1-Octanol

Octanol
Names
IUPAC name
Octan-1-ol
Other names
1-Octanol; Capryl alcohol; Octyl alcohol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.561
Properties
C8H18O
Molar mass 130.23 g·mol−1
Density 0.824 g/cm3
Melting point −16 °C (3 °F; 257 K)
Boiling point 195 °C (383 °F; 468 K)
0.46 g/liter
Viscosity 7.36 cP (at 25 °C)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[2] It is used to evaluate the lipophilicity of pharmaceutical products.

Preparation

Octanol is 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.[2] 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 are separated by distillation.

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.[3]

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:[4]

Where a and b are constants, is the stratum corneum/ water partition coefficient, and is the water/ octanol partition coefficient. The values of a and b vary between papers, but Cleek & Bunge[5] have reported the values a=0, b=0.74.

Uses

1-Octanol is mainly consumed as a precursor to perfumes.[2] It has been examined for controlling essential tremor and other types of involuntary neurological tremors.[6]

See also

References

  1. ↑ Bhattacharjee, A.; Roy, M. N. (2010-11-17). "Density, Viscosity, and Speed of Sound of (1-Octanol + 2-Methoxyethanol),(1-Octanol + N,N-Dimethylacetamide), and (1-Octanol + Acetophenone) at Temperatures of (298.15, 308.15, and 318.15) K". Journal of Chemical & Engineering Data. 55 (12): 5914–5920. doi:10.1021/je100170v.
  2. 1 2 3 Jürgen Falbe, Helmut Bahrmann, Wolfgang Lipps, Dieter Mayer "Alcohols, Aliphatic" in Ullmann's Encyclopedia of Chemical Technology Wiley-VCH Verlag; Weinheim, 2002. doi:10.1002/14356007.a01_279
  3. ↑ Schwarzenbach, Rene P.; Gschwend, Philip M.; Imboden, Dieter M. (2003). Environmental organic chemistry. John Wiley. ISBN 0-471-35053-2.
  4. ↑ McCarley KD, Bunge AL (2001). "Pharmacokinetic Models of Dermal Absorption". Journal of Pharmaceutical Sciences. 90 (11): 1699–1719. PMID 11745728. doi:10.1002/jps.1120.
  5. ↑ Cleek RL, Bunge AL (1993). "A new method for estimating dermal absorption from chemical exposure. 1. General approach". Pharmaceutical Research. 10 (4): 497–506. PMID 8483831. doi:10.1023/A:1018981515480.
  6. ↑ Bushara K.; et al. (2004). "Pilot trial of 1-octanol in essential tremor". Neurology. 62 (1): 122–124. PMID 14718713. doi:10.1212/01.wnl.0000101722.95137.19.
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