1-Octanol

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Octanol


IUPAC name Octan-1-ol
Other names 1-Octanol; Capryl alcohol; Octyl alcohol
Identifiers
CAS number	111-87-5^Y
PubChem	957
ChemSpider	932^N
ChEMBL	CHEMBL26215^N
Jmol-3D images	Image 1
SMILES CCCCCCCCO
InChI InChI=1S/C8H18O/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3^N Key: KBPLFHHGFOOTCA-UHFFFAOYSA-N^N InChI=1/C8H18O/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3 Key: KBPLFHHGFOOTCA-UHFFFAOYAH
Properties
Molecular formula	C₈H₁₈O
Molar mass	130.23 g mol⁻¹
Density	0.824 g/cm³
Melting point	−16 °C; 3 °F; 257 K
Boiling point	195 °C; 383 °F; 468 K
Solubility in water	0.460 g/liter^[1]
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

1-Octanol is the organic compound with the molecular formula CH₃(CH₂)₇OH. It is a fatty alcohol. Many other isomers are also known generically as octanols. 1-Octanol is manufactured for the synthesis of esters for use in perfumes and flavorings. Esters of octanol, such as octyl acetate, occur as components of essential oils.^[2] It is used to evaluate the lipophilicity of pharmaceutical products.

Preparation

Octanol is produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products. This route is known as the Ziegler alcohol synthesis.^[2] An idealized synthesis is shown:

Al(C₂H₅)₃ + 9 C₂H₄ → Al(C₈H₁₇)₃

Al(C₈H₁₇)₃ + 3 O + 3 H₂O → 3 HOC₈H₁₇ + Al(OH)₃

The process generates a range of alcohols, which are separated by distillation.

Water/octanol partitioning

Main article: 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 relatively good approximation of the partitioning between the cytosol and lipid membranes of living systems.^[3]

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:^[4]

$\log(K_{{sc/w}})=a+b\log(K_{{w/o}})$

Where a and b are constants, $K_{{sc/w}}$ is the stratum corneum/ water partition coefficient, and $K_{{w/o}}$ is the water/ octanol partition coefficient. The values of a and b vary between papers, but Cleek & Bunge^[5] have reported the values a=0, b=0.74.

Uses

1-Octanol is mainly consumed as a precursor to perfumes.^[2] It has been examined for controlling Essential Tremor and other types of involuntary neurological tremors.^[6]

References

↑ Lide, D. R., ed. (2013-2014). CRC Handbook of Chemistry and Physics (94th ed.). Boca Raton (FL): CRC Press.
↑ 2.0 2.1 2.2 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
↑ Schwarzenbach, Rene P.; Gschwend, Philip M.; Imboden, Dieter M. (2003). Environmental organic chemistry. John Wiley. ISBN 0-471-35053-2.
↑ McCarley KD, Bunge AL (2001). "Pharmacokinetic Models of Dermal Absorption". Journal of Pharmaceutical Sciences 90 (11): 1699–1719. doi:10.1002/jps.1120. PMID 11745728.
↑ Cleek RL, Bunge AL (1993). "A new method for estimating dermal absorption from chemical exposure. 1. General approach". Pharmaceutical Research 10 (4): 497–506. doi:10.1023/A:1018981515480. PMID 8483831.
↑ Bushara K. et al. (2004). "Pilot trial of 1-octanol in essential tremor". Neurology 62 (1): 122–124. PMID 14718713.

v t e Alcohols

Straight-chain primary alcohols (1°)	Methanol (C 1) Ethanol (C 2) 1-Propanol (C 3) n-Butanol (C 4) 1-Pentanol (C 5) 1-Hexanol (C 6) 1-Heptanol (C 7) 1-Octanol (C 8) 1-Nonanol (C 9) 1-Decanol (C 10) Undecanol (C 11) Dodecanol (C 12) Tridecan-1-ol (C 13) 1-Tetradecanol (C 14) Pentadecan-1-ol (C 15) Cetyl alcohol (C 16) Heptadecan-1-ol (C 17) Stearyl alcohol (C 18) Nonadecan-1-ol (C 19) Arachidyl alcohol (C 20) Heneicosan-1-ol (C 21) Docosanol (C 22) Tricosan-1-ol (C 23) 1-Tetracosanol (C 24) Pentacosan-1-ol (C 25) 1-Hexacosanol (C 26) 1-Heptacosanol (C 27) 1-Octacosanol (C 28) 1-Nonacosanol (C 29) Triacontanol (C 30) Policosanol

Other primary alcohols	Isobutanol (C 4) Isoamyl alcohol (C 5)

Secondary alcohols (2°)	Isopropanol (C 3) 2-Butanol (C 4) 2-Pentanol (C 5) 2-Hexanol (C 6) 2-Heptanol (C 7) 2-Methyl-1-butanol (C 5) Cyclohexanol (C 6)

Tertiary alcohols (3°)	tert-Butyl alcohol (C 4) tert-Amyl alcohol (C 5) 2-Methyl-2-pentanol (C 6) 2-Methylhexan-2-ol (C 7) 2-Methylheptan-2-ol (C 8) 3-Methyl-3-pentanol (C 6) 3-Methyloctan-3-ol (C 9)

Biochemical families: carbohydrates alcohols glycoproteins glycosides lipids eicosanoids fatty acids / intermediates phospholipids sphingolipids steroids nucleic acids constituents / intermediates proteins Amino acids / intermediates tetrapyrroles / intermediates

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