Hexadecane

Last updated
Hexadecane
Hexadecane.svg
Hexadecane 3D ball.png
Hexadecane 3d.png
Names
Preferred IUPAC name
Hexadecane [1]
Other names
Cetane
Identifiers
3D model (JSmol)
1736592
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.072 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-878-9
103739
MeSH n-hexadecane
PubChem CID
UNII
  • InChI=1S/C16H34/c1-3-5-7-9-11-13-15-16-14-12-10-8-6-4-2/h3-16H2,1-2H3 Yes check.svgY
    Key: DCAYPVUWAIABOU-UHFFFAOYSA-N Yes check.svgY
  • CCCCCCCCCCCCCCCC
Properties
C16H34
Molar mass 226.448 g·mol−1
AppearanceColourless liquid
Odor Gasoline-like to odorless
Density 0.77 g/cm3 [2] [3]
Melting point 18.18 °C (64.72 °F; 291.33 K) [2]
Boiling point 286.9 °C (548.4 °F; 560.0 K) [2]
log P 8.859
Vapor pressure < 0.1 mbar (20 °C)
43 nmol Pa−1 kg−1
-187.6·10−6 cm3/mol [4]
Thermal conductivity 0.140 W/(m·K) [5]
1.4329 [2]
Viscosity 3.03 mPa·s [6]
Thermochemistry [7]
501.6 J K−1 mol−1
−456.1 kJ mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315
Flash point 136 °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 their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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]

See also

Related Research Articles

<span class="mw-page-title-main">Alkane</span> Type of saturated hydrocarbon compound

In organic chemistry, an alkane, or paraffin, is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which all the carbon–carbon bonds are single. Alkanes have the general chemical formula CnH2n+2. The alkanes range in complexity from the simplest case of methane, where n = 1, to arbitrarily large and complex molecules, like pentacontane or 6-ethyl-2-methyl-5-(1-methylethyl) octane, an isomer of tetradecane.

<span class="mw-page-title-main">Ether</span> Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R)

In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two organyl groups. They have the general formula R−O−R′, where R and R′ represent organyl groups. Ethers can again be classified into two varieties: if the organyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether". Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula CH3. In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many organic compounds. It is a very stable group in most molecules. While the methyl group is usually part of a larger molecule, bounded to the rest of the molecule by a single covalent bond, it can be found on its own in any of three forms: methanide anion, methylium cation or methyl radical. The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed.

<span class="mw-page-title-main">Haloalkane</span> Group of chemical compounds derived from alkanes containing one or more halogens

The haloalkanes are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially. They are used as flame retardants, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins. For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes that contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see Halomethane. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen.

<span class="mw-page-title-main">Steroid</span> Polycyclic organic compound having sterane as a core structure

A steroid is an organic compound with four fused rings arranged in a specific molecular configuration.

In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term alkyl is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of −CnH2n+1. A cycloalkyl group is derived from a cycloalkane by removal of a hydrogen atom from a ring and has the general formula −CnH2n−1. Typically an alkyl is a part of a larger molecule. In structural formulae, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is methyl, with the formula −CH3.

In chemical nomenclature, the IUPAC nomenclature of organic chemistry is a method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It is published in the Nomenclature of Organic Chemistry. Ideally, every possible organic compound should have a name from which an unambiguous structural formula can be created. There is also an IUPAC nomenclature of inorganic chemistry.

<span class="mw-page-title-main">Catenation</span> Bonding of atoms of the same element into chains or rings

In chemistry, catenation is the bonding of atoms of the same element into a series, called a chain. A chain or a ring shape may be open if its ends are not bonded to each other, or closed if they are bonded in a ring. The words to catenate and catenation reflect the Latin root catena, "chain".

In organic chemistry, a substituent is one or a group of atoms that replaces atoms, thereby becoming a moiety in the resultant (new) molecule.

<span class="mw-page-title-main">Carboplatin</span> Medication used to treat cancer

Carboplatin, sold under the brand name Paraplatin among others, is a chemotherapy medication used to treat a number of forms of cancer. This includes ovarian cancer, lung cancer, head and neck cancer, brain cancer, and neuroblastoma. It is used by injection into a vein.

