a significant role as a reagent in the synthesis of coumarin. Salicylaldehyde is naturally present in plants and in the secretion of leaf beetle larvae. The objective of the thesis was the synthesis and olfactory evaluation of 2-alkoxybenzaldehydes and 2-acyloxybenzaldehydes. These are various lipophilic derivatives of salicylaldehyde with pleasant smells which could be utilized as fragrances in cosmetics. Esterification and etherification reactions were performed on the free hydroxyl group through nucleophilic substitution. The progress and success of the reactions were monitored using thin-layer chromatography. The raw products were purified through column chromatography. Subsequently, the pure products were analyzed using two spectroscopic techniques, nuclear magnetic resonance, and infrared spectroscopy, which confirmed the structure of the products. This was followed by an olfactory evaluation of the compounds with an olfactory test, with which the volunteers evaluated the pleasantness of the smell, the strength of the smell, and what the smell reminded them of. Ethers derived from salicylaldehyde have a more pleasant smell compared to esters. Among all the samples, 2-formylphenyl acetate had the most prominent smell, which was also described as the most unpleasant. Ethyl 4-(2-formylphenoxy) butanoate stood out with the most pleasant odor, which was described as sweet, floral, and strongly perfume-like. saliciladehid dišave sinteza kromatografske metode vonjalna analiza salicylaldehyde fragrances essential oils chromatographic methods synthesis olfactory evaluation true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2023-06-25 07:46:05 2023-06-25 07:46:12 2023-06-26 04:00:01 0000-00-00 00:00:00 2023 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 1970-01-01 96284 14333.pdf 14333.pdf 1 AA72E2962595A697842E1534DC40BEBD a5444c4ca77cb850dd5be49d43da10367b1f7d87e154a5ee905be265062781ee 346a2380-131b-11ee-a314-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=170681 Fakulteta za farmacijo 0 0 0