We also studied other alcohols with energetic centers in their nonpolar group. From various ethenic fatty acids, we prepared the corresponding alcohols by reducing the carboxyls to primary alcohols through treatment with lithium aluminum hydride. Thus we obtained, in addition to oleic alcohol, linoleic and ricinoleic alcohols for the nonconjugated fatty acids and eleostearic alcohol for the conjugated members, as well as the corresponding alcohols of an entire series of mixtures of fatty acids from saf flower oil, cotton seed oil, cod liver oil, acid lipids of organs, etc., and of conjugated fatty acids derived from them. Having two series of substances with the same common nonpolar group, but with different polar groups, COOH and OH, we could relate the effect of these alcohols to their respective fatty acids and thus ascertain once more the fundamental role played by the polar and nonpolar groups in determining the biological effects of lipoids.

Study of the effects induced upon skin viral infection has largely helped to define the differences. The polar group determines the direction of the intervention—increased receptivity or refractivity—but the extent of intervention is determined by the nonpolar group. For example, the effect is very much reduced for oleic and even for linoleic alcohols and it was similarly reduced, in the opposite direction, for the respective acids. Effects were more apparent for polyunsaturated alcohols, ricinoleic and eleostearic alcohols, polyconjugated members and corresponding acids.

The same antagonism between the corresponding acids and alcohols was very clear for systemic analyses, pain, healing of wounds, and effects upon tumors. The extent of the effects in either direction is generally determined by the nature of the nonpolar group and its energetic centers.

This comparative study of acids and alcoholic lipoids has permitted us to arrive at an important conclusion concerning the general behavior of lipoids. Thus, while the nonpolar group is extremely important for the extent of the changes induced, it appears to be secondary in importance to the polar group which determines the direction of the changes. And this explains the role attributed to the polar group in the biological activity of these agents and their separation into two fundamental groups with antagonistic biological properties, which is the basis of our approach to lipoids.

We studied the effects of alcohols and mixtures of polyunsaturated non conjugated and polyconjugated fatty alcohols on a larger scale. These preparations were obtained from safflower and cod liver oil. The immediate effect upon alkaline pain was nearly complete relief. With prolonged treatment, the relief persisted in most cases. No influence upon tumors was noted in most experiments in animals. In humans, tumor arrest in a few cases was obtained. The effect was more accentuated than with isolated members such as eleostearic, linoleic or oleic alcohols. The convulsant effect was much lower than for any other lipoalcohol of this group; even large doses did not produce convulsions except in patients who previously had had convulsions. Effects upon systemic analyses were the same as for most of the higher alcohols, manifest especially upon urinary surface tension and sulfhydryl index. The polyconjugated alcohol mixture, as an agent acting at the systemic level, produced euphoria but had very little effect upon growth and evolution of tumors.

With the intention of lowering the level at which alcohols would act, we studied a special group characterized by having a double bond between C2 and C3. We were particularly interested in two members of this series, allyl and crotyl alcohols.

Other Alcohols

Crotyl alcohol is a lipoid since it is miscible with neutral solvents and only slightly soluble in water. Allyl alcohol, soluble both in water and neutral solvents, appears to be an intermediary substance. Since the 1% solution of crotyl alcohol in saline was painful when given by intramuscular injection, an oily 2% solution was used. No marked differences from the effects of previously discussed lipoalcohols were seen.

We studied polyalcohols having, in addition to a primary alcohol, one or more OH attached to the molecule, such as 9.10-dihydroxy stearic alcohol. However, this substance did not show any properties other than those noted for oleic alcohol. The alcohol obtained from ricinoleic acid, in which the carboxyl was reduced to a primary alcohol, showed a limited systemic effect. Even in larger doses, the changes were slow and not intensive, although passages from one pattern to the other could be seen more often than with other higher alcohols. A state of euphoria appeared in some subjects. The immediate effect upon pain was less than that obtained with other alcohols but, in many instances, was satisfactory. There was no favorable effect upon growth or persistence of tumors in animals or humans. In several cases, on the contrary, rapid growth of the tumor occurred despite lack of pain and even sensations of well being. In general, ricinoleic alcohol seems to act at the interstitial level and above, but not below.