Cyclopentane (also called C pentane) is a highly flammable alicyclic hydrocarbon with chemical formula C5H10 and CAS number 287-92-3, consisting of a ring of five carbon atoms each bonded with two hydrogen atoms above and below the plane. It occurs as a colorless liquid with a petrol-like odor. Its freezing point is −94 °C and its boiling point is 49 °C. Cyclopentane is in the class of cycloalkanes, being alkanes that have one or more carbon rings. It is formed by cracking cyclohexane in the presence of alumina at a high temperature and pressure.

In the nomenclature of organic chemistry, a locant is a term to indicate the position of a functional group or substituent within a molecule.

<span class="mw-page-title-main">Glycerophospholipid</span> Class of lipids

Glycerophospholipids or phosphoglycerides are glycerol-based phospholipids. They are the main component of biological membranes in eukaryotic cells. They are a type of lipid, of which its composition affects membrane structure and properties. Two major classes are known: those for bacteria and eukaryotes and a separate family for archaea.

<span class="mw-page-title-main">Plasmalogen</span> Subclass of Glycerophospholipids

Glycerophospholipids of biochemical relevance are divided into three subclasses based on the substitution present at the sn-1 position of the glycerol backbone: acyl, alkyl and alkenyl. Of these, the alkyl and alkenyl moiety in each case form an ether bond, which makes for two types of ether phospholipids, plasmanyl, and plasmenyl. Plasmalogens are plasmenyls with an ester linked lipid at the sn-2 position of the glycerol backbone, chemically designated 1-0(1Z-alkenyl)-2-acyl-glycerophospholipids. The lipid attached to the vinyl ether at sn-1 can be C16:0, C18:0, or C18:1, and the lipid attached to the acyl group at sn-2 can be C22:6 ω-3 or C20:4 ω-6, . Plasmalogens are classified according to their head group, mainly as PC plasmalogens (plasmenylcholines) and PE plasmalogens (plasmenylethalomines) Plasmalogens should not be confused with plasmanyls.

<span class="mw-page-title-main">Ether lipid</span>

In biochemistry, an ether lipid refers to any lipid in which the lipid "tail" group is attached to the glycerol backbone via an ether bond at any position. In contrast, conventional glycerophospholipids and triglycerides are triesters. Structural types include:

Higher alkanes are alkanes having nine or more carbon atoms. Nonane is the lightest alkane to have a flash point above 25 °C, and is not classified as dangerously flammable.

In chemistry, a carbonium ion is any cation that has a pentacoordinated carbon atom. The name carbonium may also be used for the simplest member of the class, properly called methanium, where the carbon atom is covalently bonded to five hydrogen atoms.

<span class="mw-page-title-main">Radioactivity in the life sciences</span>

Radioactivity is generally used in life sciences for highly sensitive and direct measurements of biological phenomena, and for visualizing the location of biomolecules radiolabelled with a radioisotope.

<span class="mw-page-title-main">2-Methylpentane</span> Chemical compound

2-Methylpentane, trivially known as isohexane, is a branched-chain alkane with the molecular formula C6H14. It is a structural isomer of hexane composed of a methyl group bonded to the second carbon atom in a pentane chain. Using a quantitative structure-activity relationship (QSAR) prediction model, 2-Methylpentane has a research octane number (RON) of 75, motor octane number (MON) of 77, and cetane number (CN) of 29.

<span class="mw-page-title-main">Dicycloplatin</span> Chemical compound

Dicycloplatin is a chemotherapy medication used to treat a number of cancers which includes the non-small-cell lung carcinoma and prostate cancer.

References

  1. CID 11006 from PubChem
  2. 1 2 3 4 Haynes, p. 3.294
  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
  8. 1 2 Haynes, p. 16.25
  9. "Cetane". www.mckinseyenergyinsights.com. Archived from the original on 2020-06-29. Retrieved 2021-02-24.
  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. Retrieved 3 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