Octanol


Octanol
Octanol
Identifiers
CAS number 111-87-5 YesY
PubChem 957
ChEMBL CHEMBL26215 N
Jmol-3D images Image 1
Properties
Molecular formula C8H18O
Molar mass 130.23 g mol−1
Density 0.824 g/cm3
Melting point

-16 °C, 257 K, 3 °F

Boiling point

195 °C, 468 K, 383 °F

Solubility in water Insoluble
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Octanol is a straight chain fatty alcohol with eight carbon atoms and the molecular formula CH3(CH2)7OH. Although the term octanol usually refers exclusively to the primary alcohol 1-octanol, there are other less common isomers of octanol such as the secondary alcohols 2-octanol, 3-octanol and 4-octanol.

Octanol occurs naturally in the form of esters in some essential oils. The primary use of octanol is in the manufacture of various esters (both synthetic and naturally occurring), such as octyl acetate, which are used in perfumery and flavors. Other uses include experimental medical applications utilizing octanol to control Essential Tremor and other types of involuntary neurological tremors.[1]

Preparation

Octanol is produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products.[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 that are separated by distillation.

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.[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]

log(Ksc / w) = a + blog(Kw / o)

Where a and b are constants,Ksc / w is the stratum corneum/ water partition coefficient, andKw / o 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.

References

  1. ^ Bushara K. et al. (2004). "Pilot trial of 1-octanol in essential tremor". Neurology 62 (1): 122–124. PMID 14718713. 
  2. ^ 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
  3. ^ Schwarzenbach, Rene P.; Gschwend, Philip M.; Imboden, Dieter M. (2003). Environmental organic chemistry. John Wiley. ISBN 0471350532. 
  4. ^ 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. 
  5. ^ 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. 



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Look at other dictionaries:

  • Octanol — Général Nom IUPAC 1 octanol Synonymes Alcool caprylique …   Wikipédia en Français

  • octanol — [äk′tə nôl΄, äk′tənōl΄] n. 〚 OCTAN(E) + OL1〛 any of four colorless, liquid alcohols, C8H17OH, used in perfumery and as solvents, foam control agents, etc. * * * …   Universalium

  • octanol — sustantivo masculino 1. (no contable) Área: química Alcohol oleoso y aromático derivado del octano, que se utiliza en productos de limpieza y en perfumería …   Diccionario Salamanca de la Lengua Española

  • octanol — [äk′tə nôl΄, äk′tənōl΄] n. [ OCTAN(E) + OL1] any of four colorless, liquid alcohols, C8H17OH, used in perfumery and as solvents, foam control agents, etc …   English World dictionary

  • Octanol — Strukturformel Allgemeines Name 1 Octanol Andere Namen 1 Octanol n Octanol Octan 1 ol Octylalkohol Caprylalkohol …   Deutsch Wikipedia

  • Octanol — Un octanol es un alcohol monosustituido con 8 átomos de carbono unidos por enlaces covalentes sencillos y un sólo grupo OH. Su formula molecular es C8H18O[1] y masa molecular 130,23 g/mol . El más importante de la familia es el octan 1 ol… …   Wikipedia Español

  • octanol — ˈäktəˌnȯl, nōl noun ( s) Etymology: octane + ol : any of four liquid alcohols C8H17OH derived from normal octane: as a. : the primary alcohol CH3(CH2)6CH2OH having a penetrating odor, occurring free or in the form of esters in oils from plant… …   Useful english dictionary

  • octanol — noun Any of many isomers of the saturated aliphatic alcohol having eight carbon atoms, but especially the simple primary alcohol n octanol; its esters are used in perfumery …   Wiktionary

  • Octanol — Oc|ta|nol, eigtl. Octan 1 ol [↑ Octan u. ↑ ol (1)], das; s; veraltete Syn.: n Octanol, Octylalkohol, Caprylalkohol: C7H15 CH2OH; farblose Fl., Sdp. 195 °C, die als Lsgm. u. Zwischenprodukt für Synthesen benutzt wird. Im Fachjargon bezeichnet man… …   Universal-Lexikon

  • octanol — oc·ta·nol …   English syllables


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