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
CAS Number	161105-12-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	9282422;
PubChem CID	11107286;
UNII	HX4WCL7DPK ;
CompTox Dashboard (EPA)	DTXSID00455470 ;
	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/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;
	SMILES O=CC[C@@]2([C@@H]1[C@](/C(=C\CC1)C)(CC[C@H]2C)C)C;
Properties
Chemical formula	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). Infobox references

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]

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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