Analytical Data of Optically Active (Z)-7-Decen-4-Olide and Its Derivatives
1. Analytical data S1-S11
Nuclear magnetic resonance (NMR) spectra were recorded using a JNM-ECA-600 spectrometer (JEOL). The chemical shifts are reported in parts per million with respect to tetramethylsilane as an internal standard, and the coupling constants (J) are quoted in Hz. The structures of all compounds were determined using homonuclear correlation spectroscopy, heteronuclear multiple quantum correlation, and heteronuclear multiple bond correlation NMR techniques. Infrared spectra were obtained using a Fourier-transform infrared (FT-IR) spectrometer (Model 460plus; JASCO Corp., Tokyo, Japan). Field ionization (FI) high-resolution mass spectra were obtained using an AccuTOF GCv 4G instrument (JEOL). The melting points (mp) were recorded using an MP-500D micro-melting-point apparatus (Yanaco Technical Science Co., Ltd., Kyoto, Japan) and were uncorrected. The optical rotations were determined using a P-2000 polarimeter (JASCO). Circular dichroism (CD) spectra were obtained using a J-820 spectropolarimeter (JASCO; 1.0 mm cell) for ethanol solutions.
2. 1H NMR and 13C NMR spectra S12-S47
Nuclear magnetic resonance (NMR) spectra were recorded using a JNM-ECA-600 spectrometer (JEOL).
3. CD spectra S48-S51
Circular dichroism (CD) spectra were obtained using a J-820 spectropolarimeter (JASCO; 1.0 mm cell) for ethanol solutions.
4. Antimicrobial properties S52
The antimicrobial properties of the synthetic odour compounds were assayed using the E. coli ATCC25922 and S. aureus ATCC29213 strains. For the screening assay, 10 μL of a bacterial cell suspension containing 1×105 colony-forming units (CFU) was inoculated into 1 mL of Mueller-Hinton broth (MHB; Becton Dickinson and Company, Sparks, MD, USA) supplemented with a test compound.