Octanol: Difference between revisions

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			{{Short description\|Group of isomers}}
	{{chembox
			{{Distinguish\|octanal\|octanyl\|octanoyl\|octenol\|octynol\|Octonal (disambiguation){{!}}octonal}}
	\| verifiedrevid = 311135632
			'''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>
	\| Name = '''Octanol'''
	\| ImageFile = 1-Octanol.png
	\| ImageSize = 220px
	\| ImageName = Skeletal formula
	\| ImageFile1 = 1-Octanol-3D-vdW.png
	\| ImageName1 = Space-filling model
	\| IUPACName = Octan-1-ol
	\| OtherNames = capryl alcohol<br />octyl alcohol
	\| Section1 = {{Chembox Identifiers
	\| CASNo_Ref = {{cascite}}
	\| 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>
	\| Solubility = Insoluble
	\| 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> Bushara K. etal Pilot trial of 1-octanol in essential tremor” Neurology 2004; 62:122-4</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. <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 <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_{w/o}</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}}		{{Alcohols}}
			{{Authority control}}

	]		]
			]

⚫	]
	]
	]
	]
	]
	]
⚫	]
	]
	]

Latest revision as of 01:10, 4 July 2024

Group of isomers Not to be confused with octanal, octanyl, octanoyl, octenol, octynol, or octonal.

Octanols are alcohols with the formula C₈H₁₇OH. A simple and important member is 1-octanol, with an unbranched chain of carbons. Other commercially important octanols are 2-octanol and 2-ethylhexanol. Some octanols occur naturally in the form of esters in some essential oils.

Isomers

There are 89 possible isomers of octanol, including:

References

"Octanol". Human Metabolome Database. Retrieved 29 December 2019.

Alcohols

By consumption

Alcohols found in alcoholic drinks	1-Propanol 2-Methyl-1-butanol Ethanol Isoamyl alcohol Isobutanol Phenethyl alcohol tert-Amyl alcohol tert-Butyl alcohol Tryptophol
Medical alcohol	Ethchlorvynol Methylpentynol Methanol poisoning Ethanol
Toxic alcohols	Isopropyl alcohol Methanol

Primary
alcohols (1°)

Methanol	4-Methylcyclohexanemethanol Aminomethanol Cyclohexylmethanol Methoxymethanol Methylazoxymethanol Trifluoromethanol
Ethanol	1-Aminoethanol 2,2,2-Trichloroethanol 2,2,2-Trifluoroethanol 2-(2-Ethoxyethoxy)ethanol 2-(2-Methoxyethoxy)ethanol 2-(2-Methoxyethoxy)ethanol 2-Butoxyethanol 2-Chloroethanol 2-Ethoxyethanol 2-Fluoroethanol 2-Mercaptoethanol 2-Methoxyethanol Aminoethylethanolamine Diethylethanolamine Dimethylethanolamine Ethanol Ethanolamine N,N-Diisopropylaminoethanol N-Methylethanolamine Phenoxyethanol Tribromoethanol
Butanol	2-Methyl-1-butanol Isobutanol n-Butanol
Straight-chain saturated C₁ — C₉	Methanol Ethanol 1-Propanol 1-Butanol 1-Pentanol 1-Hexanol 1-Heptanol 1-Octanol (capryl) 1-Nonanol (pelargonic)
Straight-chain saturated C₁₀ — C₁₉	1-Decanol (capric) 1-Undecanol (hendecyl) 1-Dodecanol (lauryl) 1-Tridecanol 1-Tetradecanol (myristyl) 1-Pentadecanol 1-Hexadecanol (cetyl / palmityl) 1-Heptadecanol 1-Octadecanol (stearyl) 1-Nonadecanol
Straight-chain saturated C₂₀ — C₂₉	1-Icosanol (arachidyl) 1-Heneicosanol 1-Docosanol (behenyl) 1-Tricosanol 1-Tetracosanol (lignoceryl) 1-Pentacosanol 1-Hexacosanol (ceryl) 1-Heptacosanol 1-Octacosanol (cluytyl / montanyl) 1-Nonacosanol
Straight-chain saturated C₃₀ — C₃₉	1-Triacontanol (melissyl / myricyl) 1-Hentriacontanol 1-Dotriacontanol (lacceryl) 1-Tritriacontanol 1-Tetratriacontanol (geddyl) 1-Pentatriacontanol 1-Hexatriacontanol 1-Heptatriacontanol 1-Octatriacontanol 1-Nonatriacontanol
Straight-chain saturated C₄₀ — C₄₉	1-Tetracontanol 1-Hentetracontanol 1-Dotetracontanol 1-Tritetracontanol 1-Tetratetracontanol 1-Pentatetracontanol 1-Hexatetracontanol 1-Heptatetracontanol 1-Octatetracontanol 1-Nonatetracontanol

Secondary
alcohols (2°)

Propylene glycol methyl ether

Tertiary
alcohols (3°)

Hydric alcohols

Monohydric alcohols	Methanol (C₁) Ethanol (C₂) Isopropanol (C₃) 1-Butanol (C₄) 1-Pentanol (C₅) Cetyl alcohol (C₁₆)
Dihydric alcohols	Ethylene glycol Propylene glycol
Trihydric alcohols	Glycerol
Polyhydric alcohols (sugar alcohols)	Pentaerythritol Ethylene glycol (C₂) Glycerol, Propylene glycol (C₃) Erythritol, Threitol (C₄) Xylitol (C₅) Mannitol, Sorbitol (C₆) Volemitol (C₇)

Amyl alcohols

Aromatic alcohols

Saturated
fatty alcohols

Branched and
unsaturated
fatty alcohols

Sugar alcohols

C₁ — C₇	Methylene glycol (C₁) Ethylene glycol (C₂) Glycerol (C₃) Erythritol (C₄) Threitol (C₄) Arabitol (C₅) Ribitol (C₅) Xylitol (C₅) Mannitol (C₆) Sorbitol (C₆) Galactitol (C₆) Iditol (C₆) Volemitol (C₇)
Deoxy sugar alcohols	Fucitol
Cyclic sugar alcohols	Inositol
Glycylglycitols	Maltitol Lactitol Isomalt Maltotriitol Maltotetraitol Polyglycitol

Terpene alcohols

Monoterpene alcohols	Borneol Citronellol Geraniol Linalool Menthol Nerol Rhodinol Terpineol
Sesquiterpene alcohols	Bisabolol Farnesol Nerolidol Patchoulol
Diterpene alcohols	Phytol

Dialcohols

Trialcohols

Glycerol

Sterols

Fluoroalcohols

Preparations

Reactions

Category

Categories:

Latest revision as of 01:10, 4 July 2024

Isomers

See also

References