An analysis of the relationship between solubility and stimulating effect in tarsal chemoreception

The rejection thresholds of the blowfly Phormia regina Meigen for a selected series of substituted aliphatic hydrocarbons have been determined and an analysis made of the effect on stimulation of increasing the number of like substitutions from one to two, of the interaction of different types of substituent, and of the position of the substituent in the molecule. The order of stimulating efficiency (reciprocal of rejection threshold) of the functional groups which have been studied is: Br > Cl ? CH(3) ? CHO > C=O > OH. There is a consistent decrease in stimulating effect following the introduction of a second hydroxyl group. The introduction of a second C=O has little effect. Introduction of a second halogen is generally followed by a decrease in threshold. Two different species of functional group, one of which tends to increase water solubility and the other to decrease it, tend to counter-balance each other. A single oxygen-containing functional group on the end of the molecule or two of these groups which are terminal reduce the stimulating effect less than when one or more of such groups are subterminal or located elsewhere within the molecule. Branching of the carbon chain decreases effectiveness. Sulfur and oxygen linkages also decrease effectiveness. In general, the length of the free alkyl group largely determines the stimulating effectiveness. Its power is modified to varying degrees by the nature of the attached polar groups. Of all chemical properties examined, solubility alone agrees consistently with the foregoing data. Threshold varies directly with the molar solubility of the compounds in water. The fact that the threshold values for individual compounds are frequently different from those which would be expected solely on the basis of the correlation between threshold and solubility in water suggests that other factors are also concerned in stimulation. These have not yet been identified.