Hexadecane

{{chembox|Watchedfields=changed|verifiedrevid=443855529|ImageFile=Hexadecane.svg|ImageFile_Ref={{chemboximage|correct|??}}|ImageSize=280|ImageAlt=Structural formula of hexadecane|ImageFile1=Hexadecane 3D ball.png|ImageFile1_Ref={{chemboximage|correct|??}}|ImageSize1=280|ImageAlt1=Ball-and-stick model of the hexadecane molecule|ImageFile2=Hexadecane 3d.png|PIN=Hexadecane{{PubChem|11006}}

|OtherNames=Cetane

|Section1={{Chembox Identifiers

| CASNo = 544-76-3

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = F8Z00SHP6Q

| PubChem = 11006

| ChemSpiderID = 10540

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 208-878-9

| MeSHName = n-hexadecane

| ChEBI = 45296

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 134994

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| Beilstein = 1736592

| Gmelin = 103739

| SMILES = CCCCCCCCCCCCCCCC

| StdInChI = 1S/C16H34/c1-3-5-7-9-11-13-15-16-14-12-10-8-6-4-2/h3-16H2,1-2H3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = DCAYPVUWAIABOU-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

}}|Section2={{Chembox Properties

| C=16 | H=34

| Appearance = Colourless liquid

| Odor = Gasoline-like to odorless

| Density = 0.77 g/cm³{{GESTIS|ZVG=13200}}

| MeltingPtC = 18.18

| MeltingPt_ref = Haynes, p. 3.294

| BoilingPtC = 286.9

| BoilingPt_ref =

| LogP = 8.859

| VaporPressure = < 0.1 mbar (20 °C)

| HenryConstant = 43 nmol Pa⁻¹ kg⁻¹

| RefractIndex = 1.4329

| MagSus = −187.6·10⁻⁶ cm³/molHaynes, p. 3.578

| Viscosity = 3.03 mPa·sHaynes, p. 6.245

| ThermalConductivity = 0.140 W/(m·K)Haynes, p. 6.256

}}|Section3={{Chembox Thermochemistry

| Thermochemistry_ref =Haynes, p. 5.21

| DeltaHf = −456.1 kJ mol⁻¹

| DeltaHc =

| Entropy =

| HeatCapacity = 501.6 J K⁻¹ mol⁻¹

}}|Section4={{Chembox Hazards

| GHSPictograms = {{gHS exclamation mark}}

| GHSSignalWord = WARNING

| HPhrases = {{h-phrases|315}}

| FlashPtC =136

| FlashPt_ref = Haynes, p. 16.25

| AutoignitionPtC =202

| AutoignitionPt_ref =

}}|Section5={{Chembox Related

| OtherFunction_label = alkanes

| OtherFunction = {{unbulleted list|Pentadecane|Heptadecane}}

}}}}

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. Isohexadecane is a branch chained isomer of hexadecane.https://b4brands.com/resources/ingredient-directory/isohexadecane/#:~:text=Isohexadecane%20is%20a%20branched%2Dchain,that%20is%20found%20in%20petroleum.

Cetane number

Cetane is often used as a shorthand for cetane number, a measure of the combustion of diesel fuel.{{Cite web |title=Cetane |url=http://www.mckinseyenergyinsights.com/resources/refinery-reference-desk/cetane/ |access-date=2021-02-24 |website=www.mckinseyenergyinsights.com |language=en |archive-date=2020-06-29 |archive-url=https://web.archive.org/web/20200629191931/https://www.mckinseyenergyinsights.com/resources/refinery-reference-desk/cetane/ |url-status=live }} 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.{{Cite book |last=Speight |first=James G. |url=https://www.worldcat.org/oclc/903318141 |title=Handbook of Petroleum Product Analysis. |publisher=Wiley |year=2015 |isbn=978-1-322-95015-0 |location=Hoboken, NJ |pages=158–159 |oclc=903318141}}

