Octanol 542972 222859617 2008-07-01T13:38:20Z DOI bot 6652755 Citation maintenance. Formatted: title. You can [[WP:DOI|use this bot]] yourself! Please [[User:DOI_bot/bugs|report any bugs]]. {{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]]