Jump to content

1-Decanol: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous edit
Content deleted Content added
VisualWikitext
format temperatures Flashpoint, Autoignition, replaced: FlashPt → FlashPtC using AWB
 
(31 intermediate revisions by 23 users not shown)
Line 1: Line 1:
{{chembox
{{chembox
|Watchedfields = changed
| verifiedrevid = 477207517
|verifiedrevid = 477207517
| Reference = <ref>''[[Merck Index]]'', 12th Edition, '''2911'''.</ref>
|Reference = <ref>''[[Merck Index]]'', 12th Edition, '''2911'''.</ref>
| Name = 1-Decanol
| ImageFile = 1-Decanol.png
|Name = 1-Decanol
|ImageFile = 1-Decanol.png
| ImageSize = 220px
|ImageSize = 220px
| ImageName = Skeletal formula
|ImageName = Skeletal formula
| ImageFile1 = 1-Decanol-3D-vdW.png
|ImageFile1 = 1-Decanol-3D-vdW.png
| ImageName1 = Space-filling model
|ImageName1 = Space-filling model
| IUPACName = Decan-1-ol
|PIN = Decan-1-ol
| OtherNames = decyl alcohol<br />''n''-decyl alcohol<br />capric alcohol<br />epal 10<br />antak<br />agent 504
|OtherNames = decyl alcohol<br />''n''-decyl alcohol<br />capric alcohol<br />epal 10<br />antak<br />agent 504
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28903
|ChEBI = 28903
| ChemSpiderID = 7882
|ChemSpiderID = 7882
| UNII_Ref = {{fdacite|correct|FDA}}
|UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 89V4LX791F
|UNII = 89V4LX791F
| KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C01633
|KEGG = C01633
| InChI = 1/C10H22O/c1-2-3-4-5-6-7-8-9-10-11/h11H,2-10H2,1H3
|InChI = 1/C10H21OH/c1-2-3-4-5-6-7-8-9-10-11/h11H,2-10H2,1H3
| InChIKey = MWKFXSUHUHTGQN-UHFFFAOYAN
|InChIKey = MWKFXSUHUHTGQN-UHFFFAOYAN
| ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 25363
|ChEMBL = 25363
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H22O/c1-2-3-4-5-6-7-8-9-10-11/h11H,2-10H2,1H3
|StdInChI = 1S/C10H21OH/c1-2-3-4-5-6-7-8-9-10-11/h11H,2-10H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MWKFXSUHUHTGQN-UHFFFAOYSA-N
|StdInChIKey = MWKFXSUHUHTGQN-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
|CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 112-30-1
|CASNo = 112-30-1
| SMILES = OCCCCCCCCCC
|SMILES = OCCCCCCCCCC
| PubChem = 8174
|PubChem = 8174
⚫
}}
⚫
| Section2 = {{Chembox Properties
⚫
| Formula = C<sub>10</sub>H<sub>22</sub>O
⚫
| MolarMass = 158.28 g/mol
⚫
| Density = 0.8297 g/cm³
⚫
| Viscosity = 12.048 mPa.s (@ 25 °C)
⚫
| MeltingPtC = 6.4
⚫
| BoilingPtC = 232.9
⚫
| Appearance = Viscous liquid
| Solubility = Insoluble
⚫
}}
⚫
| Section7 = {{Chembox Hazards
⚫
| FlashPtC = 108
⚫
| ExternalMSDS = [http://ptcl.chem.ox.ac.uk/MSDS/DE/decyl_alcohol.html Oxford MSDS]
⚫
}}
}}
}}
⚫
|Section2={{Chembox Properties
⚫
|Formula = C<sub>10</sub>H<sub>21</sub>OH
⚫
|MolarMass = 158.28 g/mol
⚫
|Density = 0.8297 g/cm<sup>3</sup>
⚫
|Viscosity = 12.048 mPa.s (@ 25 °C)
|LogP = 4.57
⚫
|MeltingPtC = 6.4
⚫
|BoilingPtC = 232.9
⚫
|Appearance = Viscous liquid
|Solubility = 37 mg/L at 20°C<ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/1-decanol|title=1-Decanol}}</ref>
⚫
}}
⚫
|Section3={{Chembox Hazards
⚫
|FlashPtC = 108
⚫
|ExternalSDS = [http://ptcl.chem.ox.ac.uk/MSDS/DE/decyl_alcohol.html Oxford MSDS]
⚫
}}
⚫
}}

⚫
'''1-Decanol''' is a straight chain [[fatty alcohol]] with ten [[carbon]] [[atom]]s and the molecular formula C<sub>10</sub>H<sub>21</sub>OH. It is a colorless to light yellow viscous liquid that is insoluble in water and has an aromatic odor.<ref>{{Cite web|title=Material Safety Data Sheet - Decyl alcohol, 99%|url=https://fscimage.fishersci.com/msds/11356.htm|url-status=live|archive-url=https://archive.today/20210901171536/https://fscimage.fishersci.com/msds/11356.htm|archive-date=2021-09-01|access-date=2021-09-01|website=fscimage.fishersci.com}}</ref> The interfacial tension against water at 20 °C is 8.97 mN/m.


