From:  Metrological aspects of a gas-phase DFT/B3LYP quantum-chemical approach to prioritize radical scavenging activity among a group of olive oil phenols
 

ΔBDE values of diverse virgin olive oil phenols calculated at B3LYP/6-311G++(2d,2p)//B3LYP/6-31G level of theory in the gas-phase

Phenol*ΔBDEPH**ΔBDETRPhenol*ΔBDEPH**ΔBDETR
1. 4-Hydroxy-phenylacetic acid1.19.013. Luteolin–8.1–0.2
2. Apigenin1.08.914. 3,4-Dihydroxy-phenylacetic acid–8.3–0.4
3. Oleocanthalic acid0.58.415. Oleaceininc acid–8.5–0.6
4. Hydroxy-pinoresinol–0.37.616. 1-(3’-Methoxy-4’-hydroxy) phenyl-6,7-dihydroxy-chroman–8.7–0.8
5. Acetoxy-pinoresinol–0.47.517. Taxifolin–8.7–0.8
6. 4-Hydroxy-cinnamic acid (p-coumaric acid)–0.57.418. 1-Phenyl-6,7-dihydroxy-chroman–8.8–0.9
7. Pinoresinol–0.77.219. Hydroxytyrosol-linolenate–9.0–1.1
8. Ligstroside aglycone monoaldehyde–0.87.120. Hydroxytyrosol-oleate–9.0–1.1
9. Ligstroside aglycone–0.87.121. 3,4-Dihydroxy-cinnamic acid (caffeic acid)–9.2–1.3
10. Tyrosol acetate–1.26.722. Hydroxytyrosol acetate–10.1–2.2
11. 4-Hydroxy-3-methoxy-cinnamic acid (ferulic acid)–1.26.723. Oleuropein aglycone–9.7–1.8
12. 2-Hydroxy-cinnamic acid (o-coumaric acid)–1.76.224. Oleuropein aglycone monoaldehyde–9.8–1.9
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*BDE phenol: 84.3 (kcal/mol); **BDE Trolox: 76.4 (kcal/mol). The compounds are grouped into those that are expected to be inactive (ΔBDEPH values in bold), those that are expected to be less efficient (ΔBDEPH and TR values non-highlighted) or better hydrogen atom donors than Trolox (ΔBDEPH and TR values highlighted in green)