Eicosane

Eicosane

Names
Preferred IUPAC name Icosane [1]
Other names n-Eicosane, Eichosane
Identifiers
CAS Number	112-95-8  Y
3D model (JSmol)	Interactive image
Beilstein Reference	1700722
ChEBI	CHEBI:43619  Y
ChEMBL	ChEMBL1233983  N
ChemSpider	7929  Y
ECHA InfoCard	100.003.653
EC Number	204-018-1
MeSH	eicosane
PubChem CID	8222
UNII	3AYA9KEC48  Y
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/h3-20H2,1-2H3 Y Key: CBFCDTFDPHXCNY-UHFFFAOYSA-N Y
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)	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). N  verify  (what is  YN ?) Infobox references

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

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. ^[3]

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. ^[4]

Naming

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

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.

External links

• Icosane at Dr. Duke's Phytochemical and Ethnobotanical Databases