 | |
 | |
| 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 |
|
| 82528 | |
| KEGG | |
| UNII | |
| |
| |
| 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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
1-Octanol, also known as octan-1-ol, is theorganic compound with themolecular formula CH3(CH2)7OH. It is afatty alcohol. Many otherisomers are also known generically asoctanols. 1-Octanol is manufactured for the synthesis of esters for use inperfumes andflavorings. It has a pungent odor.Esters of octanol, such asoctyl acetate, occur as components ofessential oils[3] (grapefruit oil, orange oil, bergamot oil, mandarin oil and lime oil[4]). It is used to evaluate the lipophilicity of pharmaceutical products.
Octanol is mainly produced industrially by the oligomerization ofethylene usingtriethylaluminium followed by oxidation of thealkylaluminium products. This route is known as theZiegler alcohol synthesis.[3] An idealized synthesis is shown:
The process generates a range of alcohols, which can be separated bydistillation.
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.[5]
Octanol and water areimmiscible. The distribution of a compound between water and octanol is used to calculate thepartition coefficient,P, of that molecule (often expressed as its logarithm to the base 10, logP). Water/octanol partitioning is a relatively good approximation of the partitioning between thecytosol andlipidmembranes of living systems.[6]
Many dermal absorption models consider thestratum corneum/ water partition coefficient to be well approximated by a function of the water/octanol partition coefficient of the form:[7]
Where a and b are constants, is the stratum corneum/water partition coefficient, and is the water/octanol partition coefficient. The values ofa andb vary between papers, but Cleek & Bunge[8] have reported the valuesa = 0,b = 0.74.
With a flash point of 81 °C, 1-octanol is not seriously flammable, though itsautoignition temperature is as low as 245 °C. 1-Octanol is mainly consumed as a precursor to perfumes.[3] 1-Octanolhydrogen bonds toLewis bases. It is aLewis acid in theECW model and its acid parameters are EA = 0.85 and CA = 0.87.[9]
Octanol has asedative andanesthetic effect in animal studies, though 1-octanol may not be the most potent isomer.[10][11][12][13][14][15] 1-Octanol has been examined for controllingessential 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.[16][17]
