Heneicosane

Heneicosane
Structural formula of heneicosane
Names
Preferred IUPAC name
Henicosane
Other names
n-Heneicosane
Identifiers
3D model (JSmol)
1748500
ChEBI
ChemSpider
ECHA InfoCard 100.010.109 Edit this at Wikidata
EC Number
  • 211-118-9
UNII
  • InChI=1S/C21H44/c1-3-5-7-9-11-13-15-17-19-21-20-18-16-14-12-10-8-6-4-2/h3-21H2,1-2H3 checkY
    Key: FNAZRRHPUDJQCJ-UHFFFAOYSA-N checkY
  • CCCCCCCCCCCCCCCCCCCCC
Properties
C21H44
Molar mass 296.583 g·mol−1
Appearance Waxy solid
Density 0.7919 g mL−1
Melting point 40.5 °C (104.9 °F; 313.6 K)
Boiling point 356.10 °C; 672.98 °F; 629.25 K
2.9×10−11 g/L
log P 10.65
Vapor pressure 8.73X10-5 mm Hg
120 atm•m3/mole
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 [77 °F], 100 kPa).

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.[1] It also attracts mosquitoes in the genus Aedes and can be used in mosquito baits.[2] 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.[3] Heneicosane is one of the major components of the safflower flower essential oil (Carthamus tinctorius).[4] All parts of the plant Periploca laevigata contain heneicosane.[5] Rosa damascena flower essential oil contains 5% heneicosane.[6] 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.


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