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Chemistry

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Also known as: 108-93-0, Cyclohexyl alcohol, Hexahydrophenol, 1-cyclohexanol, Hydrophenol, Hydroxycyclohexane

Molecular Formula

C₆H₁₂O

Molecular Weight

100.16 g/mol

InChI Key

HPXRVTGHNJAIIH-UHFFFAOYSA-N

FDA UNII

8E7S519M3P

Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.

1 2D Structure

Cyclohexanol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

cyclohexanol

2.1.2 InChI

InChI=1S/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2

2.1.3 InChI Key

HPXRVTGHNJAIIH-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CCC(CC1)O

2.2 Other Identifiers

2.2.1 UNII

8E7S519M3P

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cyclohexanols

2.3.2 Depositor-Supplied Synonyms

1. 108-93-0

2. Cyclohexyl Alcohol

3. Hexahydrophenol

4. 1-cyclohexanol

5. Hydrophenol

6. Hydroxycyclohexane

7. Hexalin

8. Hydralin

9. Adronal

10. Naxol

11. Adronol

12. Anol

13. Cykloheksanol

14. Cicloesanolo

15. Phenol, Hexahydro-

16. Cicloesanolo [italian]

17. Cykloheksanol [polish]

18. Cyclohexanone Cyclohexanol Mixture

19. Cyclohexan-1-ol

20. Nsc 403656

21. Mfcd00003855

22. Chebi:18099

23. 8e7s519m3p

24. Nsc-403656

25. Cxl

26. Cyclohexanols

27. Dsstox_cid_1894

28. Dsstox_rid_76390

29. Dsstox_gsid_21894

30. Hydroxycyclohexane; Nsc 403656; Nsc 54711; Naxol; Phenol, Hexahydro-

31. Cas-108-93-0

32. Hsdb 61

33. Ccris 5896

34. Einecs 203-630-6

35. Brn 0906744

36. Cylcohexanol

37. Unii-8e7s519m3p

38. Ai3-00040

39. Cyclohexyl-alcohol

40. Cyclohexane, Hydroxy-

41. Bdbm5

42. Cyanomethylthioacetic Acid

43. Cyclohexanol [mi]

44. Bmse000431

45. Wln: L6tj Aq

46. Cyclohexanol [hsdb]

47. Ec 203-630-6

48. Schembl5545

49. 4-06-00-00020 (beilstein Handbook Reference)

50. Mls001055343

51. Bidd:er0291

52. Chembl32010

53. Cyclohexanol, P.a., 99.0%

54. Dtxsid4021894

55. Cyclohexanol, Analytical Standard

56. Hms3039k08

57. Zinc1532765

58. Tox21_201481

59. Tox21_302803

60. Bbl013186

61. Cyclohexanol, Reagentplus(r), 99%

62. Nsc403656

63. Stl163965

64. Akos000119038

65. Zinc100502981

66. Db03703

67. Rp10050

68. Ncgc00090982-01

69. Ncgc00090982-02

70. Ncgc00256434-01

71. Ncgc00259032-01

72. Smr000677941

73. Cyclohexanol, Puriss., >=99.0% (gc)

74. Cyclohexanol, Saj First Grade, >=95.0%

75. Db-040851

76. Cs-0017198

77. Cyclohexanol, Jis Special Grade, >=98.0%

78. Ft-0624192

79. Ft-0641073

80. Cyclohexanol, Vetec(tm) Reagent Grade, 98%

81. C00854

82. Q423282

83. Q-200903

84. F0001-0184

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₆H₁₂O
Molecular Weight	100.16 g/mol
XLogP3	1.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	0
Exact Mass	100.088815002 g/mol
Monoisotopic Mass	100.088815002 g/mol
Topological Polar Surface Area	20.2 Å²
Heavy Atom Count	7
Formal Charge	0
Complexity	46.1
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 Absorption, Distribution and Excretion

The substance can be absorbed into the body by inhalation and by ingestion.

International Program on Chemical Safety/Commission of the European Communities; International Chemical Safety Card on Cyclohexanol (November 1998). Available from, as of May 20, 2010: https://www.inchem.org/pages/icsc.html

Animal expt ... In large doses ... /cyclohexanol/ is readily absorbed from the skin ... .

Browning, E. Toxicity and Metabolism of Industrial Solvents. New York: American Elsevier, 1965., p. 386

Following oral admin ... to rabbits, cmpd is excreted in urine in conjugation with sulfuric & glucuronic acids. Similar results were obtained when animals were subjected to repeated inhalation of cmpd.

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 4648

... Rabbits exposed to lowest concn ... 145 ppm cyclohexanol in air, showed no incr in conjugation of urinary sulfates but excreted 5 times normal amt glucuronic acid.

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 4648

... Incr in glucuronic acid in urine was paralleled by a decr in percentage of inorg sulfates. ... That the urinary sulfate ratio became normal when exposure ceased ... led ... to ... /conclusion/ that there was no prolonged retention in organism.

Browning, E. Toxicity and Metabolism of Industrial Solvents. New York: American Elsevier, 1965., p. 386

4.2 Metabolism/Metabolites

Cyclohexane was hydroxylated to cyclohexanol by rat liver microsomes in presence of NADPH & oxygen. Pretreatment with phenobarbital at 80 mg/kg/day ip stimulated activity 6-fold, while benzopyrene pretreatment at 20 mg/kg ip lowered cyclohexane hydroxylation.

PMID:4388853 ULLRICH V; HOPPE-SEYLER'S Z PHYSIOL CHEM 350 (3): 357 (1969)

Cyclohexanol was identified as the urinary metabolite after admin of cyclohexylamine hydrochloride to rats, rabbits, & guinea pigs (50-500 mg/kg, orally or ip) and humans (25 or 200 mg, orally).

PMID:4655821 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1174231 RENWICK AG, RT WILLIAMS; BIOCHEM J 129 (4): 857 (1972)

Fed to rabbits, /cyclohexanol/ ... Is mostly excreted as the glucuronide conjugate (60% of the dose), but a small amt is oxidized further into trans-cyclohexane-1,2-diol (6%).

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 222

Hepatic NAD-dependent alcohol dehydrogenase ... is responsible for metabolism of ... cyclohexanol ...

Testa, B. and P. Jenner. Drug Metabolism: Chemical & Biochemical Aspects. New York: Marcel Dekker, Inc., 1976., p. 310

For more Metabolism/Metabolites (Complete) data for Cyclohexanol (8 total), please visit the HSDB record page.

4.3 Biological Half-Life

No reports found; [TDR, p. 430]

TDR - Ryan RP, Terry CE, Leffingwell SS (eds). Toxicology Desk Reference: The Toxic Exposure and Medical Monitoring Index, 5th Ed. Washington DC: Taylor & Francis, 1999., p. 430

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