1-Decanol: Difference between revisions

1-Decanol^[1]
Names
	Preferred IUPAC name Decan-1-ol
	Other names decyl alcohol; n-decyl alcohol; capric alcohol; epal 10; antak; agent 504
Identifiers
CAS Number	112-30-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28903 ;
ChEMBL	ChEMBL25363 ;
ChemSpider	7882 ;
ECHA InfoCard	100.003.597
KEGG	C01633 ;
PubChem CID	8174;
UNII	89V4LX791F ;
CompTox Dashboard (EPA)	DTXSID7021946 ;
	InChI InChI=1S/C10H21OH/c1-2-3-4-5-6-7-8-9-10-11/h11H,2-10H2,1H3 Key: MWKFXSUHUHTGQN-UHFFFAOYSA-N ; InChI=1/C10H21OH/c1-2-3-4-5-6-7-8-9-10-11/h11H,2-10H2,1H3 Key: MWKFXSUHUHTGQN-UHFFFAOYAN;
	SMILES OCCCCCCCCCC;
Properties
Chemical formula	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)
Solubility in water	37 mg/L at 20°C
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). verify (what is ?) Infobox references

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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

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

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

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

References

^ Merck Index, 12th Edition, 2911.
^ "1-Decanol".
^ "Material Safety Data Sheet - Decyl alcohol, 99%". fscimage.fishersci.com. Archived from the original on 2021-09-01. Retrieved 2021-09-01.
^ 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.
^ 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.

[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.

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[2]

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[5]

@@ Line 1: / Line 1: @@
 {{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)
-|   Interfacial tension = 8.97 mN/m (against water @ 20 °C)
-|   MeltingPtC = 6.4
-|   BoilingPtC = 232.9
-|   Appearance = Viscous liquid
-|   Solubility = Insoluble
-  }}
-| Section7 = {{Chembox Hazards
-|   FlashPt = 108 °C
-|   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>
+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==
+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==
+{{Reflist}}
-<references/>
 {{Alcohols}}
@@ Line 65: / Line 69: @@
 [[Category:Fatty alcohols]]
 [[Category:Primary alcohols]]
+[[Category:Alkanols]]
+[[Category:Decyl compounds]]