==Production==
⚫
'''1-Decanol''' is a straight chain [[fatty alcohol]] with ten [[carbon]] [[atom]]s and the molecular formula C<sub>10</sub>H<sub>21</sub>OH. It is a colorless viscous liquid that is insoluble in water and has a strong odor.<ref>ICSC [http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc14/icsc1490.pdf]</ref> The interfacial tension against water at 20 °C is 8.97 mN/m.
Decanol can be prepared by the [[hydrogenation]] of [[decanoic acid]], which occurs in modest quantities in [[coconut oil]] (about 10%) and [[palm kernel oil]] (about 4%). It may also be produced synthetically via the [[Ziegler process]].


==Uses==
==Uses==
Decanol is used in the manufacture of [[plasticizer]]s, [[lubricant]]s, [[surfactant]]s and solvents. Its ability to permeate the skin has led to it being investigated as a penetration enhancer for [[transdermal]] drug delivery.<ref>{{cite journal|last1=Kanikkannan|first1=N|last2=Singh|first2=Mandip|title=Skin permeation enhancement effect and skin irritation of saturated fatty alcohols|journal=International Journal of Pharmaceutics|date=November 2002|volume=248|issue=1–2|pages=219–228|doi=10.1016/S0378-5173(02)00454-4|pmid=12429475}}</ref><ref>{{cite journal|last1=Williams|first1=Adrian C|last2=Barry|first2=Brian W|title=Penetration enhancers|journal=Advanced Drug Delivery Reviews|date=March 2004|volume=56|issue=5|pages=603–618|doi=10.1016/j.addr.2003.10.025|pmid=15019749}}</ref>
Decanol is used in the manufacture of [[plasticizer]]s, [[lubricant]]s, [[surfactant]]s and solvents.


==Toxicity==
==Safety==
Like other medium chain fatty alcohols, 1-decanol is able to permeate the skin which can lead to irritation.
Decanol causes a high irritability to skin and eyes, when splashed into the eyes it can cause permanent damage. Inhalation and ingestion can be harmful; it can also function as a narcotic. It is harmful in the environment.<ref>MSDS Safety Sheet [http://ptcl.chem.ox.ac.uk/MSDS/DE/decyl_alcohol.html]</ref>


==References==
==References==
{{Reflist}}
<references/>


{{Alcohols}}
{{Alcohols}}
Line 64: Line 69:
[[Category:Fatty alcohols]]
[[Category:Fatty alcohols]]
[[Category:Primary alcohols]]
[[Category:Primary alcohols]]
[[Category:Alkanols]]
[[Category:Decyl compounds]]

Latest revision as of 19:13, 31 March 2024

1-Decanol[1]
Skeletal formula
Space-filling model
Names
Preferred IUPAC name
Decan-1-ol
Other names
decyl alcohol
n-decyl alcohol
capric alcohol
epal 10
antak
agent 504
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.597 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C10H21OH/c1-2-3-4-5-6-7-8-9-10-11/h11H,2-10H2,1H3 checkY
    Key: MWKFXSUHUHTGQN-UHFFFAOYSA-N checkY
  • InChI=1/C10H21OH/c1-2-3-4-5-6-7-8-9-10-11/h11H,2-10H2,1H3
    Key: MWKFXSUHUHTGQN-UHFFFAOYAN
  • OCCCCCCCCCC
Properties
C10H21OH
Molar mass 158.28 g/mol
Appearance Viscous liquid
Density 0.8297 g/cm3
Melting point 6.4 °C (43.5 °F; 279.5 K)
Boiling point 232.9 °C (451.2 °F; 506.0 K)
37 mg/L at 20°C[2]
log P 4.57
Viscosity 12.048 mPa.s (@ 25 °C)
Hazards
Flash point 108 °C (226 °F; 381 K)
Safety data sheet (SDS) Oxford MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

1-Decanol is a straight chain fatty alcohol with ten carbon atoms and the molecular formula C10H21OH. It is a colorless to light yellow viscous liquid that is insoluble in water and has an aromatic odor.[3] The interfacial tension against water at 20 °C is 8.97 mN/m.

Production

[edit]

Decanol can be prepared by the hydrogenation of decanoic acid, which occurs in modest quantities in coconut oil (about 10%) and palm kernel oil (about 4%). It may also be produced synthetically via the Ziegler process.

Uses

[edit]

Decanol is used in the manufacture of plasticizers, lubricants, surfactants and solvents. Its ability to permeate the skin has led to it being investigated as a penetration enhancer for transdermal drug delivery.[4][5]

Safety

[edit]

Like other medium chain fatty alcohols, 1-decanol is able to permeate the skin which can lead to irritation.

References

[edit]
  1. ^ Merck Index, 12th Edition, 2911.
  2. ^ "1-Decanol".
  3. ^ "Material Safety Data Sheet - Decyl alcohol, 99%". fscimage.fishersci.com. Archived from the original on 2021-09-01. Retrieved 2021-09-01.
  4. ^ Kanikkannan, N; Singh, Mandip (November 2002). "Skin permeation enhancement effect and skin irritation of saturated fatty alcohols". International Journal of Pharmaceutics. 248 (1–2): 219–228. doi:10.1016/S0378-5173(02)00454-4. PMID 12429475.
  5. ^ Williams, Adrian C; Barry, Brian W (March 2004). "Penetration enhancers". Advanced Drug Delivery Reviews. 56 (5): 603–618. doi:10.1016/j.addr.2003.10.025. PMID 15019749.
Retrieved from "https://en.wikipedia.org/enwiki/w/index.php?title=1-Decanol&oldid=1216561764"