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Wikipedia

1-Octanol

January 01, 1970

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.

Octanol
Names
Preferred IUPAC name
Octan-1-ol
Other names
1-Octanol; n-Octanol; Capryl alcohol; Octyl alcohol
Identifiers
  • 111-87-5 Y
3D model (JSmol)
  • Interactive image
1697461
ChEBI
  • CHEBI:16188
ChEMBL
  • ChEMBL26215 Y
ChemSpider
  • 932 Y
ECHA InfoCard 100.003.561
EC Number
  • 203-917-6
82528
  • 4278
KEGG
  • C00756
  • 957
UNII
  • NV1779205D Y
  • DTXSID7021940
  • 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)
Health 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 YN ?)

Preparation edit

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 edit

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 edit

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 EA = 0.85 and C A = 0.87.[9]

See also edit

References edit

  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.
  3. ^ 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.
  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.

January 01, 1970
octanol, also, known, octan, organic, compound, with, molecular, formula, fatty, alcohol, many, other, isomers, also, known, generically, octanols, manufactured, synthesis, esters, perfumes, flavorings, pungent, odor, esters, octanol, such, octyl, acetate, occ. 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 Octanol Names Preferred IUPAC name Octan 1 ol Other names 1 Octanol n Octanol Capryl alcohol Octyl alcohol Identifiers CAS Number 111 87 5 Y 3D model JSmol Interactive image Beilstein Reference 1697461 ChEBI CHEBI 16188 ChEMBL ChEMBL26215 Y ChemSpider 932 Y ECHA InfoCard 100 003 561 EC Number 203 917 6 Gmelin Reference 82528 IUPHAR BPS 4278 KEGG C00756 PubChem CID 957 UNII NV1779205D Y CompTox Dashboard EPA DTXSID7021940 InChI InChI 1S C8H18O c1 2 3 4 5 6 7 8 9 h9H 2 8H2 1H3 NKey KBPLFHHGFOOTCA UHFFFAOYSA N NInChI 1 C8H18O c1 2 3 4 5 6 7 8 9 h9H 2 8H2 1H3Key KBPLFHHGFOOTCA UHFFFAOYAH SMILES CCCCCCCCO Properties Chemical formula C 8H 18O 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 Solubility in water 0 3 g L 20 C 1 Viscosity 7 36 cP 2 Hazards GHS labelling Pictograms Signal word Warning Hazard statements H319 Precautionary statements P264 P280 P305 P351 P338 P337 P313 NFPA 704 fire diamond 120 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Preparation 2 Water octanol partitioning 3 Properties and uses 4 See also 5 ReferencesPreparation editOctanol 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 editMain 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 log K s c w a b log K w o displaystyle log K sc w a b log K w o nbsp Where a and b are constants K s c w displaystyle K sc w nbsp is the stratum corneum water partition coefficient and K w o displaystyle K w o nbsp is the water octanol partition coefficient The values of a and b vary between papers but Cleek amp Bunge 7 have reported the values a 0 b 0 74 Properties and uses editWith 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 EA 0 85 and C A 0 87 9 See also edit2 OctanolReferences edit 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 amp Engineering Data 55 12 5914 5920 doi 10 1021 je100170v a b c Falbe Jurgen 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 Loser 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 Retrieved from https en wikipedia org w index php title 1 Octanol amp oldid 1194911274, wikipedia, 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