Cyclohexaneacetic Acid Research Articles

Metabolism of n-Alkylcyclohexanes with an even number of carbon atoms in the side chain by Micrococcus sp. RCO-4M

The metabolism of n-alkyleyclohexanes with an even number of carbon atoms (6, 8, 10, 12, 14) in the side chain by Micrococcus sp. RCO-4M was investigated. Evidence for the formation of cyclohexanecarboxylic acid (I), cyclohexaneacetic acid (II), 1-cyclohexenecarboxylic acid (III), 6-hydroxyhexanoic acid (IV), adipic acid (V), and trans-4-hydroxycyclohexaneacetic acid (VI) is presented. The presence of products (II), (IV) and (V) especially represent the complete degradation of n-alkylcyclohexanes with an even number of carbon atoms in the side chain by a single organism. The occurrence of a newly-identified product (VI) suggests that a new metabolic pathway for n-alkylcyclohexanes with even-carbon-number side chain operates in this organism.

Hydrogen bonded solvation structures in the reaction of car☐ylic acids and anilines in cyclohexane acetic acid solutions

Short range solvation effects have been studied in reactions of car☐ylic acids and primary, secondary and tertiary amine anilines in cyclohexane and cyclohexane-acetic acid mixed solvents. Acetic acid is found to hydrogen bond with the amine protons of primary and secondary anilines. Trichloroacetic acid reacts as a trimeric structure. Acetic acid interferes with reactions of trichloroacetic acid, possibly by forming a tight heterodimer.

Synthesis of [14C]‐labelled AY‐30,068

Abstract[14C]AY‐30,068 (cis‐1,8‐diethyl‐2,3,4,9‐tetrahydro‐4‐(2‐propenyl)‐1H‐carbazole‐1‐acetic acid), a potent analgesic agent, was prepared by incorporating [14C]methyl iodide via a Wittig reaction. The intermediate aldehyde was synthesized in six steps from cis‐1‐ethyl‐2‐oxo‐4‐(2‐propenyl)cyclohexaneacetic acid methyl ester. Three batches of the [14C]labelled AY‐30,068 were produced, giving a combined overall yield of 9% from [14C]methyl iodide (sp. act. 51.2, 17.7 and 4.4 μCi/mg; 97.5, 98.3, and 98.6% radiochemcical purity, respectively).

Metabolism of cyclohexaneacetic acid and cyclohexanebutyric acid by Arthrobacter sp. strain CA1.

A strain of Arthrobacter was isolated by enrichment culture with cyclohexaneacetate as the sole source of carbon and grew with a doubling time of 4.2 h. In addition to growing with cyclohexaneacetate, the organism also grew with cyclohexanebutyrate at concentrations not above 0.05%, and with a variety of alicyclic ketones and alcohols. Oxidation of cyclohexaneacetate proceeded through formation of the coenzyme A (CoA) ester followed by initiation of a beta-oxidation cycle. beta-Oxidation was blocked before the second dehydrogenation step due to the formation of a tertiary alcohol, and the side chain was eliminated as acetyl-CoA by the action of (1-hydroxycyclohexan-1-yl)acetyl-CoA lyase. The cyclohexanone thus formed was degraded by a well-described route that involves ring-oxygen insertion by a biological Baeyer-Villiger oxygenase. All enzymes of the proposed metabolic sequence were demonstrated in cell-free extracts. Arthrobacter sp. strain CA1 synthesized constitutive beta-oxidative enzymes, but further induction of enzymes active toward cyclohexaneacetate and its metabolites could occur during growth with the alicyclic acid. Other enzymes of the sequence, (1-hydroxycyclohexan-1-yl)acetyl-CoA lyase and enzymes of cyclohexanone oxidation, were present at negligible levels in succinate-grown cells but induced by growth with cyclohexaneacetate. The oxidation of cyclohexanebutyrate was integrated into the pathway for cyclohexaneacetate oxidation by a single beta-oxidation cycle. Oxidation of the compound could be divided into two phases. Initial oxidation to (1-hydroxycyclohexan-1-yl)acetate could be catalyzed by constitutive enzymes, whereas the further degradation of (1-hydroxycyclohexan-1-yl)acetate was dependent on induced enzyme synthesis which could be inhibited by chloramphenicol with the consequent accumulation of cyclohexaneacetate and (1-hydroxycyclohexan-1-yl)acetate.

The Degradation of n-Alkylcycloalkanes by a Mixed Bacterial Culture

Mycobacterium rhodochrous strain 7EIC grows with dodecylcyclohexane at the expense of acetyl fragments released by β-oxidation of the side-chain. Cyclohexaneacetic acid, which is not amenable to β-oxidation and is not oxidized by this organism, accumulates in significant yield. In combination with Arthrobacter strain CA1, which degrades cyclohexaneacetic acid by a novel pathway, a stable mixed culture is established that is capable of the complete degradation of dodecylcyclohexane and related hydrocarbons.

Viscosities of binary solutions of non-electrolytes

Viscosities and molar volumes of binary solutions,viz., Toluene-Nitrobenzene, Toluene-Bromobenzene, Toluene-Cyclohexanone, Cyclohexane-Cyclohexanone, Cyclohexane-Nitrobenzene, Cyclohexane-Acetic acid, Cyclohexane-Propionic acid and Cyclohexane-Butyric acid have been measured. The experimental results have been discussed in terms of viscosity-composition relations developed for binary solutions by Grunberg and Nissan and Katti and Chaudhri.

Studies in the relationship between molecular structure and chromatographic behaviour : IX. An assessment of the role of polyamide surface in the thin-layer chromatography of phenols

The chromatographic behaviour of some 2-substituted alkylphenols on cellulose impregnated with polyamide (10%) as the stationary phase with (a) cyclohexane—acetic acid (93:7, v/v) and (b) aqueous acetic acid (10%, v/v) as the mobile phase has been studied. The results obtained are compared with those obtained from adsorption chromatography, and reversed-phase thin-layer chromatography. The mechanism of the chromatographic process is explained in terms of the breaking of the phenolic/polyamide hydrogen bonds as a result of (i) solvation of the hydrophobic part of the molecule with the non-aqueous solvent (a), or (ii) solvation of the phenolic group with the aqueous solvent (b). The hypothesis of the duality of behaviour of polyamide is discounted.

Synthesis and stereochemistry in B/C ring juncture of lactam-carbinol A, a degradation product of securinine.

Cis-and trans-2-Hydroxy-2-(2-pyridyl) cyclohexaneacetic acid, (X) and (VIII), were synthesized and their stereochemistries discussed. The latter (VIII) was converted into racemic lactam-carbinol A (I), which showed the same infrared spectrum in chloroform as that of natural lactam-carbinol A obtained by degradation of securinine. The present work proved unequivocally the stereochemistries in B/C ring junctures of lactamcarbinols A (I) and B (II), and quinolizidines A (IV) and B (V), degradation products of securinine.