1-Octanol
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| Names | |
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| IUPAC name
Octan-1-ol
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| Other names
1-Octanol; Capryl alcohol; Octyl alcohol
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| Identifiers | |
111-87-5  |
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| 3D model (Jmol) | Interactive image |
| ChEMBL | ChEMBL26215  |
| ChemSpider | 932 |
| ECHA InfoCard | 100.003.561 |
| 4278 | |
| PubChem | 957 |
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| Properties | |
| 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) |
| 0.46 g/liter | |
| Viscosity | 7.36 cP (at 25 °C)[1] |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |
1-Octanol also known as Octan-1-ol 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. It has a pungent odor. 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[edit]
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[edit]
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]
Where a and b are constants, is the stratum corneum/ water partition coefficient, and 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[edit]
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]
See also[edit]
References[edit]
- ^ Bhattacharjee, A.; Roy, M. N. (2010-11-17). "Density, Viscosity, and Speed of Sound of (1-Octanol + 2-Methoxyethanol),(1-Octanol + N,N-Dimethylacetamide), and (1-Octanol + Acetophenone) at Temperatures of (298.15, 308.15, and 318.15) K". Journal of Chemical & Engineering Data. 55 (12): 5914–5920. doi:10.1021/je100170v.
- ^ a b c 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. doi:10.1212/01.wnl.0000101722.95137.19. PMID 14718713.
