Eicosane

Eicosane
Structural formula of icosane
Ball and stick model of the icosane molecule
Names
Preferred IUPAC name
Icosane[1]
Other names
n-Eicosane, Eichosane
Identifiers
3D model (JSmol)
1700722
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.653 Edit this at Wikidata
EC Number
  • 204-018-1
MeSH eicosane
UNII
  • 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
  • CCCCCCCCCCCCCCCCCCCC
Properties
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
31 μmol Pa−1 kg−1
Thermochemistry
602.5 J K−1 mol−1 (at 6.0 °C)
558.6 J K−1 mol−1
Hazards
GHS labelling:
GHS08: Health hazard
Danger
H304
P301+P316, P331, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
1
0
Flash point > 113 °C (235 °F; 386 K)
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Eicosane (alternative spellings icosane and eichosane[2]) is an alkane with the chemical formula C20H42. It has 366,319 constitutional isomers.[3]

n-Eicosane (the straight-chain structural isomer of eicosane) 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.[4]

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 forces).

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.[5]

Naming

It is derived from ἐίκοσι (eikosi), Greek for 20 (cf. icosahedron).

IUPAC currently recommends icosane,[6] whereas Chemical Abstracts Service and Beilstein use eicosane.[7]

See also

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. ^ NMPPDB. ""NMPC‑1133 (Humulene epoxide) – Nigerian Medicinal Plants & Phytochemicals Database"". NMPPDB. Retrieved 2025-06-24.
  4. ^ Eicosane Pubchem
  5. ^ 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.
  6. ^ "Table 11 Basic numerical terms (multiplying affixes)". IUPAC. Retrieved 2011-02-16.
  7. ^ "Footnote for Table 11". IUPAC. Retrieved 2011-02-16.
  • Icosane at Dr. Duke's Phytochemical and Ethnobotanical Databases

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