1-Octanol

Preparation

Octanol is mainly produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products. This route is known as the Ziegler alcohol synthesis. An idealized synthesis is shown: :Al(C2H5)3 + 9 C2H4 → Al(C8H17)3 :Al(C8H17)3 + 3 O + 3 H2O → 3 HOC8H17 + Al(OH)3 The process generates a range of alcohols, which can be separated by distillation.

The Kuraray process defines an alternative route to 1-octanol, but using C4 + C4 building strategy. 1,3-Butadiene is dimerized concomitant with the addition of one molecule of water. This conversion is catalyzed by palladium complexes. The resulting doubly unsaturated alcohol is then hydrogenated.

Water/octanol partitioning

Main article: Octanol-water partition coefficient

Octanol and water are immiscible. The distribution of a compound between water and octanol is used to calculate the partition coefficient, P, of that molecule (often expressed as its logarithm to the base 10, log P). Water/octanol partitioning is a relatively good approximation of the partitioning between the cytosol and lipid membranes of living systems.{{Cite book

Many dermal absorption models consider the stratum corneum/ water partition coefficient to be well approximated by a function of the water/octanol partition coefficient of the form:{{cite journal

:\log(K_{sc/w}) = a + b\log(K_{w/o})

Where a and b are constants, K_{sc/w} is the stratum corneum/water partition coefficient, and K_{w/o} is the water/octanol partition coefficient. The values of a and b vary between papers, but Cleek & Bunge{{cite journal

Properties and uses

With a flash point of 81 °C, 1-octanol is not seriously flammable, though its autoignition temperature is as low as 245 °C. 1-Octanol is mainly consumed as a precursor to perfumes.

Octanol has a sedative and anesthetic effect in animal studies, though 1-octanol may not be the most potent isomer. 1-Octanol has been examined for controlling essential tremor and other types of involuntary neurological tremors because evidence indicates it can relieve tremor symptoms at lower doses than are required to obtain a similar level of symptomatic relief from consumption of ethanol, thereby reducing the risk of alcohol intoxication at therapeutic dosages.

References

References

1. {{GESTIS
2. (2010-11-17). "Density, Viscosity, and Speed of Sound of (1-Octanol + 2-Methoxyethanol),(1-Octanol + N,N-Dimethylacetamide), and (1-Octanol + Acetophenone) at Temperatures of (298.15, 308.15, and 318.15) K". Journal of Chemical & Engineering Data.
3. "Эфирные масла цитрусовых и их химический состав".
4. (2013). "Alcohols, Aliphatic". American Cancer Society.
5. J. Grub. (2012). "Butadiene".
6. (September 1981). "A relationship between alcohol intoxication and the disordering of brain membranes by a series of short-chain alcohols". The Journal of Pharmacology and Experimental Therapeutics.
7. (October 1992). "Lipid solubility of sedative-hypnotic drugs influences hypothermic and hypnotic responses of long-sleep and short-sleep mice". The Journal of Pharmacology and Experimental Therapeutics.
8. (December 1993). "Alcohol modulation of cloned GABAA receptor-channel complex expressed in human kidney cell lines". Brain Research.
9. (January 1998). "Pharmacological properties of T-type Ca2+ current in adult rat sensory neurons: effects of anticonvulsant and anesthetic agents". Journal of Neurophysiology.
10. (August 2004). "Channel gating of the glycine receptor changes accessibility to residues implicated in receptor potentiation by alcohols and anesthetics". The Journal of Biological Chemistry.
11. (March 2010). "Numerous classes of general anesthetics inhibit etomidate binding to gamma-aminobutyric acid type A (GABAA) receptors". The Journal of Biological Chemistry.
12. (January 2004). "Pilot trial of 1-octanol in essential tremor". Neurology.
13. (October 2011). "An open-label, single-dose, crossover study of the pharmacokinetics and metabolism of two oral formulations of 1-octanol in patients with essential tremor". Neurotherapeutics.