Hexadecane: Difference between revisions
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{{main|Cetane number}} |
{{main|Cetane number}} |
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''Cetane'' is often used as a shorthand for [[cetane number]], a measure of the combustion of [[diesel fuel]].<ref name="McKinsey">{{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 }}</ref> 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.<ref name="Speight2015">{{Cite book |last=Speight |first=James G. |url=https://www.worldcat.org/oclc/903318141 |title=Handbook of Petroleum Product Analysis. |date=2015 |publisher=Wiley |year=2015 |isbn=978-1-322-95015-0 |location=Hoboken, NJ |pages=158–159 |oclc=903318141}}</ref> |
''Cetane'' is often used as a shorthand for [[cetane number]], a measure of the combustion of [[diesel fuel]].<ref name="McKinsey">{{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 }}</ref> 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.<ref name="Speight2015">{{Cite book |last=Speight |first=James G. |url=https://www.worldcat.org/oclc/903318141 |title=Handbook of Petroleum Product Analysis. |date=2015 |publisher=Wiley |year=2015 |isbn=978-1-322-95015-0 |location=Hoboken, NJ |pages=158–159 |oclc=903318141}}</ref> |
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==Hexadecyl== |
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Hexadecyl is a functional group chain [[radical]] of [[carbon]] and [[hydrogen]], with formula C<sub>16</sub>H<sub>33</sub> and with mass 225.433.<ref name="csh">{{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}}</ref> It is "an [[alkyl]] [[radical (chemistry)|radical]] derived from a [[hexadecane]]," especially a [[cetyl]].<ref name="mwh">{{cite news |title=hexadecyl noun |url=https://www.merriam-webster.com/dictionary/hexadecyl |publisher=Merriam-Webster}}</ref> It is a noted hydrophobe.<ref name="horvath11">{{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}}</ref> |
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The substance synthesized by Hexadecyl, [[Carboplatin]] and [[polyethylene glycol]] appears to have increased [[liposolubility]] and [[PEGylation]] qualities. This may be useful in [[chemotherapy]], specifically non-small cell [[lung cancer]].<ref name="lang21">{{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}}</ref> |
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Hexadecyl was noted as early as 1982 for its role in [[radiolabelling]].<ref name="pool82">{{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}}</ref> The technique of which it forms a vital part has continued to be useful even as late as 2017.<ref name="kollareth17">{{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}}</ref> In fact, it is useful to radiolabel [[exosome (vesicle)|exosomes]] and [[hydrogels]].<ref name="lee17">{{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}}</ref> |
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Hexadecyl is a bridge molecule important for [[positron emission tomography]].<ref name="krpat">{{cite news |title=Radioactive cell labeling agent |url=https://patents.google.com/patent/KR101130737B1/en |work=KR101130737B1 |date=2012}}</ref> |
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Hexadecyl [[platelet-activating factor]] "has profound effects on the lung".<ref name="haroldsen87">{{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}}</ref> |
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Hexadecyl and [[octadecyl]] groups are favoured by some in the production of [[Lysophosphatidic acid]].<ref name="hlpa">{{cite news |title=USPTO 20060264361}}</ref> |
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Hexadecyl glyceryl ether is important in the [[biosynthesis]] of [[plasmalogens]].<ref name="wood70">{{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}}</ref> |
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==See also== |
==See also== |
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Revision as of 08:49, 4 August 2021
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| Names | |
|---|---|
| Preferred IUPAC name
Hexadecane[1] | |
| Other names
Cetane
| |
| Identifiers | |
3D model (JSmol)
|
|
| 1736592 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.008.072 |
| EC Number |
|
| 103739 | |
| MeSH | n-hexadecane |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C16H34 | |
| Molar mass | 226.448 g·mol−1 |
| Appearance | Colourless liquid |
| Odor | Gasoline-like to odorless |
| Density | 0.77 g/cm3[2] |
| Melting point | 18 °C (64 °F; 291 K)[2] |
| Boiling point | 287 °C (549 °F; 560 K)[2] |
| log P | 8.859 |
| Vapor pressure | < 0.1 mbar (20 °C) |
Henry's law
constant (kH) |
43 nmol Pa−1 kg−1 |
| -187.63·10−6 cm3/mol | |
Refractive index (nD)
|
1.434 |
| Thermochemistry | |
Heat capacity (C)
|
499.72 J K−1 mol−1 or 2.21 J K−1 g−1 |
Std molar
entropy (S⦵298) |
586.18 J K−1 mol−1 |
Std enthalpy of
formation (ΔfH⦵298) |
−458.3–−454.3 kJ mol−1 |
Std enthalpy of
combustion (ΔcH⦵298) |
−10.7009–−10.6973 MJ mol−1 |
| Hazards | |
| GHS labelling: | |
| |
| Warning | |
| H315 | |
| Flash point | 135 °C (275 °F; 408 K)[2] |
| 215 °C (419 °F; 488 K)[2] | |
| Related compounds | |
Related alkanes
|
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
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.[3] 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.[4]
Hexadecyl
Hexadecyl is a functional group chain radical of carbon and hydrogen, with formula C16H33 and with mass 225.433.[5] It is "an alkyl radical derived from a hexadecane," especially a cetyl.[6] It is a noted hydrophobe.[7]
The substance synthesized by Hexadecyl, Carboplatin and polyethylene glycol appears to have increased liposolubility and PEGylation qualities. This may be useful in chemotherapy, specifically non-small cell lung cancer.[8]
Hexadecyl was noted as early as 1982 for its role in radiolabelling.[9] The technique of which it forms a vital part has continued to be useful even as late as 2017.[10] In fact, it is useful to radiolabel exosomes and hydrogels.[11]
Hexadecyl is a bridge molecule important for positron emission tomography.[12]
Hexadecyl platelet-activating factor "has profound effects on the lung".[13]
Hexadecyl and octadecyl groups are favoured by some in the production of Lysophosphatidic acid.[14]
Hexadecyl glyceryl ether is important in the biosynthesis of plasmalogens.[15]
See also
References
- ^ CID 11006 from PubChem
- ^ a b c d e Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ "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.
{{cite book}}: CS1 maint: date and year (link) - ^ "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.
- ^ "USPTO 20060264361".
- ^ 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.
External links
- Vapor pressure and liquid density calculation
- Technique to determine hexadecane transfer