Sensory evaluation demonstrates distinct cooling effects of D-menthol derivatives, suggesting new spice applications.
Consumers' quest for rich sensory attributes has driven in‐depth research into a new class of potential cooling agents. Herein, with the aim of comprehensive utilisation of by‐products in the L‐menthol industry, D‐menthyl acetate, D‐menthyl ethylene glycol carbonate, and D‐menthyloxyethanol have been synthesised from D‐menthol. Sensory evaluation revealed that D‐menthyl acetate exhibited the most complex aroma, combining minty, sweet, and woody notes, while D‐menthyl ethylene glycol carbonate had a cooling threshold of 2.51 mg/L, close to its L‐isomer (1.91 mg/L). Molecular docking indicated that stereochemical differences led to altered hydrogen bond lengths and hydrophobic interactions, affecting receptor binding. Electrostatic potential analysis further confirmed that D‐isomers had slightly weaker electronegative regions near functional groups, consistent with their milder cooling effects. These findings suggest that D‐menthol derivatives possess distinct cooling and aroma characteristics due to differences in spatial configuration and binding affinity, providing new insights for cooling agent design.
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Liu et al. (2025) studied this question.
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