Eicosane
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| Names | |
|---|---|
| Preferred IUPAC name Icosane[1] | |
| Other names n-Eicosane, Eichosane | |
| Identifiers | |
3D model (JSmol) | |
| 1700722 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.003.653 |
| EC Number |
|
| MeSH | eicosane |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
| |
| |
| 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 |
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) | |
| 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). | |
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
[edit]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
[edit]References
[edit]- ^ 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.
- ^ Vargaftik, N. B. (1983). Handbook of physical properties of liquids and gases: pure substances and mixtures (2nd ed.). Washington: Hemisphere Pub. Corp. ISBN 9780891163565.
- ^ NMPPDB. ""NMPC‑1133 (Humulene epoxide) – Nigerian Medicinal Plants & Phytochemicals Database"". NMPPDB. Retrieved 2025-06-24.
- ^ Eicosane Pubchem
- ^ 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
[edit]- Icosane at Dr. Duke's Phytochemical and Ethnobotanical Databases
 | |
 | |
| Names | |
|---|---|
| Preferred IUPAC name Icosane[1] | |
| Other names n-Eicosane, Eichosane | |
| Identifiers | |
| |
3D model (JSmol) |
|
| 1700722 | |
| ChEBI |
|
| ChEMBL |
|
| ChemSpider |
|
| ECHA InfoCard | 100.003.653 |
| EC Number |
|
| MeSH | eicosane |
PubChem CID |
|
| UNII |
|
CompTox Dashboard (EPA) |
|
| |
| |
| 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 |
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) | |
| 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). | |
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
- ^ 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.
- ^ Vargaftik, N. B. (1983). Handbook of physical properties of liquids and gases: pure substances and mixtures (2nd ed.). Washington: Hemisphere Pub. Corp. ISBN 9780891163565.
- ^ NMPPDB. ""NMPC‑1133 (Humulene epoxide) – Nigerian Medicinal Plants & Phytochemicals Database"". NMPPDB. Retrieved 2025-06-24.
- ^ Eicosane Pubchem
- ^ 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