1-Octanol

Source: Wikipedia, the free encyclopedia.
Octanol
Skeletal formula
Space-filling model
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 Edit this at Wikidata
EC Number
  • 203-917-6
82528
IUPHAR/BPS
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:
GHS07: Exclamation mark
Warning
H319
P264, P280, P305+P351+P338, P337+P313
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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 checkY☒N ?)

1-Octanol, also known as octan-1-ol, is 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

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

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.[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]

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[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

Lewis acid in the ECW model and its acid parameters are EA = 0.85 and C A = 0.87.[9]

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. doi:10.1021/je100170v
    .
  3. ^
    ISBN 978-3527306732
    .
  4. ISBN 978-3527306732
    .
  5. ISBN 0-471-35053-2
    .
  6. PMID 11745728
    .
  7. S2CID 24534572
    .
  8. S2CID 9015641
    .
  9. ISSN 0021-9584
    .
Retrieved from "https://en.wikipedia.org/w/index.php?title=1-Octanol&oldid=1194911274"