Figure 10. Oxidization of oleic acid to produce monomeric species, without considering peroxy species.
The first potential oligomer (Figure 11 ), dimer D1 (mono-ester) formed by ring-opening mono-acylation of epoxide M2, was not observed (Figure S19 ). However, species T1, the di-acylated epoxide is consistent with the spectral observations. Presumably, D1 was not present in the oxidized products because it quickly reacts which oleic acid or oxygen to form T1 or fragments (F1, F2). Trimer T1, or even a larger species, is also consistent with DOSY measurements. The oligomer formed by thermal oxidation of oleic acid diffuses eight times slower than extra-virgin olive oil (D = 0.082 x 10-10m2/s ) Table S1 , a tri-acylglycerol (885 g/mol) three times heavier than oleic acid (282 g/mol).