1-Octanol

vanc 6 changed changed 377204105 Octanol 1-Octanol.svg 300px Skeletal formula skin-invert 1-Octanol-3D-vdW.png Space-filling model bg-transparent Octan-1-ol 1-Octanoln-OctanolCapryl alcoholOctyl alcohol 4278 correct CAS 111-87-5 OcOHn-OcOHnOcOHnOcOH correct FDA NV1779205D 16188 correct EBI 26215 CCCCCCCCO 957 1697461 82528 C00756 203-917-6 correct chemspider 932 1/C8H18O/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3 KBPLFHHGFOOTCA-UHFFFAOYAH changed chemspider 1S/C8H18O/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3 changed chemspider KBPLFHHGFOOTCA-UHFFFAOYSA-N 8 18 1 0.83 g/cm3 (20 °C)37840 Colorless liquid Aromatic 0.3 g/L (20 °C) 7.36cP Bhattacharjee A, Roy MN 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 2010-11-17 10.1021/je100170v -16 195 07 Warning 319 264 280 305+351+338 337+313 2 1 0 1-Octanol, also known as octan-1-ol or simply octanol, is the organic compound with the molecular formula C8H18O 1 or 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 (grapefruit oil, orange oil, bergamot oil, mandarin oil and lime oilЭфирные масла цитрусовых и их химический состав https://citrusmasla.ru/ 2025-10-17 citrusmasla.ru). 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.Falbe Jürgen Bahrmann Helmut Lipps Wolfgang Mayer Dieter Frey Guido D. Alcohols, Aliphatic Ullmann's Encyclopedia of Industrial Chemistry 2013 10.1002/14356007.a01_279.pub2 978-3527306732 American Cancer Society en 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.Butadiene J. Grub E. Löser 2012 10.1002/14356007.a04_431.pub2 Water/octanol partitioning 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. Schwarzenbach Rene P. Gschwend Philip M. Imboden Dieter M. Environmental organic chemistry John Wiley 2003 0-471-35053-2 Environmental organic chemistry 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: McCarley KD, Bunge AL Pharmacokinetic Models of Dermal Absorption Journal of Pharmaceutical Sciences 90 11 1699–1719 2001 11745728 10.1002/jps.1120 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 Cleek RL, Bunge AL A new method for estimating dermal absorption from chemical exposure. 1. General approach Pharmaceutical Research 10 4 497–506 1993 8483831 10.1023/A:1018981515480 24534572 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. 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 CA = 0.87.Vogel Glenn C. Drago Russell S. 1996 The ECW Model https://pubs.acs.org/doi/abs/10.1021/ed073p701 Journal of Chemical Education en 73 8 701 10.1021/ed073p701 1996JChEd..73..701V 0021-9584 subscription Octanol has a sedative and anesthetic effect in animal studies, though 1-octanol may not be the most potent isomer. Lyon RC, McComb JA, Schreurs J, Goldstein DB 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 September 1981 7264950 De Fiebre NC, Marley RJ, Wehner JM, Collins AC 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 October 1992 1403788 Kurata Y, Marszalec W, Hamilton BJ, Carter DB, Narahashi T Alcohol modulation of cloned GABAA receptor-channel complex expressed in human kidney cell lines Brain Research 631 1 143–146 December 1993 7507787 10.1016/0006-8993(93)91200-c Todorovic SM, Lingle CJ 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 January 1998 9425195 10.1152/jn.1998.79.1.240 Lobo IA, Mascia MP, Trudell JR, Harris RA 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 August 2004 15169788 10.1074/jbc.M313941200 free Li GD, Chiara DC, Cohen JB, Olsen RW 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 March 2010 20083606 10.1074/jbc.M109.074708 free 2838283 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. Bushara KO, Goldstein SR, Grimes GJ, Burstein AH, Hallett M Pilot trial of 1-octanol in essential tremor Neurology 62 1 122–124 January 2004 14718713 10.1212/01.wnl.0000101722.95137.19 9015641 Nahab FB, Wittevrongel L, Ippolito D, Toro C, Grimes GJ, Starling J, Potti G, Haubenberger D, Bowen D, Buchwald P, Dong C, Kalowitz D, Hallett M 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 October 2011 21594724 3250299 10.1007/s13311-011-0045-1 See also 2-Octanol References Category:Fatty alcohols Category:Primary alcohols Category:Octanols