1-Octanol, also known as octan-1-ol, is the organic compound with the molecular formula CH3(CH2)7OH. It is a fatty alcohol. Many other isomers are also known generically as octanols. 1-Octanol is manufactured for the synthesis of esters for use in perfumes and flavorings. It has a pungent odor. Esters of octanol, such as octyl acetate, occur as components of essential oils.[3] It is used to evaluate the lipophilicity of pharmaceutical products.
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| Names | |
|---|---|
| Preferred IUPAC name Octan-1-ol | |
| Other names 1-Octanol; n-Octanol; Capryl alcohol; Octyl alcohol | |
| Identifiers | |
3D model (JSmol) | |
| 1697461 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.003.561 |
| EC Number |
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| 82528 | |
| KEGG | |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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| Properties | |
| C8H18O | |
| Molar mass | 130.231 g·mol−1 |
| Appearance | Colorless liquid[1] |
| Odor | Aromatic[1] |
| Density | 0.83 g/cm3 (20 °C)[1] |
| Melting point | −16 °C (3 °F; 257 K)[1] |
| Boiling point | 195 °C (383 °F; 468 K)[1] |
| 0.3 g/L (20 °C)[1] | |
| Viscosity | 7.36 cP[2] |
| Hazards | |
| GHS labelling: | |
 | |
| Warning | |
| H319 | |
| P264, P280, P305+P351+P338, P337+P313 | |
| NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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.[3] 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.[4]
Water/octanol partitioning
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.[5]
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:[6]
Where a and b are constants, 
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.[3] It 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 alcohol intoxication at therapeutic dosages.[8]
1-Octanol hydrogen bonds to Lewis bases. It is a Lewis acid in the ECW model and its acid parameters are EA = 0.85 and C A = 0.87.[9]