View source for Eicosane

{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 443869216
| ImageFile = Eicosane.png
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 300
| ImageAlt = Structural formula of icosane
| ImageFile1 = Icosane 3D ball.png
| ImageFile1_Ref = {{chemboximage|correct|??}}
| ImageSize1 = 300
| ImageAlt1 = Ball and stick model of the icosane molecule
| PIN = Icosane<ref>{{cite book |author=[[International Union of Pure and Applied Chemistry]] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=[[Royal Society of Chemistry|The Royal Society of Chemistry]] |pages=59 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>
| OtherNames = ''n''-Eicosane, Eichosane
|Section1={{Chembox Identifiers
| CASNo = 112-95-8
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 8222
| ChemSpiderID = 7929 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII = 3AYA9KEC48
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 204-018-1
| MeSHName = eicosane
| ChEBI = 43619
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1233983
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| Beilstein = 1700722
| 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CBFCDTFDPHXCNY-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
| C=20 | H=42 
| Appearance = Colorless, waxy crystals
| Odor = Odorless
| MeltingPtK = 309 to 311 
| BoilingPtK = 616.2
| LogP = 10.897
| HenryConstant = 31 μmol Pa<sup>−1</sup> kg<sup>−1</sup>
}}
|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&nbsp;°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|[[Nonadecane]]|[[Heneicosane]]}}
}}
}}
'''Eicosane''' (alternative spellings '''icosane''' and '''eichosane'''<ref>{{cite book |last1=Vargaftik |first1=N. B. |title=Handbook of physical properties of liquids and gases: pure substances and mixtures |date=1983 |publisher=Hemisphere Pub. Corp |location=Washington |isbn=9780891163565 |edition=2nd}}</ref>) is an [[alkane]] with the [[chemical formula]] C<sub>20</sub>H<sub>42</sub>. It has 366,319 [[constitutional isomer]]s.<ref>{{Cite web
 | last       = NMPPDB
 | title      = "NMPC‑1133 (Humulene epoxide) – Nigerian Medicinal Plants & Phytochemicals Database"
 | url        = https://nmppdb.com.ng/compounds-detail?compound=1133
 | publisher  = NMPPDB
 | access-date= 2025-06-24}}</ref>

''n''-Eicosane (the straight-chain structural [[isomer]] of eicosane) is the shortest compound found in [[paraffin wax]]es, used to form candles. It can be isolated from [[agave attenuata|agave attenuate]] leaves. It is also found in Vanilla madagascariensis and Gymnodinium nagasakiense.<ref name="Pubchem">[https://pubchem.ncbi.nlm.nih.gov/compound/Eicosane Eicosane Pubchem]</ref>

Eicosane's size, state and chemical inactivity do not exclude it from the traits of its smaller alkane counterparts. It is a colorless or white, 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 force]]s).

Eicosane'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]].<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==
It is derived from ἐίκοσι (''eikosi''), Greek for 20 (cf. ''icosahedron'').

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=[[IUPAC]]|access-date=2011-02-16}}</ref> whereas [[Chemical Abstracts Service]] and [[Beilstein database|Beilstein]] use '''eicosane'''.<ref name=IUPAC2>{{cite web|url=http://www.acdlabs.com/iupac/nomenclature/93/r93_332.htm|title=Footnote for Table 11|publisher=[[IUPAC]]|access-date=2011-02-16}}</ref>

== See also ==

* [[Perillaldehyde]]

==References==
{{Reflist}}

==External links==
* [https://web.archive.org/web/20150923173912/http://www.ars-grin.gov/cgi-bin/duke/chemical.pl?EICOSANE Icosane] at Dr. Duke's Phytochemical and Ethnobotanical Databases
{{Alkanes}}

[[Category:Alkanes]]