Chemical Properties
Cyclohexanecarboxylic acid has a cheese-like odor.
Chemical Properties
White crystalline solid
Definition
ChEBI: A monocarboxylic acid that consists of cyclohexane substituted by a carboxy group.
Taste threshold values
Taste characteristics at 5 ppm: fruity, woody, berry-like with green dirty nuances
General Description
Cyclohexanecarboxylic acid, the saturated analog of benzoic acid, is categorized under the family of volatile organic compounds (VOCs). It is typically used as a flavoring ingredient.
Biochem/physiol Actions
Cyclohexanecarboxylic acid undergoes microbial degradation by a strain of Antherobacter to form para-hydroxybenzoic acid. Cyclohexanecarboxylic acid undergoes aromatization and converts to Hippuric acid in rat liver extracts in vitro. Cyclohexanecarboxylic acid is the starting reagent for the synthesis of polyketide-type antibiotics, Phoslactomycins.
Metabolism
Cyclohexanecarboxylic acid is converted to 1-cyclohexanecarbonyl-β-d-glucose and N-cyclohexanecarbonyl-l-aspartic acid when administered to leaf disks of Phaseolus vulgaris in the light[1].
Purification Methods
Crystallise the acid from hot H2O (solubility is 0.2% w/w at 15o), it is soluble in organic solvents. Also distil it at as high a vacuum as possible and warm the condenser as it solidifies on cooling.The acid chloride M 146.6, has b 184o/atm, d2 5 1.096, the methyl ester has b 183o/atm, and the S-benzylisothiuronium salt
has m 165-166o (from EtOH). [Beilstein 9 H 7, 9 I 5, 9 II 6, 9 III15, 9 IV 16.]
References
[1] J.G. Severson Jr., C. E. S., B. A. Bohm. (1970). The metabolism of cyclohexanecarboxylic acid in phaseolus vulgaris. Phytochemistry, 9 1, Pages 107-110. https://doi.org/
10.1016/S0031-9422(00)86620-0
