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Heneicosane

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Heneicosane
Structural formula of heneicosane
Names
Preferred IUPAC name Henicosane
Other names n-Heneicosane
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1748500
ChEBI
ChemSpider
ECHA InfoCard 100.010.109 Edit this at Wikidata
EC Number
  • 211-118-9
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C21H44/c1-3-5-7-9-11-13-15-17-19-21-20-18-16-14-12-10-8-6-4-2/h3-21H2,1-2H3Key: FNAZRRHPUDJQCJ-UHFFFAOYSA-N
SMILES
  • CCCCCCCCCCCCCCCCCCCCC
Properties
Chemical formula C21H44
Molar mass 296.583 g·mol
Appearance Waxy solid
Density 0.7919 g mL
Melting point 40.5 °C (104.9 °F; 313.6 K)
Boiling point 356.10 °C; 672.98 °F; 629.25 K
Solubility in water 2.9×10 g/L
log P 10.65
Vapor pressure 8.73X10-5 mm Hg
Henry's law
constant (kH) 		120 atm•m/mole
Refractive index (nD) 1.4441
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1 1 0
Flash point 113 °C (235 °F; 386 K)
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Heneicosane is the organic compound with the formula CH3(CH2)19CH3. It is the straight chain, saturated C21 hydrocarbon. It is a white wax.

Natural occurrence

Heneicosane is used as a pheromone by the queen or king termites in the species Reticulitermes flavipes. It also attracts mosquitoes in the genus Aedes and can be used in mosquito baits. This works in nature as the hydrocarbon is produced in the skin of the larva. A 1:100000 fraction in water is the most attractive, but if the concentration is 1:1000 then mosquitoes are repelled instead. Heneicosane is one of the major components of the safflower flower essential oil (Carthamus tinctorius). All parts of the plant Periploca laevigata contain heneicosane. Rosa damascena flower essential oil contains 5% heneicosane. Sambucus nigra contains 2.3%.

References

  1. "Termite queen, king recognition pheromone identified". 19 March 2018. Retrieved 21 March 2018.
  2. Kumar, P; Lomash, V; Jatav, PC; Kumar, A; Pant, SC (January 2016). "Prenatal developmental toxicity study of n-heneicosane in Wistar rats". Toxicology and Industrial Health. 32 (1): 118–25. Bibcode:2016ToxIH..32..118K. doi:10.1177/0748233713498438. PMID 24060842. S2CID 206543815.
  3. Seenivasagan, T; Sharma, KR; Sekhar, K; Ganesan, K; Prakash, S; Vijayaraghavan, R (March 2009). "Electroantennogram, flight orientation, and oviposition responses of Aedes aegypti to the oviposition pheromone n-heneicosane". Parasitology Research. 104 (4): 827–33. doi:10.1007/s00436-008-1263-2. PMID 19018567. S2CID 6880282.
  4. Asgarpanah, J; Kazemivash, N (February 2013). "Phytochemistry, pharmacology and medicinal properties of Carthamus tinctorius L.". Chinese Journal of Integrative Medicine. 19 (2): 153–9. doi:10.1007/s11655-013-1354-5. PMID 23371463. S2CID 386921.
  5. Zito, P; Sajeva, M; Bruno, M; Rosselli, S; Maggio, A; Senatore, F (2013). "Essential oils composition of Periploca laevigata Aiton subsp. angustifolia (Labill.) Markgraf (Apocynaceae-Periplocoideae)". Natural Product Research. 27 (3): 255–65. doi:10.1080/14786419.2012.671319. PMID 22439883. S2CID 205838364.
  6. Sadraei, H; Asghari, G; Emami, S (January 2013). "Inhibitory effect of Rosa damascena Mill flower essential oil, geraniol and citronellol on rat ileum contraction". Research in Pharmaceutical Sciences. 8 (1): 17–23. PMC 3895296. PMID 24459472.
Alkanes


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