Z 3 hexenyl acetate

Super Q (80/100 mesh) was purchased from Alltech (PA, USA). n-Hexane (95%, for pesticide residue analysis) was purchased from Fisher Scientific (Loughborough, Leicestershire, UK). (Z)-3-Hexenyl acetate (98%) were purchased from Alfa Aesar (Heysham, UK). Limonene (97%), cis-jasmone (92%) and linalool (96%) were purchased from TCI America (Portland, USA). α-Pinene (98%), camphene (90%), 6-methyl-5-hepten-2-one (98%), methyl salicylate (99%), ocimene (90%) (mix of (E) and (Z)-isomers), (E)-caryophyllene (80%), benzothiazole (96%), indole (98%), myrcene (97%), octanal (99%), undecane (99%), tridecane (99%), pentadecane (99%), nonanal (95%) and decanal (98%) were purchased from Sigma Aldrich (Steinheim, Germany). Geranylacetone (96%) was purchased from TCI (Tokyo, Japan). (E,E)-α-Farnesene was synthesized in three steps from isoprene and sulfur dioxide (Hassemer et al. 2016 (link)). (E)-4,8-Dimethyl-1,3,7-nonatriene (DMNT) and (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT) were synthesized from geraniol and (E,E)-farnesol, respectively (Leopold 1990 ).

Authentic samples of the compounds tentatively identified by GC‐MS were purchased for structure confirmation by GC peak enhancement and for behavioural assays. (Z)‐3‐Hexenal (50% solution in triacetin), (E)‐2‐hexenal (99%), p‐cymene (99%), 1,8‐cineole (99%), γ‐terpinene (95%), linalool oxide [2‐(5‐methyl‐5‐vinyltetrahydro‐1‐furyl)‐2‐propanol] (>97%) and (R/S)‐camphor (96%) were obtained from Sigma‐Aldrich (Gillingham, Dorset, UK). (Z)‐3‐Hexen‐1‐ol (98%) and (Z)‐3‐hexenyl acetate (99%) were purchased from Alfa Aesar (Heysham, Lancs, UK), and (Z)‐ocimene (90%) was obtained from Bush Boake Allen (London). 3‐Ethylacetophenone (95%) was obtained from Maybridge (Tintagel, Cornwall, UK). (E)‐Ocimene (95%) was synthesised according to Chou et al.13 (E)‐4,8‐Dimethyl‐1,3,7‐nonatriene (95.6%) was synthesised from geraniol by oxidation to the corresponding aldehyde, followed by Wittig methylenation.14