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Revision as of 19:36, 31 August 2009 editHelgiII (talk | contribs)35 editsNo edit summary← Previous edit Latest revision as of 01:10, 4 July 2024 edit undoTeaktl17 (talk | contribs)Extended confirmed users18,034 edits top: Not to be confused with: + octanyl, octanoyl, octynol 
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{{Short description|Group of isomers}}
{{chembox
{{Distinguish|octanal|octanyl|octanoyl|octenol|octynol|Octonal (disambiguation){{!}}octonal}}
| Name = '''Octanol'''
'''Octanols''' are ] with the formula C<sub>8</sub>H<sub>17</sub>OH. A simple and important member is ], with an unbranched chain of carbons. Other commercially important octanols are ] and ]. Some octanols occur naturally in the form of ]s in some essential oils.<ref>{{cite web |title=Octanol |url=http://www.hmdb.ca/metabolites/HMDB0001183 |website=Human Metabolome Database |access-date=29 December 2019}}</ref>
| ImageFile = 1-Octanol.png
| ImageSize = 200px
| ImageName = 1-Octanol
| IUPACName = Octan-1-ol
| OtherNames = capryl alcohol<br />octyl alcohol
| Section1 = {{Chembox Identifiers
| CASNo = 111-87-5
| SMILES = CCCCCCCCO
| PubChem = 957
}}
| 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>
| MeltingPtC = -16
| BoilingPtC = 195
}}
}}


==Isomers==
'''Octanol''' is a straight chain ] with eight ] ]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 ] 1-octanol, there are other less common isomers of octanol such as the ]s 2-octanol, 3-octanol and 4-octanol.


There are 89 possible ]s of octanol,{{citation needed|date=March 2015}} including:
Octanol occurs naturally in the form of ]s in some essential oils. The primary use of octanol is in the manufacture of various esters (both synthetic and naturally occurring), such as ], 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 ] using ] followed by oxidation of the ].<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 ].


==See also==
==Water/octanol partitioning==
*]
{{see also|Partition coefficient}}
Octanol and ] are ]. The distribution of a compound between water and octanol is used to calculate the ] '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 ] and ] ]s of living systems.&nbsp;<ref>{{Cite book
| last1 = Schwarzenbach | first1 = Rene P.
| last2 = Gschwend | first2 = Philip M.
| last3 = Imboden | first3 = Dieter M.
| title = ]
| publisher = ]
| year = 2003
| isbn = 0471350532 }}
</ref>


==References==
Many dermal absorption models consider the ]/ water partition coefficient to be well approximated by a function of the water/ octanol partition coefficient of the form&nbsp;<ref>{{cite journal
{{Reflist}}
| 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&nbsp;<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}} {{Alcohols}}
{{Authority control}}


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