(10E,12E,14E)-9,16-Dioxooctadeca-10,12,14-trienoic acid

Abstract

The title octa­deca­trienoic acid derivative, C18H26O4, was isolated from Silene maritima With. (Caryophyllaceae), the first time this natural compound has been found in the Caryophyllales order. This fatty acid has an 18-carbon backbone with three double bonds on trans (E) conformation and two carbonyl. In the crystal, molecules are linked via pairs of O—H⋯O hydrogen bonds, forming inversion dimers.

Comprehensive Profiling of Macamides and Fatty Acid Derivatives in Maca with Different Postharvest Drying Processes Using UPLC-QTOF-MS

“…A series of cleavages were observed at the conjugated triene structure (C10–C11, C12–C13, and C14–C15), which corresponded to m / z 235 ([M – C 4 H 7 O – H] − ), m / z 209 ([M – C 6 H 9 O – H] − ), m / z 185 ([M – C 4 H 7 O – H] − ), m / z 121 ([M – C 10 H 17 O – H] − ), m / z 97 ([M – C 12 H 17 O 3 – H] − ), and m / z 71 [M – C 14 H 19 O 3 – H] − (Figure A). Compared with the fragmentation pattern of peak 1, peak 2 (Figure B) was the dehydrogenation product of 16-hydroxy-9-oxo-10 E ,12 E ,14 E -octadecatrienoic acid, namely, 9,16-dioxo-10 E ,12 E ,14 E -octadecatrienoic acid . Notably, peaks 1 and 2 were also detected in Maca for the first time.…”

Identification of Desiccation Stress-Inducible Antioxidative and Antiglycative Ultraviolet-Absorbing Oxylipins, Saclipin A and Saclipin B, in an Edible Cyanobacterium Aphanothece sacrum

“…Previously, (10 E ,12 E ,14 E )-9,16-dioxoocta-deca-10,12,14-trienoic acid was isolated from the Caryophyllaceae Silene maritima With. and was determined by X-ray crystallography . However, NMR spectral data for this compound have not yet been reported.…”