1-Octanol

Octanol
Names
Preferred IUPAC name
Octan-1-ol
Other names
1-Octanol; n-Octanol; Capryl alcohol; Octyl alcohol
Identifiers
3D model (JSmol)
1697461
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.561
EC Number
  • 203-917-6
82528
KEGG
UNII
  • 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
  • CCCCCCCCO
Properties
C8H18O
Molar mass 130.231 g·mol−1
Appearance Colorless liquid[1]
Odor Aromatic[1]
Density 0.83 g/cm3 (20 °C)[1]
Melting point −16 °C (3 °F; 257 K)[1]
Boiling point 195 °C (383 °F; 468 K)[1]
0.3 g/L (20 °C)[1]
Viscosity 7.36 cP[2]
Hazards
GHS labelling:
Warning
H319
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).
N verify (what is YN ?)
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] (grapefruit oil, orange oil, bergamot oil, mandarin oil and lime oil[4]). 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.[5]

Water/octanol partitioning

Main article: Octanol-water 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.[6]

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:[7]

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[8] 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] 1-Octanol hydrogen bonds to Lewis bases. It is a Lewis acid in the ECW model and its acid parameters are EA = 0.85 and C A = 0.87.[9]

Octanol has a sedative and anesthetic effect in animal studies, though 1-octanol may not be the most potent isomer.[10][11][12][13][14][15] 1-Octanol 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 of alcohol intoxication at therapeutic dosages.[16][17]

See also

References

  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 MN (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. ^ a b c Falbe J, Bahrmann H, Lipps W, Mayer D, Frey GD (2013). "Alcohols, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. American Cancer Society. doi:10.1002/14356007.a01_279.pub2. ISBN 978-3527306732.
  4. ^ "Эфирные масла цитрусовых и их химический состав". citrusmasla.ru. Retrieved 2025-10-17.
  5. ^ J. Grub, E. Löser (2012). "Butadiene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_431.pub2. ISBN 978-3-527-30673-2.
  6. ^ Schwarzenbach RP, Gschwend PM, Imboden DM (2003). Environmental organic chemistry. John Wiley. ISBN 0-471-35053-2.
  7. ^ 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.
  8. ^ 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.
  9. ^ Vogel GC, Drago RS (1996). "The ECW Model". Journal of Chemical Education. 73 (8): 701. Bibcode:1996JChEd..73..701V. doi:10.1021/ed073p701. ISSN 0021-9584.
  10. ^ Lyon RC, McComb JA, Schreurs J, Goldstein DB (September 1981). "A relationship between alcohol intoxication and the disordering of brain membranes by a series of short-chain alcohols". The Journal of Pharmacology and Experimental Therapeutics. 218 (3): 669–675. PMID 7264950.
  11. ^ De Fiebre NC, Marley RJ, Wehner JM, Collins AC (October 1992). "Lipid solubility of sedative-hypnotic drugs influences hypothermic and hypnotic responses of long-sleep and short-sleep mice". The Journal of Pharmacology and Experimental Therapeutics. 263 (1): 232–240. PMID 1403788.
  12. ^ Kurata Y, Marszalec W, Hamilton BJ, Carter DB, Narahashi T (December 1993). "Alcohol modulation of cloned GABAA receptor-channel complex expressed in human kidney cell lines". Brain Research. 631 (1): 143–146. doi:10.1016/0006-8993(93)91200-c. PMID 7507787.
  13. ^ Todorovic SM, Lingle CJ (January 1998). "Pharmacological properties of T-type Ca2+ current in adult rat sensory neurons: effects of anticonvulsant and anesthetic agents". Journal of Neurophysiology. 79 (1): 240–252. doi:10.1152/jn.1998.79.1.240. PMID 9425195.
  14. ^ Lobo IA, Mascia MP, Trudell JR, Harris RA (August 2004). "Channel gating of the glycine receptor changes accessibility to residues implicated in receptor potentiation by alcohols and anesthetics". The Journal of Biological Chemistry. 279 (32): 33919–33927. doi:10.1074/jbc.M313941200. PMID 15169788.
  15. ^ Li GD, Chiara DC, Cohen JB, Olsen RW (March 2010). "Numerous classes of general anesthetics inhibit etomidate binding to gamma-aminobutyric acid type A (GABAA) receptors". The Journal of Biological Chemistry. 285 (12): 8615–8620. doi:10.1074/jbc.M109.074708. PMC 2838283. PMID 20083606.
  16. ^ Bushara KO, Goldstein SR, Grimes GJ, Burstein AH, Hallett M (January 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.
  17. ^ Nahab FB, Wittevrongel L, Ippolito D, Toro C, Grimes GJ, Starling J, et al. (October 2011). "An open-label, single-dose, crossover study of the pharmacokinetics and metabolism of two oral formulations of 1-octanol in patients with essential tremor". Neurotherapeutics. 8 (4): 753–762. doi:10.1007/s13311-011-0045-1. PMC 3250299. PMID 21594724.
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