1-Octanol

Octanol
Names
	Preferred IUPAC name Octan-1-ol
	Other names 1-Octanol; n-Octanol; Capryl alcohol; Octyl alcohol
Identifiers
CAS Number	111-87-5 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1697461
ChEBI	CHEBI:16188;
ChEMBL	ChEMBL26215 ;
ChemSpider	932 ;
ECHA InfoCard	100.003.561
EC Number	203-917-6;
Gmelin Reference	82528
IUPHAR/BPS	4278;
KEGG	C00756;
PubChem CID	957;
UNII	NV1779205D ;
CompTox Dashboard (EPA)	DTXSID7021940 ;
	InChI InChI=1S/C8H18O/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3 Key: KBPLFHHGFOOTCA-UHFFFAOYSA-N ; InChI=1/C8H18O/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3 Key: KBPLFHHGFOOTCA-UHFFFAOYAH;
	SMILES CCCCCCCCO;
Properties
Chemical formula	C8H18O
Molar mass	130.231 g·mol−1
Appearance	Colorless liquid
Odor	Aromatic
Density	0.83 g/cm3 (20 °C)
Melting point	−16 °C (3 °F; 257 K)
Boiling point	195 °C (383 °F; 468 K)
Solubility in water	0.3 g/L (20 °C)
Viscosity	7.36 cP
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319
Precautionary statements	P264, P280, P305+P351+P338, P337+P313
NFPA 704 (fire diamond)	1 2 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.^[3] It is used to evaluate the lipophilicity of pharmaceutical products.

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Octanol is mainly 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.^[3] 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 can be separated by distillation.

The Kuraray process defines an alternative route to 1-octanol, but using C4 + C4 building strategy. 1,3-Butadiene is dimerized concomitant with the addition of one molecule of water. This conversion is catalyzed by palladium complexes. The resulting doubly unsaturated alcohol is then hydrogenated.^[4]

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.^[5]

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:^[6]

\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^[7] have reported the values a = 0, b = 0.74.

With a flash point of 81 °C, 1-octanol is not seriously flammable, though its autoignition temperature is as low as 245 °C. 1-Octanol is mainly consumed as a precursor to perfumes.^[3] It has been examined for controlling essential tremor and other types of involuntary neurological tremors because evidence indicates it can relieve tremor symptoms at lower doses than are required to obtain a similar level of symptomatic relief from consumption of ethanol, thereby reducing the risk alcohol intoxication at therapeutic dosages.^[8]

1-Octanol hydrogen bonds to Lewis bases. It is a Lewis acid in the ECW model and its acid parameters are E_A = 0.85 and C _A = 0.87.^[9]

2-Octanol

[1]
Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
[2]
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.
[3]
Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter; Frey, Guido D. (2013). "Alcohols, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. American Cancer Society. doi:10.1002/14356007.a01_279.pub2. ISBN 978-3527306732.
[4]
J. Grub; E. Löser (2012). "Butadiene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_431.pub2. ISBN 978-3527306732.
[5]
Schwarzenbach, Rene P.; Gschwend, Philip M.; Imboden, Dieter M. (2003). Environmental organic chemistry. John Wiley. ISBN 0-471-35053-2.
[6]
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.
[7]
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. S2CID 24534572.
[8]
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. S2CID 9015641.
[9]
Vogel, Glenn C.; Drago, Russell S. (1996). "The ECW Model". Journal of Chemical Education. 73 (8): 701. Bibcode:1996JChEd..73..701V. doi:10.1021/ed073p701. ISSN 0021-9584.

[GESTIS-1] [1]
Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[2] [2]
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.

[Falbe-3] [3]
Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter; Frey, Guido D. (2013). "Alcohols, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. American Cancer Society. doi:10.1002/14356007.a01_279.pub2. ISBN 978-3527306732.

[Ullmann-4] [4]
J. Grub; E. Löser (2012). "Butadiene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_431.pub2. ISBN 978-3527306732.

[5] [5]
Schwarzenbach, Rene P.; Gschwend, Philip M.; Imboden, Dieter M. (2003). Environmental organic chemistry. John Wiley. ISBN 0-471-35053-2.

[6] [6]
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.

[7] [7]
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. S2CID 24534572.

[8] [8]
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. S2CID 9015641.

[9] [9]
Vogel, Glenn C.; Drago, Russell S. (1996). "The ECW Model". Journal of Chemical Education. 73 (8): 701. Bibcode:1996JChEd..73..701V. doi:10.1021/ed073p701. ISSN 0021-9584.

[3]

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1-Octanol

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Preparation

Water/octanol partitioning

Properties and uses

See also

References