Contents

1-Octanol

Octanol

Names
Preferred IUPAC name Octan-1-ol
Other names 1-Octanol; n-Octanol; Capryl alcohol; Octyl alcohol
Identifiers
CAS Number	111-87-5 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1697461
ChEBI	CHEBI:16188
ChEMBL	ChEMBL26215 Y
ChemSpider	932 Y
ECHA InfoCard	100.003.561
EC Number	203-917-6
Gmelin Reference	82528
IUPHAR/BPS	4278
KEGG	C00756
PubChem CID	957
UNII	NV1779205D Y
CompTox Dashboard (EPA)	DTXSID7021940
InChI InChI=1S/C8H18O/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3 N Key: KBPLFHHGFOOTCA-UHFFFAOYSA-N N InChI=1/C8H18O/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3 Key: KBPLFHHGFOOTCA-UHFFFAOYAH
SMILES CCCCCCCCO
Properties
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]
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319
Precautionary statements	P264, P280, P305+P351+P338, P337+P313
NFPA 704 (fire diamond)	1 2 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Chemical compound

1-Octanol, also known as octan-1-ol, is the organic compound with the molecular formulaCH₃(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[edit]

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[edit]

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.

Properties and uses[edit]

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 bondstoLewis bases. It is a Lewis acid in the ECW model and its acid parameters are E_A = 0.85 and C _A = 0.87.^[9]

See also[edit]

• 2-Octanol

References[edit]