Odor similarities in structurally related odorants

Similarity assessments against one or several references wereused to estimate "earthiness" in 7 pure cyclic alcohols. The "earthy" odor quality of 3 isomers (I, II, IV) of the moldmetabolite "geosmin" (1, 10dimethyl-9-decalol C₁₂H₂₂O) was foundto be present in 2 other alcohols possessing a partial geosminstructure: exo-2-ethyl-fenchol (C₁₁H₂₂O) (V) and cis-cis 2,6-di-methyl-cyclohexanol(C₈H₁₆O) (VI). All have in common an axial hydroxy group attachedto a 5 or 6 carbon ring with alpha methyls on both sides. The trans-cis and trans-trans isomers of 2,6 dimethyl cyclohexanol(VII, VIII) both with equatorial hydroxy groups, were rankedas different from the above group. Instead their odor resemblesmore that of their aromatic precursor — 2,4 dimethyl phenol(IX) — than that of their axial isomer (VI). The two trans-ring geosmin isomers (I,II) and 2-ethylfenchol(V) were still judged earthy at up to 1000x the lowest concentrationtested. However, the cis-ring geosmin isomer (IV) and the axial cyclohexanol(VI) were perceived by most subjects to change in quality: earthyat lower concentrations but increasingly different at higherones. Discrimination between earthy odorants decreased with decreasingconcentration. Geosmins I, IV and 2 ethyl-fenchol (V) were particularlyconfused. However, discrimination did not appear to be affectedby prior adaptation to geosmin IV. Subjects appeared to be able to focus on the earthy odor qualitycomponent in single odorants IV, V, VI in which several otherquality components could be discerned as well.