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Callicarpenal

Callicarpenal
Names
IUPAC name
3α-Methyl-14a-homo-12-nor-5β,10α-drim-8-en-14a-al
Systematic 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
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]

References

  1. ^ a b 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. Bibcode:2005JAFC...53.5948C. 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.[dead link]
  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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