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Unsaturated fatty acids react with ROS yielding a variety of important products such as peroxides and chlorohydrins as primary and chain-shortened compounds (e.g., aldehydes and carboxylic acids) as secondary products. These modified fatty acids are either released from phospholipids by phospholipases or oxidatively modified subsequent to their release. There is increasing evidence that oligomeric products are also generated upon these processes. Fatty acid esters of hydroxy fatty acids (FAHFAs) are considered as very important products, but chlorinated compounds may be converted into dimeric and (with smaller yields) oligomeric products, as well. Our review is structured as follows: first, the different types of FFA oligomers known so far and the mechanisms of their putative generation are explained. Industrially relevant products as well as compounds generated from the frying of vegetable oils are also discussed. Second, the different opinions on whether dimeric fatty acids are considered as \u201cfriends\u201d or \u201cfoes\u201d are discussed.<\/jats:p>","DOI":"10.3390\/molecules28237850","type":"journal-article","created":{"date-parts":[[2023,11,30]],"date-time":"2023-11-30T00:34:10Z","timestamp":1701304450000},"page":"7850","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["From Oxidized Fatty Acids to Dimeric Species: In Vivo Relevance, Generation and Methods of Analysis"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4993-5136","authenticated-orcid":false,"given":"Jenny","family":"Leopold","sequence":"first","affiliation":[{"name":"Institute for Medical Physics and Biophysics, Faculty of Medicine, Leipzig University, H\u00e4rtelstr. 16-18, D-04107 Leipzig, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Patricia","family":"Prabutzki","sequence":"additional","affiliation":[{"name":"Institute for Medical Physics and Biophysics, Faculty of Medicine, Leipzig University, H\u00e4rtelstr. 16-18, D-04107 Leipzig, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0611-7042","authenticated-orcid":false,"given":"Kathrin M.","family":"Engel","sequence":"additional","affiliation":[{"name":"Institute for Medical Physics and Biophysics, Faculty of Medicine, Leipzig University, H\u00e4rtelstr. 16-18, D-04107 Leipzig, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4328-8652","authenticated-orcid":false,"given":"J\u00fcrgen","family":"Schiller","sequence":"additional","affiliation":[{"name":"Institute for Medical Physics and Biophysics, Faculty of Medicine, Leipzig University, H\u00e4rtelstr. 16-18, D-04107 Leipzig, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,11,29]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1016\/0891-5849(94)90246-1","article-title":"Reactive oxygen species, chromosome mutation, and cancer: Possible role of clastogenic factors in carcinogenesis","volume":"16","author":"Emerit","year":"1994","journal-title":"Free Radic. 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