9 12 13 trihome

Most native and deuterated standards for analysis of oxylipins, endocannabinoids, and endocannabinoid-related lipids, including 12-[[(cyclohexylamino)carbonyl]amino]-dodecanoic acid (CUDA) used for recovery calculation purposes, were obtained from Cayman Chemical (Ann Arbor, MI, USA). Only 9,10,13-trihydroxyoctadecenoic acid (TriHOME) and 9,12,13-TriHOME were obtained from Larodan (Malmö, Sweden). Acetonitrile (ACN) and methanol (MeOH) were from Merck (Darmstadt, Germany). Isopropanol was from VWR PROLABO (Fontenay-sous-Bois, France). Acetic acid was purchased from Aldrich Chemical Company, Inc. (Milwaukee, WI, USA). Butylhydroxytoluene (BHT) was from Cayman Chemical (Ann Arbor, MI, USA) and ethylenediaminetetraacetic acid (EDTA) from Fluka Analytical, Sigma-Aldrich (Buchs, Switzerland). Glycerol was from Fischer Scientific (Loughborough, UK). All solvents and chemicals were of HPLC grade or higher and ultrapure water was used (Milli-Q Gradient system, Millipore, Milford, MA, USA).

Eicosanoids and endocannabinoids were purchased from Cayman Chemical (Ann Arbor, USA), with the exception of 12(13)-EpODE, 9,10,13-TriHOME and 9,12,13-TriHOME from Larodan (Solna, Sweden) and LTB₅ from Enzo (Solna, Sweden). Sphingolipids were purchased from Avanti Polar Lipids (Alabaster, USA). A complete list of lipid mediator nomenclature is provided in Additional file 2. Methanol, acetonitrile, isopropanol, acetic and formic acid were of LC-MS grade from Fischer Scientific (Stockholm, Sweden). Ethyl acetate and chloroform were purchased from Sigma-Aldrich (St. Louis, USA).