| Revision as of 23:08, 4 August 2010 edit98.196.25.36 (talk) →Water/octanol partitioning← Previous edit | Revision as of 18:36, 17 March 2011 edit undoEdgar181 (talk | contribs)Extended confirmed users196,325 edits copyediting and minor cleanupNext edit → | ||
| Line 1: | Line 1: | ||
| {{chembox | {{chembox | ||
| | verifiedrevid = 311135632 | | verifiedrevid = 311135632 | ||
| | Name = |
| Name = Octanol | ||
| | ImageFile = 1-Octanol. |
| ImageFile = 1-Octanol.svg | ||
| | ImageSize = 220px | | ImageSize = 220px | ||
| | ImageName = Skeletal formula | | ImageName = Skeletal formula | ||
| Line 8: | Line 8: | ||
| | ImageName1 = Space-filling model | | ImageName1 = Space-filling model | ||
| | IUPACName = Octan-1-ol | | IUPACName = Octan-1-ol | ||
| | OtherNames = |
| OtherNames = 1-Octanol; Capryl alcohol; Octyl alcohol | ||
| | Section1 = {{Chembox Identifiers | | Section1 = {{Chembox Identifiers | ||
| | CASNo_Ref = {{cascite}} | | CASNo_Ref = {{cascite|correct|CAS}} | ||
| | CASNo = 111-87-5 | | CASNo = 111-87-5 | ||
| | SMILES = CCCCCCCCO | | SMILES = CCCCCCCCO | ||
| Line 16: | Line 16: | ||
| }} | }} | ||
| | Section2 = {{Chembox Properties | | Section2 = {{Chembox Properties | ||
| | |
| C=8|H=18|O=1 | ||
| | MolarMass = 130.23 g/mol | |||
| | Density = 0.824 g/cm<sup>3</sup> | | Density = 0.824 g/cm<sup>3</sup> | ||
| | Solubility = Insoluble | | Solubility = Insoluble | ||
| Line 27: | Line 26: | ||
| '''Octanol''' is a straight chain ] with eight ] ]s and the molecular formula CH<sub>3</sub>(CH<sub>2</sub>)<sub>7</sub>OH. Although the term ''octanol'' usually refers exclusively to the ] 1-octanol, there are other less common isomers of octanol such as the ]s 2-octanol, 3-octanol and 4-octanol. | '''Octanol''' is a straight chain ] with eight ] ]s and the molecular formula CH<sub>3</sub>(CH<sub>2</sub>)<sub>7</sub>OH. Although the term ''octanol'' usually refers exclusively to the ] 1-octanol, there are other less common isomers of octanol such as the ]s 2-octanol, 3-octanol and 4-octanol. | ||
| Octanol occurs naturally in the form of ]s in some essential oils. The primary use of octanol is in the manufacture of various esters (both synthetic and naturally occurring), such as ], 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.<ref> Bushara K. |
Octanol occurs naturally in the form of ]s in some essential oils. The primary use of octanol is in the manufacture of various esters (both synthetic and naturally occurring), such as ], 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.<ref>{{cite journal | author = Bushara K. et al. | title = Pilot trial of 1-octanol in essential tremor | journal = Neurology | year = 2004 | volume = 62 | pages = 122-124}}</ref> | ||
| ==Preparation== | ==Preparation== | ||
| Octanol is produced industrially by the oligomerization of ] using ] followed by oxidation of the ].<ref name=Falbe>Jürgen Falbe, Helmut Bahrmann, Wolfgang Lipps, Dieter Mayer "Alcohols, Aliphatic" in Ullmann's Encyclopedia of Chemical Technology Wiley-VCH Verlag; Weinheim, 2002. |
Octanol is produced industrially by the oligomerization of ] using ] followed by oxidation of the ].<ref name=Falbe>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}}</ref> An idealized synthesis is shown: | ||
| :Al(C<sub>2</sub>H<sub>5</sub>)<sub>3</sub> + 9 C<sub>2</sub>H<sub>4</sub> → Al(C<sub>8</sub>H<sub>17</sub>)<sub>3</sub> | :Al(C<sub>2</sub>H<sub>5</sub>)<sub>3</sub> + 9 C<sub>2</sub>H<sub>4</sub> → Al(C<sub>8</sub>H<sub>17</sub>)<sub>3</sub> | ||
| :Al(C<sub>8</sub>H<sub>17</sub>)<sub>3</sub> + 3 O + 3 H<sub>2</sub>O → 3 HOC<sub>8</sub>H<sub>17</sub> + Al(OH)<sub>3</sub> | :Al(C<sub>8</sub>H<sub>17</sub>)<sub>3</sub> + 3 O + 3 H<sub>2</sub>O → 3 HOC<sub>8</sub>H<sub>17</sub> + Al(OH)<sub>3</sub> | ||
| Line 37: | Line 36: | ||
| ==Water/octanol partitioning== | ==Water/octanol partitioning== | ||
| {{see also|Partition coefficient}} | {{see also|Partition coefficient}} | ||
