Hexadecane

Hexadecane
Names
	Preferred IUPAC name Hexadecane
	Other names Cetane
Identifiers
CAS Number	544-76-3 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1736592
ChEBI	CHEBI:45296 ;
ChEMBL	ChEMBL134994 ;
ChemSpider	10540 ;
ECHA InfoCard	100.008.072
EC Number	208-878-9;
Gmelin Reference	103739
MeSH	n-hexadecane
PubChem CID	11006;
UNII	F8Z00SHP6Q ;
CompTox Dashboard (EPA)	DTXSID0027195 ;
	InChI InChI=1S/C16H34/c1-3-5-7-9-11-13-15-16-14-12-10-8-6-4-2/h3-16H2,1-2H3 Key: DCAYPVUWAIABOU-UHFFFAOYSA-N ;
	SMILES CCCCCCCCCCCCCCCC;
Properties
Chemical formula	C16H34
Molar mass	226.448 g·mol−1
Appearance	Colourless liquid
Odor	Gasoline-like to odorless
Density	0.77 g/cm3
Melting point	18.18 °C (64.72 °F; 291.33 K)
Boiling point	286.9 °C (548.4 °F; 560.0 K)
log P	8.859
Vapor pressure	< 0.1 mbar (20 °C)
Henry's law; constant (kH)	43 nmol Pa−1 kg−1
Magnetic susceptibility (χ)	-187.6·10−6 cm3/mol
Thermal conductivity	0.140 W/(m·K)
Refractive index (nD)	1.4329
Viscosity	3.03 mPa·s
Thermochemistry
Heat capacity (C)	501.6 J K−1 mol−1
Std enthalpy of; formation (ΔfH⦵298)	−456.1 kJ mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315
Flash point	136 °C (277 °F; 409 K)
Autoignition; temperature	202 °C (396 °F; 475 K)
Related compounds
Related alkanes	Pentadecane; Heptadecane;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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

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]

References

^ CID 11006 from PubChem
^ ^a ^b ^c ^d Haynes, p. 3.294
^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
^ Haynes, p. 3.578
^ Haynes, p. 6.256
^ Haynes, p. 6.245
^ Haynes, p. 5.21
^ ^a ^b Haynes, p. 16.25
^ "Cetane". www.mckinseyenergyinsights.com. Archived from the original on 2020-06-29. Retrieved 2021-02-24.
^ 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.
^ 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.
^ 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.

Cited sources

Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. ISBN 9781498754293.

External links

Vapor pressure and liquid density calculation
Technique to determine hexadecane transfer

[1] CID 11006 from PubChem

[CRC-2] Haynes, p. 3.294

[GESTIS-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

[CRC2-8] Haynes, p. 16.25

[McKinsey-9] "Cetane". www.mckinseyenergyinsights.com. Archived from the original on 2020-06-29. Retrieved 2021-02-24.

[Speight2015-10] Speight, James G. (2015). Handbook of Petroleum Product Analysis. Hoboken, NJ: Wiley. pp. 158–159. ISBN 978-1-322-95015-0. OCLC 903318141.

[csh-11] "Hexadecyl". Royal Society of Chemistry. ChemSpider. Retrieved 3 April 2021.

[mwh-12] "hexadecyl noun". Merriam-Webster.

[horvath11-13] Hatanaka, K (2011). Horváth, István T. (ed.). Fluorous Chemistry. Springer Science & Business Media. p. 294. ISBN 9783642252334.

[lang21-14] 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.

[pool82-15] 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.

[kollareth17-16] 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.

[lee17-17] Lee, Yanick (July 2017). Radiosynthesis of hexadecyl-4-[ 18F]fluorobenzoate for labeling exosomes and chitosan hydrogels (Master's thesis). Université de Montréal.

[krpat-18] "Radioactive cell labeling agent". KR101130737B1. 2012.

[haroldsen87-19] 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.

[wood70-20] 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.

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