1-Octanol, also known as octan-1-ol, is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...

with the

molecular formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...

CH₃(CH₂)₇OH. It is a fatty alcohol. Many other isomers are also known generically as

octanol Octanols are alcohols with the formula C8H17OH. A simple and important member is 1-octanol, with an unbranched chain of carbons. Other commercially important octanols are 2-octanol and 2-ethylhexanol. There are 89 possible isomers In che ...

s. 1-Octanol is manufactured for the synthesis of esters for use in

perfume Perfume (, ; french: parfum) is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. Th ...

s and

flavoring A flavoring (or flavouring), also known as flavor (or flavour) or flavorant, is a food additive used to improve the taste or smell of food. It changes the perceptual impression of food as determined primarily by the chemoreceptors of the gus ...

s. It has a pungent odor.

Ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides a ...

s of octanol, such as

octyl acetate Octyl acetate, or octyl ethanoate, is an organic compound with the formula CH3(CH2)7O2CCH3. It is classified as an ester that is formed from 1-octanol (octyl alcohol) and acetic acid. It is found in oranges, grapefruits, and other citrus produc ...

, occur as components of essential oils. It is used to evaluate the lipophilicity of pharmaceutical products.

Preparation

Octanol is mainly produced industrially by the oligomerization of ethylene using

triethylaluminium Triethylaluminium is one of the simplest examples of an organoaluminium compound. Despite its name it has the formula Al2( C2H5)6 (abbreviated as Al2Et6 or TEA), as it exists as a dimer. This colorless liquid is pyrophoric. It is an industrially ...

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 Distillation, or classical distillation, is the process of separating the components or substances from a liquid mixture by using selective boiling and condensation, usually inside an apparatus known as a still. Dry distillation is the heat ...

. The Kuraray process defines an alternative route to 1-octanol, but using C4 + C4 building strategy.

1,3-Butadiene 1,3-Butadiene () is the organic compound with the formula (CH2=CH)2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two vi ...

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

Octanol and water are immiscible. The distribution of a compound between water and octanol is used to calculate the

partition coefficient In the physical sciences, a partition coefficient (''P'') or distribution coefficient (''D'') is the ratio of concentrations of a compound in a mixture of two immiscible solvents at equilibrium. This ratio is therefore a comparison of the solub ...

, ''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 The cytosol, also known as cytoplasmic matrix or groundplasm, is one of the liquids found inside cells ( intracellular fluid (ICF)). It is separated into compartments by membranes. For example, the mitochondrial matrix separates the mitochondri ...

and

lipid Lipids are a broad group of naturally-occurring molecules which includes fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids includ ...

membrane A membrane is a selective barrier; it allows some things to pass through but stops others. Such things may be molecules, ions, or other small particles. Membranes can be generally classified into synthetic membranes and biological membranes. ...

s of living systems. 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: :

\log(K_) = a + b\log(K_)

Where a and b are constants,

K_

is the stratum corneum/water partition coefficient, and

K_

is the water/octanol partition coefficient. The values of ''a'' and ''b'' vary between papers, but Cleek & Bunge have reported the values ''a'' = 0, ''b'' = 0.74.

Properties and 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. It has been examined for controlling

essential tremor Essential tremor (ET), also called benign tremor, familial tremor, and idiopathic tremor, is a medical condition characterized by involuntary rhythmic contractions and relaxations ( oscillations or twitching movements) of certain muscle groups in ...

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. 1-Octanol hydrogen bonds to

Lewis bases A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any s ...

. It is a

Lewis acid A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty Non-bonding orbital, orbital which is capable of accepting an electron pair from a Lewis Base (chemistry), base to form a Lewis a ...

in the ECW model and its acid parameters are E_A = 0.85 and C _A = 0.87.

References

{{DEFAULTSORT:Octanol, 1- Fatty alcohols Primary alcohols Alkanols

Preparation

Water/octanol partitioning

Properties and uses

See also

References