| Octanol and ] are ]. The distribution of a compound between water and octanol is used to calculate the ] '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 ] and ] ]s of living systems. |
Octanol and ] are ]. The distribution of a compound between water and octanol is used to calculate the ] '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 ] and ] ]s of living systems.<ref>{{Cite book | ||
| | last1 = Schwarzenbach | first1 = Rene P. | | last1 = Schwarzenbach | first1 = Rene P. | ||
| | last2 = Gschwend | first2 = Philip M. | | last2 = Gschwend | first2 = Philip M. | ||
| Line 47: | Line 46: | ||
| </ref> | </ref> | ||
| Many dermal absorption models consider the ]/ water partition coefficient to be well approximated by a function of the water/ octanol partition coefficient of the form |
Many dermal absorption models consider the ]/ water partition coefficient to be well approximated by a function of the water/ octanol partition coefficient of the form:<ref>{{cite journal | ||
| | author = McCarley KD, Bunge AL | | author = McCarley KD, Bunge AL | ||
| | title = Pharmacokinetic Models of Dermal Absorption | | title = Pharmacokinetic Models of Dermal Absorption | ||
| Line 57: | Line 56: | ||
| | pmid = 11745728 | | pmid = 11745728 | ||
| | doi = 10.1002/jps.1120 | | doi = 10.1002/jps.1120 | ||
| }}</ref> |
}}</ref> | ||
| :<math>\log(K_{sc/w}) = a + b\log(K_{w/o})</math> | :<math>\log(K_{sc/w}) = a + b\log(K_{w/o})</math> | ||
| Where a and b are constants,<math>K_{sc/w}</math> is the stratum corneum/ water partition coefficient, and<math>K_{w/o}</math> is the water/ octanol partition coefficient. The values of a and b vary between papers, but Cleek & Bunge |
Where a and b are constants,<math>K_{sc/w}</math> is the stratum corneum/ water partition coefficient, and<math>K_{w/o}</math> is the water/ octanol partition coefficient. The values of a and b vary between papers, but Cleek & Bunge<ref>{{cite journal | ||
| | author = Cleek RL, Bunge AL | | author = Cleek RL, Bunge AL | ||
| | title = A new method for estimating dermal absorption from chemical exposure. 1. General approach | | title = A new method for estimating dermal absorption from chemical exposure. 1. General approach | ||
| Line 71: | Line 70: | ||
| | pmid = 8483831 | | pmid = 8483831 | ||
| | doi = 10.1023/A:1018981515480 | | doi = 10.1023/A:1018981515480 | ||
| ⚫ | }}</ref> have reported the values a=0, b=0.74. | ||
| }}</ref> | |||
| ⚫ | have reported the values a=0, b=0.74. | ||
| ==References== | ==References== | ||
| {{reflist}} | |||
| <references /> | |||
| {{Alcohols}} | {{Alcohols}} | ||
Revision as of 18:36, 17 March 2011
| |
| |
| Names | |
|---|---|
| IUPAC name Octan-1-ol | |
| Other names 1-Octanol; Capryl alcohol; Octyl alcohol | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| PubChem CID | |
SMILES
| |
| Properties | |
| Chemical formula | C8H18O |
| Molar mass | 130.231 g·mol |
| Density | 0.824 g/cm |
| Melting point | −16 °C (3 °F; 257 K) |
| Boiling point | 195 °C (383 °F; 468 K) |
| Solubility in water | Insoluble |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
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.
Preparation
Octanol is produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products. 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
See also: Partition coefficientOctanol 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.
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:
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 have reported the values a=0, b=0.74.
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 have reported the values a=0, b=0.74.
References
- Bushara K.; et al. (2004). "Pilot trial of 1-octanol in essential tremor". Neurology. 62: 122–124.
{{cite journal}}: Explicit use of et al. in:|author=(help) - 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
- Schwarzenbach, Rene P.; Gschwend, Philip M.; Imboden, Dieter M. (2003). Environmental organic chemistry. John Wiley. ISBN 0471350532.
- 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.
