Icosane: Difference between revisions

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	{{~~chembox~~		{{Chembox
			\| Verifiedfields = changed
	\| verifiedrevid = 396495006
			\| Watchedfields = changed
	\| References=<ref></ref>
			\| verifiedrevid = 443869216
	\| ImageFile_Ref = {{chemboximage\|correct\|??}}
	\| ImageFile = Eicosane.png		\| ImageFile = Eicosane.png
			\| ImageFile_Ref = {{chemboximage\|correct\|??}}
	\| ImageSize = 290px
			\| ImageSize = 300
	\| ImageName = Skeletal formula of icosane
			\| ImageAlt = Structural formula of icosane
	\| ImageFile1 = Icosane-3D-balls.png
			\| ImageFile1 = Icosane 3D ball.png
	\| ImageSize1 = 300px
			\| ImageFile1_Ref = {{chemboximage\|correct\|??}}
	\| ImageName1 = Ball-and-stick model of icosane
			\| ImageSize1 = 300
	\| IUPACName=Icosane
			\| ImageAlt1 = Ball and stick model of the icosane molecule
	\| OtherNames=Didecyl<br>''n''-Eicosane
			\| PIN = Icosane<ref>{{cite book \|author=] \|date=2014 \|title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 \|publisher=] \|pages=59 \|doi=10.1039/9781849733069 \|isbn=978-0-85404-182-4}}</ref>
	\| Section1={{Chembox Identifiers
			\| OtherNames = Eicosane
	\| InChIKey = CBFCDTFDPHXCNY-UHFFFAOYAJ
			\|Section1={{Chembox Identifiers
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
			\| CASNo = 112-95-8
	\| StdInChI = 1S/C20H42/c1-3-5-7-9-11-13-15-17-19-20-18-16-14-12-10-8-6-4-2/h3-20H2,1-2H3
	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = CBFCDTFDPHXCNY-UHFFFAOYSA-N
	\| CASNo_Ref = {{cascite\|correct\|CAS}}		\| CASNo_Ref = {{cascite\|correct\|CAS}}
			\| PubChem = 8222
	\| CASNo=112-95-8
			\| ChemSpiderID = 7929
	\| PubChem=8222
			\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| EINECS=204-018-1
	\| UNII = 3AYA9KEC48		\| UNII = 3AYA9KEC48
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| EINECS = 204-018-1
			\| MeSHName = eicosane
	\| ChEBI = 43619		\| ChEBI = 43619
			\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| SMILES = C(CCCCCCCCCCCCCCCCC)CC
			\| ChEMBL = 1233983
	\| InChI=1/C20H42/c1-3-5-7-9-11-13-15-17-19-20-18-16-14-12-10-8-6-4-2/h3-20H2,1-2H3
			\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
			\| Beilstein = 1700722
	\| ChemSpiderID=7929
			\| SMILES = CCCCCCCCCCCCCCCCCCCC
	}}
			\| StdInChI = 1S/C20H42/c1-3-5-7-9-11-13-15-17-19-20-18-16-14-12-10-8-6-4-2/h3-20H2,1-2H3
	\| Section2={{Chembox Properties
			\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| Formula=C<sub>20</sub>H<sub>42</sub>
			\| StdInChIKey = CBFCDTFDPHXCNY-UHFFFAOYSA-N
	\| MolarMass=282.5475 g/mol
			\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| Appearance=Colorless crystals or wax-like solid
			}}
	\| Density=
			\|Section2={{Chembox Properties
	\| MeltingPtC=36.7
			\| C=20 \| H=42
	\| BoilingPtC=342.7
			\| Appearance = Colorless, waxy crystals
	\| Solubility=Insoluble
			\| Odor = Odorless
	}}
			\| MeltingPtK = 309 to 311
	\| Section3={{Chembox Hazards
			\| BoilingPtK = 616.2
	\| MainHazards=
			\| LogP = 10.897
	\| FlashPt=
			\| HenryConstant = 31 μmol Pa<sup>−1</sup> kg<sup>−1</sup>
	\| Autoignition=
	}}		}}
			\|Section3={{Chembox Thermochemistry
			\| Entropy = 558.6 J K<sup>−1</sup> mol<sup>−1</sup>
			\| HeatCapacity = 602.5 J K<sup>−1</sup> mol<sup>−1</sup> (at 6.0 °C)
			}}
			\|Section4={{Chembox Hazards
			\| FlashPt = >
			\| FlashPtC = 113
			\| NFPA-F = 1
			\| NFPA-H = 0
			\| NFPA-R = 0
			}}
			\|Section5={{Chembox Related
			\| OtherFunction_label = alkanes
			\| OtherFunction = {{Unbulleted list\|]\|]}}
			}}
	}}		}}
			'''Icosane''' (alternative spelling '''eicosane''') is an ] with the ] C<sub>20</sub>H<sub>42</sub>. It has 366,319 ]s.

