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[edit]

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[edit]

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[edit]

^ 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[edit]

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

External links[edit]

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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Cetane number[edit]

Hexadecyl radical[edit]

See also[edit]

References[edit]

Cited sources[edit]

External links[edit]