Cyclohexanecarboxylic acid

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Cyclohexanecarboxylic acid
Cyclohexanecarboxylic acid.svg
Names
Preferred IUPAC name
Cyclohexanecarboxylic acid [1]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.465 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C7H12O2/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2,(H,8,9)
    Key: NZNMSOFKMUBTKW-UHFFFAOYSA-N
  • InChI=1/C7H12O2/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2,(H,8,9)
    Key: NZNMSOFKMUBTKW-UHFFFAOYAH
  • O=C(O)C1CCCCC1
Properties
C7H12O2
Molar mass 128.171 g·mol−1
Appearancewhite solid
Density 1.0274 g/cm3
Melting point 30–31 °C (86–88 °F; 303–304 K)
Boiling point 232–234 °C (450–453 °F; 505–507 K)
−83.24·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cyclohexanecarboxylic acid is the organic compound with the formula C6H11CO2H. It is the carboxylic acid of cyclohexane. It is a colorless oil that crystallizes near room temperature. [2]

Contents

Preparation and reactions

It is prepared by hydrogenation of benzoic acid.

Cyclohexanecarboxylic acid is a precursor to the nylon-6 precursor caprolactam via its reaction with nitrosylsulfuric acid. It can also be oxidized to cyclohexene. [2]

Cyclohexanecarboxylic acid exhibits the reactions typical of carboxylic acids, including its conversion to the acid chloride cyclohexanecarbonyl chloride using thionyl chloride [3] or oxalyl chloride [4] and to various other acyl derivatives either directly or by way of the acyl halide.

Biochemistry

Cyclohexanecarboxylic acid is a product in the metabolism of benzoic acid in certain microorganisms. [5] In rat models, cyclohexanecarboxylic acid was found to have anti-convulsant acitvity in a manner similar to valproic acid. [6]

Derivatives related to cyclohexanecarboxylic acid include:

References

  1. ↑ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 303, 639. doi:10.1039/9781849733069-00648. ISBN   978-0-85404-182-4.
  2. 1 2 Maki, Takao; Takeda, Kazuo. "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_555. ISBN   978-3-527-30673-2..
  3. ↑ Cope, Arthur C.; Ciganek, Engelbert (1959). "N,N-Dimethylcyclohexylmethylamine". Organic Syntheses. 39: 19. doi:10.15227/orgsyn.039.0019.
  4. ↑ Spessard, Gary O.; Chan, Wan Kit; Masamune, S. (1983). "Preparation of thiol esters: S-tert-butyl cyclohexanecarbothioate and S-tert-butyl 3α,7α,12α-trihydroxy-5β-cholane-24-thioate". Organic Syntheses. 61: 134. doi:10.15227/orgsyn.061.0134.
  5. ↑ Elshahed, M. S.; Bhupathiraju, V. K.; Wofford, N. Q.; Nanny, M. A.; McInerney, M. J. (2001). "Metabolism of benzoate, cyclohex-1-ene carboxylate, and cyclohexane carboxylate by "Syntrophus aciditrophicus" strain SB in syntrophic association with H2-using microorganisms". Applied and Environmental Microbiology. 67 (4): 1728–1738. doi:10.1128/AEM.67.4.1728-1738.2001. PMC   92791 . PMID   11282627.
  6. ↑ Liu, M. J.; Pollack, G. M. (1994). "Pharmacokinetics and pharmacodynamics of valproate analogues in rats. IV. Anticonvulsant action and neurotoxicity of octanoic acid, cyclohexanecarboxylic acid, and 1-methyl-1-cyclohexanecarboxylic acid". Epilepsia. 35 (1): 234–243. doi:10.1111/j.1528-1157.1994.tb02939.x. PMID   8112253.
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