Hexadecane
Structural formula of hexadecane
Ball-and-stick model of the hexadecane molecule
Names
Preferred IUPAC name
Hexadecane[1]
Other names
Cetane
Identifiers
3D model (JSmol)
1736592
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.072 Edit this at Wikidata
EC Number
  • 208-878-9
103739
MeSH n-hexadecane
UNII
  • InChI=1S/C16H34/c1-3-5-7-9-11-13-15-16-14-12-10-8-6-4-2/h3-16H2,1-2H3 checkY
    Key: DCAYPVUWAIABOU-UHFFFAOYSA-N checkY
  • CCCCCCCCCCCCCCCC
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)
43 nmol Pa−1 kg−1
-187.6·10−6 cm3/mol[4]
Thermal conductivity 0.140 W/(m·K)[5]
1.4329[2]
Viscosity 3.03 mPa·s[6]
Thermochemistry[7]
501.6 J K−1 mol−1
−456.1 kJ mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315
Flash point 136 °C (277 °F; 409 K)[8]
202 °C (396 °F; 475 K)[8]
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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.

Cetane number

Main article: Cetane number

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 radical

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]

See also

References

  1. ^ CID 11006 from PubChem
  2. ^ a b c d Haynes, p. 3.294
  3. ^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  4. ^ Haynes, p. 3.578
  5. ^ Haynes, p. 6.256
  6. ^ Haynes, p. 6.245
  7. ^ Haynes, p. 5.21
  8. ^ a b Haynes, p. 16.25
  9. ^ "Cetane". www.mckinseyenergyinsights.com. Archived from the original on 2020-06-29. Retrieved 2021-02-24.
  10. ^ Speight, James G. (2015). Handbook of Petroleum Product Analysis. Hoboken, NJ: Wiley. pp. 158–159. ISBN 978-1-322-95015-0. OCLC 903318141.((cite book)): CS1 maint: date and year (link)
  11. ^ "Hexadecyl". Royal Society of Chemistry. ChemSpider. Retrieved 3 April 2021.
  12. ^ "hexadecyl noun". Merriam-Webster.
  13. ^ Hatanaka, K (2011). Horváth, István T. (ed.). Fluorous Chemistry. Springer Science & Business Media. p. 294. ISBN 9783642252334.
  14. ^ 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.
  15. ^ Pool, G. L.; French, M. E.; Edwards, R. A.; Huang, L.; Lumb, R. H. (1982). "Use of radiolabeled hexadecyl cholesteryl ether as a liposome marker". Lipids. 17 (6): 448–452. doi:10.1007/BF02535225. PMID 7050582. S2CID 42583970.
  16. ^ 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.
  17. ^ Lee, Yanick (July 2017). Radiosynthesis of hexadecyl-4-[ 18F]fluorobenzoate for labeling exosomes and chitosan hydrogels (Master's thesis). Université de Montréal.
  18. ^ "Radioactive cell labeling agent". KR101130737B1. 2012.
  19. ^ 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.
  20. ^ 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.

Cited sources

External links

Alkanes
Category