Preparation
A solution of linoleoyl chloride prepared from linoleic acid (2 mmol) and oxalyl chloride (3 mmol) in dichloromethane (5 mL), as described above, was added dropwise to a stirred solution of 3 (1 mmol) in pyridine (5 mL) at room temperature. The reaction mixture was stirred for 1 h at room temperature and then processed as already described. The crude product was subjected to SiO₂ column chromatography by elution with n-hexane/ethyl acetate (20:1, vol/vol) to yield OLP (6) as a colorless oil (0.70 g, 82%). ¹H NMR (CDCl₃, δ): 0.86–0.90 (m by three overlapping triplets, 9H, –CH₃), 1.25–1.62 (m, 64H, –CH₂–), 2.01–2.07 (m, 8H, –C=C–CH₂–), 2.31 (t, J = 6.4 Hz, 6H, –OCO–CH₂–), 2.77 (t, J = 5.5 Hz, 2H, –C=C–CH₂–C=C–), 4.14 (dd, J = 12.2 and 6.3 Hz, 2H, 1- and 3-H), 4.28 (dd, J = 12.2 and 4.4 Hz, 2H, 1- and 3-H), 5.27 (m, 1H, 2-H), and 5.34 ppm (m, 6H, –CH=CH–). ¹³C NMR (CDCl₃, δ): 62.07 (glyceryl C1 and C3), 68.86 (glyceryl C2), 87.11 (–CH–OOH–), 127.86, 128.05, 129.69, 129.97, 129.99, 130.21 (–C=C–), 172.82, and 173.25 ppm (–COO–).
References
[1] Hui, S.-P., Murai, T., Yoshimura, T., Chiba, H., & Kurosawa, T. (2003). Simple chemical syntheses of TAG monohydroperoxides.
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38 12, 1287–1292.
https://doi.org/10.1007/s11745-003-1191-9[2] Awl, R. A., Frankel, E. N., & Weisleder, D. (1989). Synthesis and characterization of triacylglycerols containing linoleate and linolenate†.
Lipids,
24 10, 866–872.
https://doi.org/10.1007/BF02535761
