Octanol
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2008-07-01T13:38:20Z
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{{Chembox new
| Name = '''Octanol'''
| ImageFile = 1-Octanol.png
| ImageSize = 200px
| ImageName = 1-Octanol
| IUPACName = 1-octanol
| OtherNames = capryl alcohol<br />octyl alcohol
| Section1 = {{Chembox Identifiers
| CASNo = 111-87-5
| SMILES = CCCCCCCCO
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>8</sub>H<sub>18</sub>O
| MolarMass = 130.23 g/mol
| Density = 0.824 g/cm<sup>3</sup>
| MeltingPt = -16 °C
| BoilingPt = 195 °C
}}
}}
'''Octanol''' is a straight chain [[fatty alcohol]] with eight [[carbon]] [[atom]]s and the molecular formula CH<sub>3</sub>(CH<sub>2</sub>)<sub>7</sub>OH. Although the term ''octanol'' usually refers exclusively to the [[primary alcohol]] 1-octanol, there are other less common isomers of octanol such as the [[secondary alcohol]]s 2-octanol, 3-octanol and 4-octanol.
Octanol occurs naturally in the form of [[ester]]s in some essential oils. The primary use of octanol is in the manufacture of various esters (both synthetic and naturally occurring), such as [[octyl acetate]], which are used in perfumery and flavors. Other uses include experimental medical applications utilizing octanol to control Essential Tremor and other types of involuntary neurological tremors.<ref>{{ClinicalTrialsGov|NCT00102596}}</ref>
===Preparation===
Octanol is produced industrially by the oligomerization of [[ethylene]] using [[triethylaluminium]] followed by oxidation of the [[organoaluminium|alkylaluminium products]].<ref name=Falbe>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</ref> An idealized synthesis is shown:
:Al(C<sub>2</sub>H<sub>5</sub>)<sub>3</sub> + 9 C<sub>2</sub>H<sub>4</sub> → Al(C<sub>8</sub>H<sub>17</sub>)<sub>3</sub>
:Al(C<sub>8</sub>H<sub>17</sub>)<sub>3</sub> + 3 O + 3 H<sub>2</sub>O → 3 HOC<sub>8</sub>H<sub>17</sub> + Al(OH)<sub>3</sub>
The process generates a range of alcohols that are separated by [[distillation]].
===Water/ octanol partitioning===
{{see also|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 good approximation of the partitioning between the [[cytosol]] and [[lipid]] [[Biological membrane|membrane]]s of living systems.{{Fact|date=February 2007}}
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
<ref>{{cite journal
| author = McCarley KD, Bunge AL
| title = Pharmacokinetic Models of Dermal Absorption
| journal = Journal of Pharmaceutical Sciences
| volume = 90
| issue = 11
| pages = 1699–1719
| year = 2001
| pmid = 11745728
| doi = 10.1002/jps.1120
}}</ref>:
:<math>\log(K_{sc/w}) = a + b\log(K_{w/o})</math>
Where a and b are constants,<math>K_{sc/w}</math> is the stratum corneum/ water partition coefficient, and<math>K_{o/w}</math> is the water/ octanol partition coefficient. The values of a and b vary between papers, but Cleek & Bunge
<ref>{{cite journal
| author = Cleek RL, Bunge AL
| title = A new method for estimating dermal absorption from chemical exposure. 1. General approach
| journal = Pharmaceutical Research
| volume = 10
| issue = 4
| pages = 497–506
| year = 1993
| pmid = 8483831
| doi = 10.1023/A:1018981515480
}}</ref>
have reported the values a=0, b=0.74.
==References==
<references />
{{Alcohols}}
[[Category:Fatty alcohols]]
[[de:1-Octanol]]
[[it:1-ottanolo]]
[[nl:1-octanol]]
[[ja:オクタノール]]
[[fi:Oktanoli]]