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{{Short description|Group of isomers}} |
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{{chembox |
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{{Distinguish|octanal|octanyl|octanoyl|octenol|octynol|Octonal (disambiguation){{!}}octonal}} |
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| Name = '''Octanol''' |
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'''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> |
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| ImageFile = 1-Octanol.png |
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| ImageSize = 200px |
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| ImageName = 1-Octanol |
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| IUPACName = Octan-1-ol |
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| OtherNames = capryl alcohol<br />octyl alcohol |
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| Section1 = {{Chembox Identifiers |
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| CASNo = 111-87-5 |
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| SMILES = CCCCCCCCO |
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| PubChem = 957 |
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}} |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>8</sub>H<sub>18</sub>O |
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| MolarMass = 130.23 g/mol |
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| Density = 0.824 g/cm<sup>3</sup> |
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| MeltingPtC = -16 |
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| BoilingPtC = 195 |
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}} |
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}} |
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==Isomers== |
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'''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. |
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There are 89 possible ]s of octanol,{{citation needed|date=March 2015}} including: |
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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> |
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*] |
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==Preparation== |
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*] |
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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: |
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*] |
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: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> |
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: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> |
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The process generates a range of alcohols that are separated by ]. |
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==See also== |
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==Water/octanol partitioning== |
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{{see also|Partition coefficient}} |
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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. <ref>{{Cite book |
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| last1 = Schwarzenbach | first1 = Rene P. |
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| last2 = Gschwend | first2 = Philip M. |
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| last3 = Imboden | first3 = Dieter M. |
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| title = ] |
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| publisher = ] |
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| year = 2003 |
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| isbn = 0471350532 }} |
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</ref> |
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==References== |
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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 <ref>{{cite journal |
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{{Reflist}} |
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| author = McCarley KD, Bunge AL |
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| title = Pharmacokinetic Models of Dermal Absorption |
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| journal = Journal of Pharmaceutical Sciences |
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| volume = 90 |
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| issue = 11 |
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| pages = 1699–1719 |
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| year = 2001 |
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| pmid = 11745728 |
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| doi = 10.1002/jps.1120 |
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}}</ref>: |
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:<math>\log(K_{sc/w}) = a + b\log(K_{w/o})</math> |
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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 |
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| author = Cleek RL, Bunge AL |
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| title = A new method for estimating dermal absorption from chemical exposure. 1. General approach |
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| journal = Pharmaceutical Research |
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| volume = 10 |
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| issue = 4 |
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| pages = 497–506 |
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| year = 1993 |
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| pmid = 8483831 |
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| doi = 10.1023/A:1018981515480 |
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}}</ref> |
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have reported the values a=0, b=0.74. |
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==References== |
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<references /> |
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{{Alcohols}} |
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{{Alcohols}} |
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{{Authority control}} |
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] |
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] |
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