| Description | Cyclohexanecarboxylic acid, also known as hexahydrobenzoic acid or carboxycyclohexane, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Cyclohexanecarboxylic acid is a weakly acidic compound (based on its pKa). Cyclohexanecarboxylic acid exists in all living organisms, ranging from bacteria to humans. Cyclohexanecarboxylic acid is an acidic, cheese, and fruity tasting compound. Outside of the human body,. A monocarboxylic acid that consists of cyclohexane substituted by a carboxy group.
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| 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. |
| Chemical Properties | White crystalline solid |
| Chemical Properties | Cyclohexanecarboxylic acid has a cheese-like odor. |
| Uses | Cyclohexanecarboxylic acid can be used to determine complex binding constants of the three native cyclodextrins with seven cyclohexane derivatives. |
| Uses | Paint and varnish driers, dry-cleaning soaps,
lubricating oils, stabilizer for rubber. |
| Uses | Cyclohexanecarboxylic acid may be used as an analytical standard for the determination of the analyte in wine and other alcoholic beverages, edible salts and high-salinity foods, and ethanolic extract of Centella asiatica by various analytical techniques. |
| 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 |
| Synthesis Reference(s) | The Journal of Organic Chemistry, 22, p. 1680, 1957 DOI: 10.1021/jo01363a041
Tetrahedron Letters, 21, p. 4773, 1980 DOI: 10.1016/0040-4039(80)80136-5 |
| 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. |
| 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.] |
