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.

Preparation

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]

Water/octanol partitioning

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.

Properties and uses

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]

References

^ ^a ^b ^c ^d ^e ^f Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
^ 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 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.
^ 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.
^ 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. S2CID 24534572.
^ 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.
^ 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] ^ ^a ^b ^c ^d ^e ^f 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.

[Falbe-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] 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.

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Preparation

Water/octanol partitioning

Properties and uses

See also

References