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Hexanol
Also known as: Hexan-1-ol, Hexyl alcohol, 111-27-3, Hexanol, N-hexanol, N-hexyl alcohol
Molecular Formula
C6H14O
Molecular Weight
102.17  g/mol
InChI Key
ZSIAUFGUXNUGDI-UHFFFAOYSA-N
FDA UNII
6CP2QER8GS

1-Hexanol is a metabolite found in or produced by Saccharomyces cerevisiae.
1 2D Structure

Hexanol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
hexan-1-ol
2.1.2 InChI
InChI=1S/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3
2.1.3 InChI Key
ZSIAUFGUXNUGDI-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCCCO
2.2 Other Identifiers
2.2.1 UNII
6CP2QER8GS
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-hexanol, Aluminum Salt

2. 1-hexyl Alcohol

3. N-hexanol

2.3.2 Depositor-Supplied Synonyms

1. Hexan-1-ol

2. Hexyl Alcohol

3. 111-27-3

4. Hexanol

5. N-hexanol

6. N-hexyl Alcohol

7. Amylcarbinol

8. 1-hydroxyhexane

9. 1-hexyl Alcohol

10. Caproyl Alcohol

11. Pentylcarbinol

12. Caproic Alcohol

13. N-hexan-1-ol

14. C6 Alcohol

15. Alcohol(c6)

16. Hexanol (van)

17. Fatty Alcohol(c6)

18. Epal 6

19. Hexyl Alcohol (natural)

20. Alcohol C-6

21. Fema No. 2567

22. Nsc 9254

23. Mfcd00002982

24. Hexanol-(1)

25. 6cp2qer8gs

26. 25917-35-5

27. Chebi:87393

28. Nsc-9254

29. Dsstox_cid_1931

30. Dsstox_rid_76410

31. Dsstox_gsid_21931

32. Caswell No. 482e

33. Hydroxyhexane

34. Hexanols

35. Fema Number 2567

36. Cas-111-27-3

37. He2

38. Hsdb 565

39. Einecs 203-852-3

40. Unii-6cp2qer8gs

41. Epa Pesticide Chemical Code 079047

42. Brn 0969167

43. Caproalcohol

44. Hexalcohol

45. Hexyl Alcohol, Active

46. N-hexylalcohol

47. Ai3-08157

48. N-hexenol

49. Nat.hexanol

50. Exxal 6

51. Einecs 247-346-0

52. Hexanol-cmpd

53. Exxal 6 (salt/mix)

54. Bdbm9

55. 1-hexanol, 98%

56. Hexyl Alcohol, Fcc, Fg

57. 1-hexanol [hsdb]

58. 1-hexanol [mi]

59. Ec 203-852-3

60. N-c6h13oh

61. Schembl1877

62. Hexyl Alcohol [fcc]

63. Natural Hexyl Alcohol

64. C6h13oh

65. Hexyl Alcohol [fhfi]

66. Hexyl Alcohol [inci]

67. Wln: Q6

68. 4-01-00-01694 (beilstein Handbook Reference)

69. Mls001055374

70. Un 2282 (salt/mix)

71. Bidd:er0298

72. Chembl14085

73. 1-hexanol, Analytical Standard

74. Dtxsid8021931

75. 1-hexanol, Anhydrous, >=99%

76. Nsc9254

77. 1-hexanol, Reagent Grade, 98%

78. Dtxsid001022586

79. Hms3039l08

80. Bcp29486

81. Zinc1699882

82. Tox21_201335

83. Tox21_302953

84. Lmfa05000117

85. Stl282713

86. Un2282

87. Akos009031422

88. 1-hexanol 100 Microg/ml In Methanol

89. Hy-w032022

90. Alcohol C-6, Natural, Natural Hexanol

91. 1-hexanol, Purum, >=98.0% (gc)