			Icosane has little use in the ], as its high ] makes it an inefficient fuel. ''n''-Icosane (the straight-chain structural ] of icosane) is the shortest compound found in ]es used to form candles.
	'''Icosane''' (also known by the name '''eicosane''' or as '''didecyl''') is an ] with the ] C<sub>20</sub>H<sub>42</sub>. It has 366,319 ]s.

			Icosane's size, state or chemical inactivity does not exclude it from the traits its smaller alkane counterparts have. It is a colorless, non-polar ], nearly unreactive except when it burns. It is less dense than and insoluble in water. Its non-polar trait means it can only perform weak ] bonding (]/]s).
	Icosane has little use in the ] industry, as its high ] makes it an inefficient fuel. Due to its chemical inactivity, ''n''-icosane (the straight-chain structural ] of icosane) is part of the ] group, and is the shortest molecule in the ] used to form candles.

	Icosane's size, state or chemical inactivity does not exclude it from the traits its smaller alkane counterparts have. It is a colorless, less dense than water, non-polar ], nearly non-reactive unless combusted, and insoluble in water. Its non-polar trait means it can only perform weak ] bonding (]/]s).

	Icosane's phase transition at a moderate temperature makes it a candidate ], or PCM which can be used to store thermal energy and control temperature.		Icosane's phase transition at a moderate temperature makes it a candidate ], or PCM which can be used to store thermal energy and control temperature.

			It can be detected in the body odor of persons suffering from ].<ref>{{cite journal \|last1= Trivedi\|first1= Drupad K.\|last2= Sinclair\|first2= Eleanor\|last3= Xu\|first3= Yun\|last4= Sarkar\|first4= Depanjan\|last5= Walton-Doyle\|first5= Caitlin\|last6= Liscio\|first6= Camilla\|last7= Banks\|first7= Phine\|last8= Milne\|first8= Joy\|last9= Silverdale\|first9= Monty\|last10= Kunath\|first10= Tilo\|last11= Goodacre\|first11= Royston\|last12= Barran\|first12= Perdita\|title= Discovery of Volatile Biomarkers of Parkinson's Disease from Sebum\|journal= ACS Central Science\|year= 2019\|volume= 5\|issue= 4\|pages= 599–606\|doi=10.1021/acscentsci.8b00879 \|pmid= 31041379\|pmc= 6487537}}</ref>

	==Naming==		==Naming==
	IUPAC currently recommends '''icosane''',<ref name=IUPAC1>{{cite web\|url=http://www.acdlabs.com/iupac/nomenclature/93/r93_328.htm\|title=Table 11 Basic numerical terms (multiplying affixes)\|publisher=]\|~~accessdate~~=2011-02-16}}</ref> whereas ] and ] use '''eicosane'''.<ref name=IUPAC2>{{cite web\|url=http://www.acdlabs.com/iupac/nomenclature/93/r93_332.htm\|title=Footnote for Table 11\|publisher=]\|~~accessdate~~=2011-02-16}}</ref>		IUPAC currently recommends '''icosane''',<ref name=IUPAC1>{{cite web\|url=http://www.acdlabs.com/iupac/nomenclature/93/r93_328.htm\|title=Table 11 Basic numerical terms (multiplying affixes)\|publisher=]\|access-date=2011-02-16}}</ref> whereas ] and ] use '''eicosane'''.<ref name=IUPAC2>{{cite web\|url=http://www.acdlabs.com/iupac/nomenclature/93/r93_332.htm\|title=Footnote for Table 11\|publisher=]\|access-date=2011-02-16}}</ref>

			== See also ==

			* ]

	==References==		==References==
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	==External links==		==External links==
	* at Dr. Duke's Phytochemical and Ethnobotanical Databases		* at Dr. Duke's Phytochemical and Ethnobotanical Databases
			{{Alkanes}}

	{{alkanes}}

	]		]

	]
	]
	]
	]
	]
	]
	]
	]
	]

