Mandelic - Cyclandelate

The Franke model is a definite improvement as compared to the parabolic model. In many practical cases it gives a much better fit, e.g. eqs. 85 and 86 for the spasmolytic activities of mandelic acid esters (Table 14 RA = relative biological activity values, based on cyclandelate (15), RA = 100%) [345]. 

The name used by Chemical Abstracts for cyclandelate is a-hydroxybenzeneacetic acid, 3,3,5-trimethyl cyclohexyl ester. It is also called mandelic acid, 3,3,5-trimethylcyclohexyl ester 3,3,5-trimethylcyclohexyl mandelate 3,3,5-trimethylcyclohexyl amygdalate and 3,3,5-trimethyl cyclohexanol a-phenyl-a-hydroxyacetate. Trade names include, Cyclospasmol, Natil, Novodil, Perebral, and Spasmocyclon (1). The Chemical Abstracts number is 456-59-7. 

The four isomers which make up cyclandelate arise in the synthesis from the reaction of -mandelic acid with cis-3.3.5-trimethv1cyc1ohexano1 and are described In Table I (taken from Nakamichl (10). ... 

The metabolites of cyclandelate are mandelic acid, phenylglyoxylic acid and 3,3,5-trimethylcyclohexanol. These are detectable in the urine of rabbits and humans in less than two hours after oral administration (19,20). The ratio of mandelic acid to phenylglyoxylic acid increases with increased dosage (21). Another metabolic study in humans showed that the maximum blood levels of mandelic acid were reached in 0.5 to 1.5 hours after oral dosing (22). 

Direct determination of cyclandelate by UV spectrophotometry is not practical since the oxidative degradation product, 3,3,5-trimethylcyclohexyl phenylglyoxalate has about 55 times the absorptivity (25). Spectrophotometric determinations of cyclandelate after hydrolysis to mandelic acid and oxidation to benzaldehyde have been reported (26,27). 

Mandelic acid, a major metabolite of cyclandel-ate [3,3,5-trimethylcyclohexyl)-mandelate], is a very effective hydroxyl radical scavenger (Haenen 1989). 

The common name of the vasodilator cyclandelate is 3,5,5-trimethylcyclohexyl mandelate. Give the structure and name of the acid contained in the ester. 

However, the most representative example of an industrial establishment for this nitrilase process is the production of (R)-mandelic acid 14 and its derivatives (Scheme 28.9). Mandelic acid was discovered while heating amygda-Un, an extract of bitter almonds, with diluted hydrochloric acid. The name is derived from the German Mandel for ahnond. It is used mainly as an antibacterial. The drugs cyclandelate (vasodilator) and homatropine (used in eye drops as a cycloplegic and as a mydriatic) are esters of man-dehc acid." ... 

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