Dodecanoic acid

Pure chemicals: 1-octanol; 1-octen-3-ol; hexanal; heptanal; octanal; nonanal; 2-decenal, (E); benzaldehyde; hexanoic acid; octanoic acid; dodecanoic acid; benzene, 1,4-dimethoxy; 2-hexen-1-ol, (E); 2-hexen-1-ol, acetate, (E); 3-heptanone, 2-methyl; acetic acid, pentyl ester; acetic acid, hexyl ester; butanoic acid, methyl ester; butanoic acid, ethyl ester; butanoic acid, butyl ester; hexanoic acid, ethyl ester; linalool; γ-dodecalactone and toluene-d₈ were purchased from Sigma-Aldrich (Madrid, Spain). The analytical standards n-alkanes mixture (C₁₀–C₄₀) for retention index (RI) assessment determination was supplied by Supelco (St. Louis, USA).

Bornyl acetate (99%), camphene (95%), camphor (96%), carvarol (98%), (−)-carveol (95%), (+)-carvone (96%), β-caryophyllene (98.5%), caryophyllene oxide (95%), β-citronellal (95%), citral (95%), 1,8-cineole (99%), p-cymene (99%), decyl chloroformate (97%), dodecanoic acid (98%), β-farnesene (90%), geranyl acetate (97%), geraniol (98%), isopulegol (98%), linalool (97%), limonene (97%), limonene oxide (97%), methyl linolenate (99%), myrcene (90%), myristic acid (99%), palmitic acid (99%), α-phellandrene (85%), α-pinene (98%), pivalic acid (99%), sabinene (75%), α-terpineol (90%), γ-terpinene (97%), 4-terpineol (95%), terpinolene (90%), and tymol (99%) were obtained from Sigma-Aldrich (St. Louis, MO, USA). Achillea millefolium L. flowers, Citrus aurantium L. fruits, Leptospermum petersonii F. M. Bailey leaves, Ruta graveolens L. leaves, and Thymus vulgaris L. leaves were collected from a local store in Chonju, Korea. Sample specimens were authenticated by Jeongmoon Kim at Chonbuk National University, Korea. Essential oils of the five plants were obtained by steam distillation extraction, and finally dried over Na₂SO₄ to extract the pure essential oils (Table 1).

The standards of volatile compounds were purchased from Sigma-Aldrich (St. Louis, MO, USA), including isobutanol, 3-methyl-1-butanol, cis-3-hexen-1-ol, 1-hexanol, heptanol, octanol, phenethyl alcohol, 2,6-nonadien-1-ol, dodecanol, ethyl acetate, isoamyl acetate, ethyl lactate, ethyl hexanoate, ethyl octanoate, diethyl succinate, phenethyl acetate, ethyl decanoate, butanoic acid, hexanoic acid, octanoic acid, dodecanoic acid, octanal, (2e,6z)-2,6-nonadienal, benzaldehyde, furfural, citronellol, linalool, rose oxide, geraniol, nerol, β-damascenone, β-ionone, nerolidol, hexanal, guaiacol, 4-Ethylphenol, and 2-octanol which were used as the internal standard.
Folin–Ciocalteu reagent and sodium chloride were purchased from Beijing Chemical Works (Beijing, China). Potassium hydrogen tartrate were purchased at Kemiou Chemical Reagent Co. (Tianjin, China). Bovine serum albumin was obtained from Asahi Kasei Corporation (Tokyo, Japan). Deionized water (<18 MW resistance) was purified by using a Milli-Q purification system (Molecular, Chongqing, China). Bentonite, soybean protein and potassium metabisulfite were purchased from Lallemand Company (Lallemand, Toulouse, France).

Prior to Gas Chromatography-Mass Spectrometry (GC-MS) analysis, active fractions and commercial decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, and tetradecanoic acid (purity > 98%; Sigma–Aldrich, St. Louis, MI, USA) were methylated and ethylated. Samples (30 mg) were diluted with 10 mL acidified methanol or ethanol (1% sulfuric acid) and stirred for 12 h at room temperature. The product of the reaction was suspended in an aqueous solution of 20% Na₂CO₃ (20 mL) and extracted with CHCl₃ (3×, 20 mL, each one) and the solvent was eliminated under vacuum until dry. These derivatives were stored at 4 °C until use in assays [60 (link)].

Titanium isopropoxide (TIP), sodium dodecylsulphate (SDS), dodecanoic acid (DDA) and dodecylamine (DDAmine) were purchased from Sigma Aldrich and used as received. Dodecylphosphonic acid was prepared by a procedure according to Kosolapoff et al. [55 ,56 ]. Methanol and absolute ethanol were purchased from Acros and used as received. Nitric acid (65%) and NaOH were purchased from Merck.

Ebastine, hydroxyebastine, carboxyebastine, desalkylebastine, hydroxyebastine-d5, carebastine-d5, desalkylebastine-d5, bufuralol, hydroxybufuralol, hydroxybufuralol-d9, repaglinide, 2-despiperidyl-2-amino repaglinide (M1), 3′-hydroxyrepaglinide (M4), bupropion, hydroxubupropion, hydroxybupropion-d5, hydroxytolbutamide, carboxytolbutamide, 1′-hydroxytolbutaminde-d9, 4′-carboxytolbutamide-d9, 4-hydroxyMidazolam, 4-hydroxyMidazolam-d5, 6-hydroxyChlorzoxazone and 12-hydroxydodecanoic-d20 acid were purchased from Toronto Research Chemicals (Toronto, ON, Canada). HydroxyChlorzoxazone-d2 was obtained from TLC PharmaChem (Mississauga, ON, Canada). Midazolam and 1′-hydroxyMidazolam-d4 were purchased from Cerilliant (Round Road, TX, USA). Chlorzoxazone, tolbutamide, dodecanoic acid, β-Nicotinamide-Adenine Dinucleotide Phosphate (NADP), glucose-6-phosphate (G6P), glucose-6-phosphate dehydrogenase (G6PD), dimethyl sulfoxide (DMSO), trishydroxymethylaminomethame (TRIS), and phenylmethanesulfonyl (PMSF) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Ethynediaminetetraacetic acid (EDTA) and dithiothreitol were obtained from Bishop (Burlington, ON, Canada) and from Gibco^®, Life Technologies Ltd. (Eugene, OR, USA), respectively. All other chemicals used were commercially available and were of analytical grade.