Hexadecane

Last updated
Hexadecane
Hexadecane.svg
Hexadecane 3D ball.png
Hexadecane 3d.png
Names
Preferred IUPAC name
Hexadecane [1]
Other names
Cetane
Identifiers
3D model (JSmol)
1736592
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.072 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-878-9
103739
MeSH n-hexadecane
PubChem CID
UNII
  • InChI=1S/C16H34/c1-3-5-7-9-11-13-15-16-14-12-10-8-6-4-2/h3-16H2,1-2H3 Yes check.svgY
    Key: DCAYPVUWAIABOU-UHFFFAOYSA-N Yes check.svgY
  • CCCCCCCCCCCCCCCC
Properties
C16H34
Molar mass 226.448 g·mol−1
AppearanceColourless 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:
GHS-pictogram-exclam.svg
Warning
H304
P301+P316, P331, P405, P501
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).
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Hexadecane (also called cetane) is an alkane hydrocarbon with the chemical formula C 16 H 34. 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. Isohexadecane is a branch chained isomer of hexadecane. [9]

Contents

Cetane number

Cetane is often used as a shorthand for cetane number, a measure of the combustion of diesel fuel. [10] 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. [11]

Hexadecyl radical

Hexadecyl, or cetyl, is an alkyl radical of carbon and hydrogen derived from hexadecane, with formula C16H33 and with mass 225.433, [12] occurring especially in cetyl alcohol. [13] It confers strong hydrophobicity on molecules containing it. [14] Carboplatin modified with hexadecyl and polyethylene glycol has increased liposolubility and PEGylation, and is proposed to useful in chemotherapy, specifically non-small-cell lung cancer. [15]

Hexadecyl was used from 1982 for radiolabelling, [16] and this continues to be useful, [17] for example for radiolabelling exosomes and hydrogels, [18] and for positron emission tomography. [19]

Hexadecyl platelet-activating factor has profound effects on the lung, [20] and hexadecyl glyceryl ether participates in the biosynthesis of plasmalogens. [21]

See also

References

  1. ↑ CID 11006 from PubChem
  2. 1 2 3 4 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. 1 2 Haynes, p. 16.25
  9. ↑ "Isohexadecane - Info, Uses, Side Effects & Dangers".
  10. ↑ "Cetane". McKinsey Energy Insights. Archived from the original on 2020-06-29. Retrieved 2021-02-24.
  11. ↑ Speight, James G. (2015). Handbook of Petroleum Product Analysis. Hoboken, N.J.: Wiley. pp. 158–159. ISBN   978-1-322-95015-0. OCLC   903318141.
  12. ↑ "Hexadecyl". Royal Society of Chemistry. ChemSpider. Retrieved 3 April 2021.
  13. ↑ "hexadecyl noun". Merriam-Webster.
  14. ↑ Hatanaka, K (2011). Horváth, István T. (ed.). Fluorous Chemistry. Springer Science & Business Media. p. 294. ISBN   9783642252334.
  15. ↑ 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.
  16. ↑ 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.
  17. ↑ 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.
  18. ↑ Lee, Yanick (July 2017). Radiosynthesis of hexadecyl-4-[ 18F]fluorobenzoate for labeling exosomes and chitosan hydrogels (PDF) (Master's thesis). Université de Montréal.
  19. ↑ "Radioactive cell labeling agent". Google Patents. 2012.
  20. ↑ 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.
  21. ↑ Wood, Randall; Healy, Kathleen (1970). "Tumor lipids: Biosynthesis of plasmalogens". Biochemical and Biophysical Research Communications. 38 (2): 205–211. Bibcode:1970BBRC...38..205W. doi:10.1016/0006-291x(70)90697-2. PMID   5418699.

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