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Hexadecane

From Wikipedia, the free encyclopedia
"Cetane" redirects here. For the diesel fuel analysis, seeCetane number.
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 InfoCard100.008.072Edit this at Wikidata
EC Number
  • 208-878-9
103739
MeSHn-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 mass226.448 g·mol−1
AppearanceColourless liquid
OdorGasoline-like to odorless
Density0.77 g/cm3[2][3]
Melting point18.18 °C (64.72 °F; 291.33 K)[2]
Boiling point286.9 °C (548.4 °F; 560.0 K)[2]
logP8.859
Vapor pressure< 0.1 mbar (20 °C)
43 nmol Pa−1 kg−1
−187.6·10−6 cm3/mol[4]
Thermal conductivity0.140 W/(m·K)[5]
1.4329[2]
Viscosity3.03 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 point136 °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 theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Hexadecane (also calledcetane) is analkanehydrocarbon with thechemical formula C16H34. Hexadecane consists of a chain of 16carbon atoms, with threehydrogen atoms bonded to the two end carbon atoms, and two hydrogens bonded to each of the 14 other carbon atoms.

Cetane number

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Main article:Cetane number

Cetane is often used as a shorthand forcetane number, a measure of the combustion ofdiesel 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

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Hexadecyl is analkylradical ofcarbon andhydrogen derived from hexadecane, with formula C16H33 and with mass 225.433,[11] occurring especially incetyl alcohol.[12] It confers strong hydrophobicity on molecules containing it.[13]Carboplatin modified with hexadecyl andpolyethylene glycol has increasedliposolubility andPEGylation, proposed to useful inchemotherapy, specificallynon-small-cell lung cancer.[14]

Hexadecyl was used from 1982 forradiolabelling,[15] and this continues to be useful,[16] for example for radiolabellingexosomes andhydrogels,[17]and forpositron emission tomography.[18]

Hexadecylplatelet-activating factor has profound effects on the lung,[19] and hexadecyl glyceryl ether participates in thebiosynthesis ofplasmalogens.[20]

See also

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References

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  1. ^CID 11006 fromPubChem
  2. ^abcdHaynes, p. 3.294
  3. ^Record in theGESTIS Substance Database of theInstitute 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. ^abHaynes, p. 16.25
  9. ^"Cetane".www.mckinseyenergyinsights.com.Archived from the original on 2020-06-29. Retrieved2021-02-24.
  10. ^Speight, James G. (2015).Handbook of Petroleum Product Analysis. Hoboken, NJ: Wiley. pp. 158–159.ISBN 978-1-322-95015-0.OCLC 903318141.
  11. ^"Hexadecyl". Royal Society of Chemistry. ChemSpider. Retrieved3 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

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External links

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