92. 1-hexyl Alcohol Pound>>1-hexylalcohol

93. Ncgc00090949-01

94. Ncgc00090949-02

95. Ncgc00256385-01

96. Ncgc00258887-01

97. Hexanols [un2282] [flammable Liquid]

98. Ls-13216

99. Smr000677945

100. 1-hexanol, Saj Special Grade, >=99.0%

101. 1-hexanol, Vetec(tm) Reagent Grade, 98%

102. Cs-0076046

103. Ft-0607887

104. H0130

105. Hexyl Alcohol, Natural, >=98%, Fcc, Fg

106. En300-19338

107. Q76933

108. 1-hexanol, Reagentplus(r), >=99.5% (gc)

109. J-002549

110. F0001-0237

111. Z955123546

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 102.17 g/mol
Molecular Formula C6H14O
XLogP32
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count4
Exact Mass102.104465066 g/mol
Monoisotopic Mass102.104465066 g/mol
Topological Polar Surface Area20.2 Ų
Heavy Atom Count7
Formal Charge0
Complexity27.4
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Mesh Heading: Anesthetics, Nicotinic antagonists

National Library of Medicine, SIS; ChemIDplus Record for 1-hexanol (111-27-3). Available from, as of April 13, 2006: https://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anesthetics

Agents capable of inducing a total or partial loss of sensation, especially tactile sensation and pain. They may act to induce general ANESTHESIA, in which an unconscious state is achieved, or may act locally to induce numbness or lack of sensation at a targeted site. (See all compounds classified as Anesthetics.)


Nicotinic Antagonists

Drugs that bind to nicotinic cholinergic receptors (RECEPTORS, NICOTINIC) and block the actions of acetylcholine or cholinergic agonists. Nicotinic antagonists block synaptic transmission at autonomic ganglia, the skeletal neuromuscular junction, and at central nervous system nicotinic synapses. (See all compounds classified as Nicotinic Antagonists.)


5.2 Absorption, Distribution and Excretion

The permeability of excised rat skin to 1-hexanol was increased by hydration for the first ten hours, then returned to baseline.

Snyder, R. (ed.). Ethel Browning's Toxicity and Metabolism of Industrial Solvents. Second Edition. Volume 3 Alcohols and Esters. New York, NY: Elsevier, 1992., p. 179


The in vitro dermal flux in human skin (epidermis) was reported to be 0.044 mg/sq cm/hr, indicating a low rate of dermal uptake.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 6:441


5.3 Metabolism/Metabolites

Through successive oxidation processes, 1-hexanol is converted to hexanoic acid, which then undergoes beta-oxidation.

Snyder, R. (ed.). Ethel Browning's Toxicity and Metabolism of Industrial Solvents. Second Edition. Volume 3 Alcohols and Esters. New York, NY: Elsevier, 1992., p. 179


1-Hexanol has a high affinity for ADH /alcohol dehydrogenase/, similar to amyl and n-octyl alcohol, and is a potent inhibitor of ethanol oxidation. 1-Hexanol is metabolized by direct conjugation with glucuronic acid and by oxidation to the carboxylic acid and eventually to carbon dioxide.

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. 4610


Metabolic studies in rabbits indicate that oxidation to hexanoic acid is the major pathway, mediated by alcohol dehydrogenase and aldehyde dehydrogenase. Direct conjugation with glucuronic acid is a minor pathway.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 6:440


5.4 Mechanism of Action

... Ethanol and 1-hexanol were found to have two competing concentration-dependent effects on the Ca(2+)- and phorbol ester- or diacylglycerol-dependent activities of PKCalpha associated with either RhoA or Cdc42, consisting of a potentiation at low alcohol levels and an attenuation of activity at higher levels. Measurements of the Ca(2+), phorbol ester, and diacylglycerol concentration-response curves for Cdc42-induced activation indicated that the activating effect corresponded to a shift in the midpoints of each of the curves to lower activator concentrations, while the attenuating effect corresponded to a decrease in the level of activity induced by maximal activator levels. The presence of ethanol enhanced the interaction of PKCalpha with Cdc42 within a concentration range corresponding to the potentiating effect, whereas the level of binding was unaffected by higher ethanol levels that were found to attenuate activity.

PMID:14556642 Slater SJ et al; Biochemistry 42(41):12105-14 (2003)


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