98-89-5

Synthesis Reference(s)

The Journal of Organic Chemistry, 22, p. 1680, 1957 DOI: 10.1021/jo01363a041Tetrahedron Letters, 21, p. 4773, 1980 DOI: 10.1016/0040-4039(80)80136-5

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.

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.]

Application

Cyclohexanecarboxylic acid is a precursor to the nylon-6 precursor caprolactam via its reaction with nitrosylsulfuric acid. It can also be oxidized to cyclohexene. Cyclohexanecarboxylic acid exhibits the reactions typical of carboxylic acids, including its conversion to the acid chloride cyclohexanecarbonyl chloride.

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.