1-Octanol

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Octanol
Skeletal formula
Space-filling model
Names
IUPAC name
Octan-1-ol
Other names
1-Octanol; Capryl alcohol; Octyl alcohol
Identifiers
111-87-5 YesY
ChEMBL ChEMBL26215 N
ChemSpider 932 N
4278
Jmol-3D images Image
PubChem 957
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)
4.60 g/liter[1]
Viscosity 7.36 cP (at 25 °C)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

1-Octanol 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. 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 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 are separated by distillation.

Water/octanol partitioning[edit]

Main article: Partition coefficient

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.[4]

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:[5]

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

Where a and b are constants,K_{sc/w} is the stratum corneum/ water partition coefficient, andK_{w/o} is the water/ octanol partition coefficient. The values of a and b vary between papers, but Cleek & Bunge[6] have reported the values a=0, b=0.74.

Uses[edit]

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.[7]

See also[edit]

References[edit]

  1. ^ Lide, D. R., ed. (2013-2014). CRC Handbook of Chemistry and Physics (94th ed.). Boca Raton (FL): CRC Press.
  2. ^ 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. 
  3. ^ a b c 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
  4. ^ Schwarzenbach, Rene P.; Gschwend, Philip M.; Imboden, Dieter M. (2003). Environmental organic chemistry. John Wiley. ISBN 0-471-35053-2. 
  5. ^ McCarley KD, Bunge AL (2001). "Pharmacokinetic Models of Dermal Absorption". Journal of Pharmaceutical Sciences 90 (11): 1699–1719. doi:10.1002/jps.1120. PMID 11745728. 
  6. ^ Cleek RL, Bunge AL (1993). "A new method for estimating dermal absorption from chemical exposure. 1. General approach". Pharmaceutical Research 10 (4): 497–506. doi:10.1023/A:1018981515480. PMID 8483831. 
  7. ^ Bushara K. et al. (2004). "Pilot trial of 1-octanol in essential tremor". Neurology 62 (1): 122–124. doi:10.1212/01.wnl.0000101722.95137.19. PMID 14718713.