Hexadecyl radical

Hexadecyl, or cetyl, is an alkyl radical of carbon and hydrogen derived from hexadecane, with formula C₁₆H₃₃ and with mass 225.433,{{cite news |title=Hexadecyl |url=http://www.chemspider.com/Chemical-Structure.150674.html |access-date=3 April 2021 |agency=ChemSpider |publisher=Royal Society of Chemistry}} occurring especially in cetyl alcohol.{{cite news |title=hexadecyl noun |url=https://www.merriam-webster.com/dictionary/hexadecyl |publisher=Merriam-Webster}} It confers strong hydrophobicity on molecules containing it.{{cite book |last1=Hatanaka |first1=K |editor1-last=Horváth |editor1-first=István T. |title=Fluorous Chemistry |date=2011 |publisher=Springer Science & Business Media |page=294 |isbn=9783642252334 |url=https://books.google.com/books?id=7KdIV-iPA5cC&pg=PA294}} Carboplatin modified with hexadecyl and polyethylene glycol has increased liposolubility and PEGylation, proposed to useful in chemotherapy, specifically non-small-cell lung cancer.{{cite journal |doi=10.1080/10717544.2021.1938754|title=Prodrug-based nano-delivery strategy to improve the antitumor ability of carboplatin in vivo and in vitro|year=2021|last1=Lang|first1=Tingting|last2=Li|first2=Nuannuan|last3=Zhang|first3=Jing|last4=Li|first4=Yi|last5=Rong|first5=Rong|last6=Fu|first6=Yuanlei|journal=Drug Delivery|volume=28|issue=1|pages=1272–1280|pmid=34176381|pmc=8238065}}

Hexadecyl was used from 1982 for radiolabelling,{{cite journal |doi=10.1007/BF02535225|title=Use of radiolabeled hexadecyl cholesteryl ether as a liposome marker|year=1982|last1=Pool|first1=G. L.|last2=French|first2=M. E.|last3=Edwards|first3=R. A.|last4=Huang|first4=L.|last5=Lumb|first5=R. H.|journal=Lipids|volume=17|issue=6|pages=448–452|pmid=7050582|s2cid=42583970}} and this continues to be useful,{{cite journal |doi=10.1016/j.bbrep.2017.10.007|title=Radiolabeled cholesteryl ethers: A need to analyze for biological stability before use|year=2018|last1=Manual Kollareth|first1=Denny Joseph|last2=Chang|first2=Chuchun L.|last3=Hansen|first3=Inge H.|last4=Deckelbaum|first4=Richard J.|journal=Biochemistry and Biophysics Reports|volume=13|pages=1–6|pmid=29188234|pmc=5697731}} for example for radiolabelling exosomes and hydrogels,{{cite book |last1=Lee |first1=Yanick |title=Radiosynthesis of hexadecyl-4-[ 18F]fluorobenzoate for labeling exosomes and chitosan hydrogels |date=July 2017 |publisher=Université de Montréal |url=https://papyrus.bib.umontreal.ca/xmlui/bitstream/handle/1866/19446/Lee_Yanick_2017_memoire.pdf?sequence=2&isAllowed=y |format=Master's thesis}}

and for positron emission tomography.{{cite news |title=Radioactive cell labeling agent |url=https://patents.google.com/patent/KR101130737B1/en |work=KR101130737B1 |date=2012}}

Hexadecyl platelet-activating factor has profound effects on the lung,{{cite journal |doi=10.1172/JCI113028|title=Metabolism of platelet-activating factor in isolated perfused rat lung|year=1987|last1=Haroldsen|first1=P. E.|last2=Voelkel|first2=N. F.|last3=Henson|first3=J. E.|last4=Henson|first4=P. M.|last5=Murphy|first5=R. C.|journal=Journal of Clinical Investigation|volume=79|issue=6|pages=1860–1867|pmid=3108322|pmc=424530}} and hexadecyl glyceryl ether participates in the biosynthesis of plasmalogens.{{cite journal |doi=10.1016/0006-291x(70)90697-2|title=Tumor lipids: Biosynthesis of plasmalogens|year=1970|last1=Wood|first1=Randall|last2=Healy|first2=Kathleen|journal=Biochemical and Biophysical Research Communications|volume=38|issue=2|pages=205–211|pmid=5418699}}

References

Cited sources

{{cite book | editor= Haynes, William M. | date = 2016| title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = CRC Press | isbn = 9781498754293}}

External links

[http://ddbonline.ddbst.de/AntoineCalculation/AntoineCalculationCGI.exe?component=Hexadecane Vapor pressure ] and [http://ddbonline.ddbst.de/DIPPR105DensityCalculation/DIPPR105CalculationCGI.exe?component=Hexadecane liquid density] calculation
[https://archive.today/20130102000534/http://www.bepress.com/ijcre/vol9/S3/ Technique to determine hexadecane transfer]

Category:Alkanes