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2 protocols using 3 isopropyl 2 methoxypyrazine

1

Synthesis and Purification of Volatile Compounds

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Isobutyl ITC 97%, 4-pentenyl ITC 95% and sec-butyl ITC 97% were purchased from ABCR (Karlsruhe, Germany), 3-sec-butyl-2-methoxypyrazine from Acros Organics (Geel, Belgium), (3S,3aS,7aR)-wine lactone >95% from Aromalab (Freising, Germany), 2-(methylthio)ethyl ITC >96% from FCH Group (Chernigiv, Ukraine), butanoic acid ≥99% from Fluka (Steinheim, Germany), (Z)-3-hexenal 50% from SAFC (Steinheim, Germany) and 3-methylbutyl ITC >98% from Santa Cruz Biotechnology (Heidelberg, Germany). Acetic acid >99%, AITC 95%, p-anisaldehyde 98%, benzyl ITC 98%, 3-hydroxy-4,5-dimethyl-2(5H)-furanone (sotolone) ≥97%, 3-isobutyl-2-methoxypyrazine ≥99%, 3-isopropyl-2-methoxypyrazine 99%, 2-methylbutanoic acid 98%, 3-methylbutanoic acid 99%, skatole 98%, 3-(methylthio)propanal 98%, 3-(methylthio)propyl ITC 98%, 1-octen-3-one 50%, 2-phenylacetaldehyde 90% and PEITC >99% were purchased from Sigma-Aldrich (Steinheim, Germany) and 3-butenyl ITC 95% from TCI Europe (Eschborn, Germany). CETP was synthesized as described in our previous study (Kroener and Buettner, 2017 (link)).
Dichloromethane (DCM), which was freshly distilled for purification prior to use, and anhydrous sodium sulfate were purchased from VWR International GmbH (Darmstadt, Germany).
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2

Analytical Standards for Volatiles

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(≥97%), (R)-(+)-α-pinene (99%), (1S)-(-)-β-pinene (99%), 3-isopropyl-2-methoxypyrazine (≥97%), nonanal (95%), tridecane (˃95%), and methyl dihydrojasmonate (mixture of cis and trans) were purchased from Sigma Aldrich (St, Louis, MO, USA). Methyl salicylate (97% purity) was purchased from Sigma Aldrich (Steinhelm, Germany), (+)-(2)-carene (97% purity) from Sigma Aldrich (Switzerland) and (-)-trans caryophyllene (99%) from Fluka. For βphellandrene, we used Angelica seed oil containing 89% (S)-(+)-β-phellandrene (SigmaAldrich, Gillingham, Dorset, UK).
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