Latest revision as of 20:53, 18 March 2023

Icosane
Names


Preferred IUPAC name Icosane
Other names Eicosane
Identifiers
CAS Number	112-95-8
3D model (JSmol)	Interactive image
Beilstein Reference	1700722
ChEBI	CHEBI:43619
ChEMBL	ChEMBL1233983
ChemSpider	7929
ECHA InfoCard	100.003.653
EC Number	204-018-1
MeSH	eicosane
PubChem CID	8222
UNII	3AYA9KEC48
CompTox Dashboard (EPA)	DTXSID1025227
InChI InChI=1S/C20H42/c1-3-5-7-9-11-13-15-17-19-20-18-16-14-12-10-8-6-4-2/h3-20H2,1-2H3Key: CBFCDTFDPHXCNY-UHFFFAOYSA-N
SMILES CCCCCCCCCCCCCCCCCCCC
Properties
Chemical formula	C₂₀H₄₂
Molar mass	282.556 g·mol
Appearance	Colorless, waxy crystals
Odor	Odorless
Melting point	36 to 38 °C; 97 to 100 °F; 309 to 311 K
Boiling point	343.1 °C; 649.5 °F; 616.2 K
log P	10.897
Henry's law constant (k_H)	31 μmol Pa kg
Thermochemistry
Heat capacity (C)	602.5 J K mol (at 6.0 °C)
Std molar entropy (S₂₉₈)	558.6 J K mol
Hazards
NFPA 704 (fire diamond)	0 1 0
Flash point	> 113 °C (235 °F; 386 K)
Related compounds
Related alkanes	Nonadecane Heneicosane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Icosane (alternative spelling eicosane) is an alkane with the chemical formula C₂₀H₄₂. It has 366,319 constitutional isomers.

Icosane has little use in the petrochemical industry, as its high flash point makes it an inefficient fuel. n-Icosane (the straight-chain structural isomer of icosane) is the shortest compound found in paraffin waxes used to form candles.

Icosane's size, state or chemical inactivity does not exclude it from the traits its smaller alkane counterparts have. It is a colorless, non-polar molecule, nearly unreactive except when it burns. It is less dense than and insoluble in water. Its non-polar trait means it can only perform weak intermolecular bonding (hydrophobic/van der Waals forces).

Icosane's phase transition at a moderate temperature makes it a candidate phase change material, or PCM which can be used to store thermal energy and control temperature.

It can be detected in the body odor of persons suffering from Parkinson's disease.

Naming

IUPAC currently recommends icosane, whereas Chemical Abstracts Service and Beilstein use eicosane.

References

International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 59. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
Trivedi, Drupad K.; Sinclair, Eleanor; Xu, Yun; Sarkar, Depanjan; Walton-Doyle, Caitlin; Liscio, Camilla; Banks, Phine; Milne, Joy; Silverdale, Monty; Kunath, Tilo; Goodacre, Royston; Barran, Perdita (2019). "Discovery of Volatile Biomarkers of Parkinson's Disease from Sebum". ACS Central Science. 5 (4): 599–606. doi:10.1021/acscentsci.8b00879. PMC 6487537. PMID 31041379.
"Table 11 Basic numerical terms (multiplying affixes)". IUPAC. Retrieved 2011-02-16.
"Footnote for Table 11". IUPAC. Retrieved 2011-02-16.

External links

Icosane at Dr. Duke's Phytochemical and Ethnobotanical Databases

v t e Alkanes
Methane (CH₄) Ethane (C₂H₆) Propane (C₃H₈) Butane (C₄H₁₀) Pentane (C₅H₁₂) Hexane (C₆H₁₄) Heptane (C₇H₁₆) Octane (C₈H₁₈) Nonane (C₉H₂₀) Decane (C₁₀H₂₂) Undecane (C₁₁H₂₄) Dodecane (C₁₂H₂₆) Tridecane (C₁₃H₂₈) Tetradecane (C₁₄H₃₀) Pentadecane (C₁₅H₃₂) Hexadecane / Cetane (C₁₆H₃₄) Heptadecane (C₁₇H₃₆) Octadecane (C₁₈H₃₈) Nonadecane (C₁₉H₄₀) Icosane (C₂₀H₄₂) Heneicosane (C₂₁H₄₄) Tetracosane (C₂₄H₅₀) Nonacosane (C₂₉H₆₀) Hentriacontane (C₃₁H₆₄)
Higher alkanes List of alkanes

Alkanes

Methane (CH₄)
Ethane (C₂H₆)
Propane (C₃H₈)
Butane (C₄H₁₀)
Pentane (C₅H₁₂)
Hexane (C₆H₁₄)
Heptane (C₇H₁₆)
Octane (C₈H₁₈)
Nonane (C₉H₂₀)
Decane (C₁₀H₂₂)
Undecane (C₁₁H₂₄)
Dodecane (C₁₂H₂₆)
Tridecane (C₁₃H₂₈)
Tetradecane (C₁₄H₃₀)
Pentadecane (C₁₅H₃₂)
Hexadecane / Cetane (C₁₆H₃₄)
Heptadecane (C₁₇H₃₆)
Octadecane (C₁₈H₃₈)
Nonadecane (C₁₉H₄₀)
Icosane (C₂₀H₄₂)
Heneicosane (C₂₁H₄₄)
Tetracosane (C₂₄H₅₀)
Nonacosane (C₂₉H₆₀)
Hentriacontane (C₃₁H₆₄)

Category:

Alkanes

Latest revision as of 20:53, 18 March 2023

Naming

See also

References

External links