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Callicarpenal

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Callicarpenal
Names
IUPAC name 3α-Methyl-14a-homo-12-nor-5β,10α-drim-8-en-14a-al
Systematic IUPAC name acetaldehyde
Other names (−)-Callicarpenal; 13,14,15,16-Tetranor-3-cleroden-12-al
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C16H26O/c1-12-6-5-7-14-15(12,3)9-8-13(2)16(14,4)10-11-17/h6,11,13-14H,5,7-10H2,1-4H3/t13-,14+,15+,16+/m1/s1Key: MPWIIQYWQOBNKS-UGUYLWEFSA-N
  • InChI=1/C16H26O/c1-12-6-5-7-14-15(12,3)9-8-13(2)16(14,4)10-11-17/h6,11,13-14H,5,7-10H2,1-4H3/t13-,14+,15+,16+/m1/s1Key: MPWIIQYWQOBNKS-UGUYLWEFBV
SMILES
  • O=CC2(1(/C(=C\CC1)C)(CC2C)C)C
Properties
Chemical formula C16H26O
Molar mass 234.383 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Callicarpenal is a terpenoid that has been isolated from plants of the genus Callicarpa (beautyberry). It acts as an insect repellent against mosquitoes (Aedes aegypti and Anopheles stephensi) and fire ants. It also has activity against ticks (Ixodes scapularis and Amblyomma americanum).

In comparison to the most commonly used insect repellent, DEET, callicarpenal is only about 21% less effective at preventing mosquito bites.

Callicarpenal was discovered by scientists at the United States Department of Agriculture's Agricultural Research Service who were inspired by reports that Callicarpa americana (American beautyberry) was used as a folk remedy to prevent mosquito bites.

References

  1. ^ Cantrell, C. L.; Klun, J. A.; Bryson, C. T.; Kobaisy, M.; Duke, S. O. (2005). "Isolation and Identification of Mosquito Bite Deterrent Terpenoids from Leaves of American (Callicarpa americana) and Japanese (Callicarpa japonica) Beautyberry". Journal of Agricultural and Food Chemistry. 53 (15): 5948–53. doi:10.1021/jf0509308. PMID 16028979.
  2. Chen, J; Cantrell, CL; Duke, SO; Allen, ML (2008). "Repellency of callicarpenal and intermedeol against workers of imported fire ants (Hymenoptera: Formicidae)". Journal of Economic Entomology. 101 (2): 265–71. doi:10.1603/0022-0493(2008)101[265:ROCAIA]2.0.CO;2. PMID 18459387.
  3. Carroll, JF; Cantrell, CL; Klun, JA; Kramer, M (2007). "Repellency of two terpenoid compounds isolated from Callicarpa americana (Lamiaceae) against Ixodes scapularis and Amblyomma americanum ticks". Experimental & Applied Acarology. 41 (3): 215–24. doi:10.1007/s10493-007-9057-2. PMID 17380408. S2CID 13138655.
  4. Ling, Taotao; Xu, Jing; Smith, Ryan; Ali, Abbas; Cantrell, Charles L.; Theodorakis, Emmanuel A. (2011). "Synthesis of (−)-callicarpenal, a potent arthropod repellent". Tetrahedron. 67 (17): 3023–3029. doi:10.1016/j.tet.2011.02.078. PMC 3105892. PMID 21643472.
  5. Luis Pons (February 2006). "Folk Remedy Yields Mosquito-Thwarting Compound". Agricultural Research Magazine. 54 (2).

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