77388-16-0

Synthetic route

diazomethane (186581-53-3, 908094-01-9) + (7'Z,10'Z,13'Z)-hexadeca-7,10,13-trienoic acid (2271-35-4, 7561-64-0) → (Z,Z,Z)-7,10,13-hexadecatrienoic acid methyl ester (77388-16-0)

(2S)-1-O-(7Z,10Z,13Z)-hexadecadienoyl-2-O-(7Z,10Z)-hexadecadienoyl-3-O-β-D-galactopyranosyl-sn-glycerol → (7Z",10Z")-hexadecadienoic acid methyl ester (18829-90-8) + (Z,Z,Z)-7,10,13-hexadecatrienoic acid methyl ester (77388-16-0) + (2R)-1-O-β-D-galactopyranosylglycerol (16232-91-0)

Conditions	Yield
With sodium methylate In methanol for 0.166667h; Ambient temperature;	A n/a B n/a C 1.7 mg

(2S)-1-O-(7Z,10Z,13Z)-hexadecadienoyl-2-O-(7Z,10Z)-hexadecadienoyl-3-O-β-D-galactopyranosyl-sn-glycerol → (Z,Z,Z)-7,10,13-hexadecatrienoic acid methyl ester (77388-16-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: Lipase type XI, Triton X-100, boric acid-borax buffer, pH 7.7 / 1 h / 38 °C View Scheme

1-O-(ω5Z)-etherolenoyl-2-O-(7Z,10Z,13Z)-hexadecatrienoyl-3-O-β-D-galactopyranosyl-sn-glycerol + sodium methylate (124-41-4) → (9Z,11E,1'Z,3'Z)-12-(1',3'-hexadienyloxy)-9,11-dodecadienoic acid methyl ester (151675-37-5) + (Z,Z,Z)-7,10,13-hexadecatrienoic acid methyl ester (77388-16-0)

Conditions	Yield
In methanol

Upstream product

• 124-41-4 sodium methylate 
• 186581-53-3 diazomethane 
• 2271-35-4 (7'Z,10'Z,13'Z)-hexadeca-7,10,13-trienoic acid 

Relevant academic research and scientific papers

Detection and identification of complex oxylipins in meadow buttercup (Ranunculus acris) leaves

Screening of linolipins, i.e. galactolipids containing esterified residues of divinyl ether oxylipins, in the leaves of several higher plants revealed the presence of these complex oxylipins in the meadow buttercup leaves. The rapid accumulation of linoli