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6 protocols using pentacosane

1

Synthesis and Characterization of Long-Chain Alkanes

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Chemical standards of tricosane (99%) and pentacosane (99%) were purchased from Sigma-Aldrich Inc. (St. Louis, MO, USA) and BeanTown Chemical (Hudson, NH, USA), respectively. Hexacosane (99%) and heptacosane (99%) were obtained from Alfa Aesar (Ward Hill, MA, USA). (6Z,9Z)-heptadeca-6,9-diene was synthesized as described above.
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2

Alkane Compounds Acquisition and Characterization

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Heptane (99%), nonane (99%), undecane (≥99%), dodecane (99%), tridecane (≥99%), tetradecane (≥99%), pentadecane (≥99%), hexadecane, heptadecane (99%), octadecane (99%), nonadecane (99%), eicosane (99%), heneicosane (≥99.5%), docosane (99%), tricosane (99%), tetracosane (99%), pentacosane (99%), hexacosane (99%), octacosane (99%), and triacontane (99%) were purchased from Sigma-Aldrich (Darmstadt, Germany). Octane (98%) and decane (≥99%) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Acetone and hexane were of HPLC grade and purchased from Elite Advanced Materials Sdn. Bhd. (Selangor, Malaysia). Ultrapure water (18.2 MΩ cm−1) was purified by a Millipore Milli-Q system (Bedford, MA, USA).
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3

Volatile Organic Compounds Attracting T. pretiosum

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The response of T. pretiosum was verified by mixing the following compounds obtained from Sigma-Aldrich (Gillingham, UK): linalool (97%), hexan-2-ol (99%), 4hydroxy-4-methylpentanone (99%), 6-methyl-5-hepten-2one (99%), nonanal (95%), decanal (98%), octadecanal (99%), nonanoic acid (99%), benzoic acid (99.5%), eicosane (99%), heneicosane (98%), dodecosane (99%), tetracosane (99%), pentacosane (99%), hexacosane (99%), heptacosane (99%), octadecane (99%), nonacosane (99%), (Z)-9-tetradecenyl acetate (Z9-14 OAC) (97%), and (Z)-11-hexadecenyl acetate (Z11-16 OAC) (95%). The total mixture (TM) was made using all compounds except the acetates at the same concentration (0.01 lg ll À1 ) in equal amounts. The TM volume tested was 10 ll contrasted with the same solvent hexane. The responses of T. pretiosum to hexane solutions of Z9-14:OAC or Z11-16 OAC, at concentrations of 1, 0.1, and 0.01 lg ll À1 , in the volume of 10 ll were compared with hexane (10 ll).
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4

Volatile Organic Compounds Attracting T. pretiosum

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The response of T. pretiosum was verified by mixing the following compounds obtained from Sigma-Aldrich (Gillingham, UK): linalool (97%), hexan-2-ol (99%), 4hydroxy-4-methylpentanone (99%), 6-methyl-5-hepten-2one (99%), nonanal (95%), decanal (98%), octadecanal (99%), nonanoic acid (99%), benzoic acid (99.5%), eicosane (99%), heneicosane (98%), dodecosane (99%), tetracosane (99%), pentacosane (99%), hexacosane (99%), heptacosane (99%), octadecane (99%), nonacosane (99%), (Z)-9-tetradecenyl acetate (Z9-14 OAC) (97%), and (Z)-11-hexadecenyl acetate (Z11-16 OAC) (95%). The total mixture (TM) was made using all compounds except the acetates at the same concentration (0.01 lg ll À1 ) in equal amounts. The TM volume tested was 10 ll contrasted with the same solvent hexane. The responses of T. pretiosum to hexane solutions of Z9-14:OAC or Z11-16 OAC, at concentrations of 1, 0.1, and 0.01 lg ll À1 , in the volume of 10 ll were compared with hexane (10 ll).
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5

Hydrocarbon Retention Indices for EOs

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For determination of the retention indices (RI), the following hydrocarbons were used: octane (≥99%), nonane (99%), decane (≥99%), undecane (≥99%), dodecane (99%), tridecane (≥99%), tetradecane (≥99%), hexadecane (≥99%), heptadecane (99%), octadecane (99%), nonadecane (99%), eicosane (99%), heneicosane (≥99.5%), docosane (99%), tricosane (99%), tetracosane (99%), pentacosane (99%), hexacosane (99%), octacosane (99%), and triacontane (99%) purchased from Merck KGaA (Darmstadt, Germany). Hexane (GC grade) purchased from Thermo Fisher Scientific GmbH (Bremen, Germany) was used for dilution of the EOs.
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6

Hydrocarbon Retention Index Analysis

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The following hydrocarbons were used to determine the retention indices (RIs): nonane (99%), decane (≥99%), undecane (≥99%), dodecane (99%), tridecane (≥99%), tetradecane (≥99%), hexadecane (≥99%), heptadecane (99%), octadecane (99%), nonadecane (99%), eicosane (99%), heneicosane (≥99.5%), tricosane (99%), tetracosane (99%), pentacosane (99%), octacosane (99%), and triacontane (99%), and they were purchased from Merck KGaA (Darmstadt, Germany). GC-grade hexane was used for diluting the essential oils, purchased from Thermo Fisher Scientific GmbH (Bremen, Germany). Fluorescein (3′,6′-dihydroxy-3H-spiro [2-benzofuran-1,9′-xanthen]-3-one) (CAS 2321-07-5), AAPH (2,2′-azobis-(2-methylpropionamidine)-dihydrochloride) (CAS 2997-92-4), and trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid) (CAS 53188-07-1) were purchased from Sigma-Aldrich (Darmstadt, Germany).
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