Hexadecane
Hexadecane
Chemical compound
Hexadecane (also called cetane) is an alkane hydrocarbon with the chemical formula C16H34. Hexadecane consists of a chain of 16 carbon atoms, with three hydrogen atoms bonded to the two end carbon atoms, and two hydrogens bonded to each of the 14 other carbon atoms.
| Names | |
|---|---|
| Preferred IUPAC name
Hexadecane[1] | |
| Other names
Cetane | |
| Identifiers | |
| |
3D model (JSmol) |
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| 1736592 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
|
| ECHA InfoCard | 100.008.072  |
| EC Number |
|
| 103739 | |
| MeSH | n-hexadecane |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C16H34 | |
| Molar mass | 226.448 g·mol−1 |
| Appearance | Colourless liquid |
| Odor | Gasoline-like to odorless |
| Density | 0.77 g/cm3[2][3] |
| Melting point | 18.18 °C (64.72 °F; 291.33 K)[2] |
| Boiling point | 286.9 °C (548.4 °F; 560.0 K)[2] |
| log P | 8.859 |
| Vapor pressure | < 0.1 mbar (20 °C) |
Henry's law constant (kH) |
43 nmol Pa−1 kg−1 |
| -187.6·10−6 cm3/mol[4] | |
| Thermal conductivity | 0.140 W/(m·K)[5] |
Refractive index (nD) |
1.4329[2] |
| Viscosity | 3.03 mPa·s[6] |
| Thermochemistry[7] | |
Heat capacity (C) |
501.6 J K−1 mol−1 |
Std enthalpy of formation (ΔfH⦵298) |
−456.1 kJ mol−1 |
| Hazards | |
| GHS labelling: | |
 | |
| Warning | |
| H315 | |
| Flash point | 136 °C (277 °F; 409 K)[8] |
| 202 °C (396 °F; 475 K)[8] | |
| Related compounds | |
Related alkanes |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cetane is often used as a shorthand for cetane number, a measure of the combustion of diesel fuel.[9] Cetane ignites very easily under compression; for this reason, it is assigned a cetane number of 100, and serves as a reference for other fuel mixtures.[10]
Hexadecyl is an alkyl radical of carbon and hydrogen derived from hexadecane, with formula C16H33 and with mass 225.433,[11] occurring especially in cetyl alcohol.[12] It confers strong hydrophobicity on molecules containing it.[13] Carboplatin modified with hexadecyl and polyethylene glycol has increased liposolubility and PEGylation, proposed to useful in chemotherapy, specifically non-small-cell lung cancer.[14]
Hexadecyl was used from 1982 for radiolabelling,[15] and this continues to be useful,[16] for example for radiolabelling exosomes and hydrogels,[17] and for positron emission tomography.[18]
Hexadecyl platelet-activating factor has profound effects on the lung,[19] and hexadecyl glyceryl ether participates in the biosynthesis of plasmalogens.[20]
- Haynes, p. 3.294
- Haynes, p. 3.578
- Haynes, p. 6.256
- Haynes, p. 6.245
- Haynes, p. 5.21
- Haynes, p. 16.25
- Speight, James G. (2015). Handbook of Petroleum Product Analysis. Hoboken, NJ: Wiley. pp. 158–159. ISBN 978-1-322-95015-0. OCLC 903318141.
- "Hexadecyl". Royal Society of Chemistry. ChemSpider. Retrieved 3 April 2021.
- "hexadecyl noun". Merriam-Webster.
- Hatanaka, K (2011). Horváth, István T. (ed.). Fluorous Chemistry. Springer Science & Business Media. p. 294. ISBN 9783642252334.
- Lang, Tingting; Li, Nuannuan; Zhang, Jing; Li, Yi; Rong, Rong; Fu, Yuanlei (2021). "Prodrug-based nano-delivery strategy to improve the antitumor ability of carboplatin in vivo and in vitro". Drug Delivery. 28 (1): 1272–1280. doi:10.1080/10717544.2021.1938754. PMC 8238065. PMID 34176381.
- Manual Kollareth, Denny Joseph; Chang, Chuchun L.; Hansen, Inge H.; Deckelbaum, Richard J. (2018). "Radiolabeled cholesteryl ethers: A need to analyze for biological stability before use". Biochemistry and Biophysics Reports. 13: 1–6. doi:10.1016/j.bbrep.2017.10.007. PMC 5697731. PMID 29188234.
- Lee, Yanick (July 2017). Radiosynthesis of hexadecyl-4-[ 18F]fluorobenzoate for labeling exosomes and chitosan hydrogels (Master's thesis). Université de Montréal.
- "Radioactive cell labeling agent". KR101130737B1. 2012.
- Haroldsen, P. E.; Voelkel, N. F.; Henson, J. E.; Henson, P. M.; Murphy, R. C. (1987). "Metabolism of platelet-activating factor in isolated perfused rat lung". Journal of Clinical Investigation. 79 (6): 1860–1867. doi:10.1172/JCI113028. PMC 424530. PMID 3108322.
- Wood, Randall; Healy, Kathleen (1970). "Tumor lipids: Biosynthesis of plasmalogens". Biochemical and Biophysical Research Communications. 38 (2): 205–211. doi:10.1016/0006-291x(70)90697-2. PMID 5418699.
- Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. ISBN 9781498754293.
- Vapor pressure and liquid density calculation
- Technique to determine hexadecane transfer