Up to now, a large number of odorants could be identified in food or other natural or synthetical matrices, at times even as (undesired) by-products. Two prominent natural sources of odorous substances are fat and polyphenolic substances such as lignin, bringing about structurally diverse, yet potent and characteristic odorants, namely saturated and unsaturated aldehydes and ketones, as well as phenolic substances such as guaiacols. Despite decades of smell research, odor researchers are still in the process of unveiling potent odorants that await discovery both in nature as well as in modern products. However, this endeavor is nowadays more challenging than ever, as compounds with extraordinarily potent smell predominantly remain unknown as they mostly are present at ultra-trace level. To identify and characterize such unknown odor-active compounds, researchers nowadays commonly utilize a strategy of systematic structural design, considering characteristic smell features, formation pathways, and structural cues obtained from trace odorant analysis. Synthesizing a range of structurally modified targets together with determination of absolute odor thresholds in air and odor qualities then supports discovery of characteristic molecular features related to smell. This approach has been used in the present study for the investigation of different homologues series of fatty acid oxidation products as well as guaiacol derivatives. Besides the consideration of structure-odor correlations within this investigation, inter-individual differences in odor perception were taken into account. All analyses of odor thresholds in air and odor qualities were conducted by means of gas chromatography-olfactometry. The first part of the thesis addresses the investigation of odor properties of different homologues series of fatty acid oxidation products, which are partly already known (naturally occurring) odorants. Homologues series of alka-1,5-dien-3-ones, alk-1-en-3-ones, alka-1,5-dien-3-ols, and alk-1-en-3-ols were synthesized, and a total of 47 compounds has been investigated with regard to their odor properties. Thereby showing the successive odor quality change for the series of the alk-1-en-3-ols and alk-1-en-3-ones from pungent via metallic, vegetable-like over mushroom-like to citrus-like, soapy, or herb-like with increasing chain length. Two odor threshold minima were found for the six-carbon and for the eight- and nine-carbon odorants, both for the alkenols as well as the alkenals. For the alkadien-3-ols and their corresponding ketones the odor qualities did not change significantly. They elicit geranium-like, metallic odor impressions with an increasing tendency to a mushroom-like odor with increasing chain length. The lowest thresholds were found for the eight- and nine-carbon (Z)-compounds. 36 compounds of the 48 analyzed (E)- and (Z)-3-unsaturated volatile acids, alcohols, and aldehydes have been synthesized. In the series of (E)- and (Z)-3-alkenoic acids the odor quality changed successively from sweaty via plastic-like to sweaty and waxy. On the other hand, the odor qualities in the series of (E)- and (Z)-3-alken-1-ols, and (E)- and (Z)-3- alkenals changed from grassy, green to an overall citrus-like, fresh, soapy, and coriander-like odor with increasing chain length. Regarding their odor potencies, the lowest thresholds in air were found for (E)-3-heptenoic acid, (E)-3-hexenoic acid, and (E)-3-hexenal, and for (Z)-3-hexenal, (Z)-3-octenoic acid, and (Z)-3-octenal. Overall, the (Z)-3-compounds showed lower odor thresholds in air than the corresponding saturated compounds, which have been analyzed additionally, followed by the (E)-3- compounds. The second part of this thesis deals with the analysis and determination of odor thresholds and odor qualities of different guaiacol derivatives. Guaiacol and its derivatives are found in nature and are known for their typical smells: smoky, clovelike and vanilla-like. All investigated compounds, guaiacol and its alkylated, alkenylated, and methoxylated derivatives (26 compounds in total, 12 synthesized), elicited characteristic smoky/smoked ham-like, vanilla-like/sweet and/or clove-like smell impressions. The odor thresholds of the compounds were generally very low, ranging from 0.00018 to 111 ng/Lair. The lowest thresholds were determined for 5- methoxyguaiacol and guaiacol. Moreover, it could be shown that halogenated guaiacol derivatives likewise exhibit the typical guaiacol-like smells. They are not naturally occurring like their halogen-free companions, but formed during the processing of pulp, for instance, as undesired byproducts. 14 halogenated guaiacol derivatives have been analyzed, with five of them having been synthesized within this study. Overall, the investigated compounds elicited the already mentioned characteristic guaiacol-like smells, namely smoky, sweet, vanilla-like, but also medicinal and plaster-like. Their odor thresholds in air were also very low, ranging from 0.00072 to 23 ng/Lair. The lowest thresholds were found for 5- chloro- and 5-bromoguaiacol. The data collected within this study is intended to support future discovery of these compounds, both in nature as well as modern day-products. Further, the results are important for our general understanding of structure-odor correlations, but also reveal the at times high extent of inter-individual variation in smell perception in humans.