Callicarpenal

Last updated
Callicarpenal
Callicarpenal.svg
Names
Preferred IUPAC name
[(1S,2R,4aR,8aR)-1,2,4a,5-Tetramethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]acetaldehyde
Other names
(−)-Callicarpenal; 13,14,15,16-Tetranor-3-cleroden-12-al
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • 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/s1
    Key: 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/s1
    Key: MPWIIQYWQOBNKS-UGUYLWEFBV
  • O=CC[C@@]2([C@@H]1[C@](/C(=C\CC1)C)(CC[C@H]2C)C)C
Properties
C16H26O
Molar mass 234.383 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Callicarpenal is a terpenoid that has been isolated from plants of the genus Callicarpa (beautyberry). [1] It acts as an insect repellent against mosquitoes ( Aedes aegypti and Anopheles stephensi ) and fire ants. [1] [2] It also has activity against ticks ( Ixodes scapularis and Amblyomma americanum ). [3]

In comparison to the most commonly used insect repellent, DEET, callicarpenal is only about 21% less effective at preventing mosquito bites. [4]

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. [5]

Related Research Articles

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<span class="mw-page-title-main">Insect repellent</span> Substance which repels insects

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Callicarpa americana, the American beautyberry, is an open-habitat, native shrub of the Southern United States which is often grown as an ornamental in gardens and yards. American beautyberries produce large clusters of purple berries, which birds and deer eat, thus distributing the seeds.

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<i>Callicarpa</i> Genus of flowering plants

Callicarpa (beautyberry) is a genus of shrubs and small trees in the family Lamiaceae. They are native to east and southeast Asia, Australia, Madagascar, southeast North America and South America.

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References

  1. 1 2 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).