# 1-Octanol

Names Identifiers Preferred IUPAC name Octan-1-ol Other names 1-Octanol; n-Octanol; Capryl alcohol; Octyl alcohol CAS Number 111-87-5 3D model (JSmol) Interactive image Beilstein Reference 1697461 ChEBI CHEBI:16188 ChEMBL ChEMBL26215 ChemSpider 932 ECHA InfoCard 100.003.561 EC Number 203-917-6 Gmelin Reference 82528 IUPHAR/BPS 4278 KEGG C00756 PubChem CID 957 UNII NV1779205D CompTox Dashboard (EPA) InChI InChI=1S/C8H18O/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3 Key: KBPLFHHGFOOTCA-UHFFFAOYSA-N InChI=1/C8H18O/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3Key: KBPLFHHGFOOTCA-UHFFFAOYAH SMILES CCCCCCCCO Chemical formula 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] Solubility in water 0.3 g/L (20 °C)[1] Viscosity 7.36 cP[2] GHS pictograms GHS Signal word Warning GHS hazard statements H319 GHS precautionary statements P264, P280, P305+351+338, P337+313 NFPA 704 (fire diamond) Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is  ?) Infobox references

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.

## 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]

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

Where a and b are constants, ${\displaystyle K_{sc/w}}$ is the stratum corneum/water partition coefficient, and ${\displaystyle K_{w/o}}$ is the water/octanol partition coefficient. The values of a and b vary between papers, but Cleek & Bunge[7] have reported the values a = 0, b = 0.74.

## Uses[]

With a flash point of 81 °C, 1-octanol is not seriously flammable, though its autoignition point 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.