1s α pinene

(1S)-(−)-α-Pinene (98 %), (S)-cis-Verbenol (95 %), and dodecane (99 %) were purchased from Sigma-Aldrich, USA. (−)-Linalool (>97 %) and (1S)-(−)-verbenone at a purity of >97 % were obtained from Fluka, Switzerland and stored at 5 °C.

S-tert-butylmercapto-_L-cysteine (Cys(StBu); Sigma-Aldrich, Saint Louis, MO, USA), triphosgene (TCI, purity > 98.0%), (1S)-(-)-α-pinene (TCI, purity > 97.0%), PEG-OH (Sigma-Aldrich, Saint Louis, MO, USA, M_n~5000), methanesulfonyl chloride (MsCl; TCI, purity > 99.0%), triethylamine (Et₃N; TCI, purity > 99.0%), chloroform (Wako, Tokyo, Japan, purity~99.0%), isopropanol (IPA; Wako, purity~98%), hexane (Wako, purity~95%), ammonia solution (Wako, ~28 wt%), 1,2,3,4-tetrahydronaphtalene (tetralin; TCI, purity > 98.0%), _DL-dithiothreitol (DTT; TCI, purity > 98.0%), pyridine (Wako, purity~99.0%), butyric anhydride (TCI, purity > 98.0%), and trifluoroacetic acid (TFA; TCI, purity~98.0%) were used as received. Super-dehydrated tetrahydrofuran (THF; Kanto Chemicals, Tokyo, Japan, purity > 99.5%) and super-dehydrated N,N-dimethylformamide (DMF; Kanto Chemicals, purity > 99.5%) were further purified using a purification column (solvent dispensing system; glass contour; HANSEN & CO., Ltd., London, UK). Water for supplying the solution to the mice was prepared through the process of distillation and deionization using Milli-Q reference (Merck, Rahway, NJ, USA). Lipopolysaccharide (LPS from Escherichia coli O111:B4; Aldrich) was used as received.

The solvent was removed under vacuum to yield 1 mL of the extract, to which gaseous nitrogen and n-tetradecane (78.5 uL) as the internal standard were added. Sample analysis was performed on an Agilent 6890N gas chromatograph (Agilent Technologies, Palo Alto, CA, USA) with a flame ionisation detector. The chromatography column used for purification was a D8-5MS column (J&W Scientific, Folsom, CA, USA) composed of 5% phenylpoly (dimethylsiloxane) (60 m × 0.25 mm × 0.25 µm). The injection was performed in the split mode (30:1), with an injection volume of 2µL [51 ]. (1S)-(−)-α-Pinene (98%), (S)-cis-verbenol (95%), and n-tetradecane (99%) were purchased from Sigma–Aldrich, USA.