Icosane

Icosane
Structural formula of icosane
Ball and stick model of the icosane molecule
Names
Preferred IUPAC name
Icosane[1]
Other names
Eicosane, Eichosane
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference
 1700722
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.653
EC Number
  • 204-018-1
MeSH eicosane
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C20H42/c1-3-5-7-9-11-13-15-17-19-20-18-16-14-12-10-8-6-4-2/h3-20H2,1-2H3 checkY
    Key: CBFCDTFDPHXCNY-UHFFFAOYSA-N checkY
SMILES
  • CCCCCCCCCCCCCCCCCCCC
Properties
Chemical formula
 C20H42
Molar mass 282.556 g·mol−1
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 (kH)
 31 μmol Pa−1 kg−1
Thermochemistry
Heat capacity (C)
 602.5 J K−1 mol−1 (at 6.0 °C)
Std molar
entropy (S⦵298)
 558.6 J K−1 mol−1
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored 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 [77 °F], 100 kPa).
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Infobox references

Icosane (alternative spelling eicosane and eichosane[2]) is an alkane with the chemical formula C20H42. It has 366,319 constitutional isomers.

n-Icosane (the straight-chain structural isomer of icosane) is the shortest compound found in paraffin waxes used to form candles. It can be isolated from Agave attenuate leaves. It is also found in Vanilla madagascariensis and Gymnodinium nagasakiense.[3]

Icosane's size, state or chemical inactivity does not exclude it from the traits its smaller alkane counterparts have. 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 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.[4]

Naming

IUPAC currently recommends icosane,[5] whereas Chemical Abstracts Service and Beilstein use eicosane.[6]

See also

  • Perillaldehyde

References

  1. ↑ 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.
  2. ↑ Vargaftik, N. B. (1983). Handbook of physical properties of liquids and gases: pure substances and mixtures (2nd ed.). Washington: Hemisphere Pub. Corp. ISBN 9780891163565.
  3. ↑ Eicosane Pubchem
  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.
  5. ↑ "Table 11 Basic numerical terms (multiplying affixes)". IUPAC. Retrieved 2011-02-16.
  6. ↑ "Footnote for Table 11". IUPAC. Retrieved 2011-02-16.
  • Icosane at Dr. Duke's Phytochemical and Ethnobotanical Databases
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