Chrysanthemic acid

Chrysanthemic acid

Chrysanthemic acid
(1R,3R)- or (+)-trans-chrysanthemic acid
CAS number  (1R,3R) or (+)-trans
PubChem  (1R,3R) or (+)-trans,  (1S,3S) or (-)-trans,  (1R,3S) or (+)-cis,  (1S,3R) or (-)-cis
ChemSpider  (+)-trans,  (-)-cis
Jmol-3D images Image 1
Molecular formula C10H16O2
Molar mass 168.23 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)

Chrysanthemic acid is an insecticides. It is related to the pyrethrin I and II, as well as the pyrethroids. One of the four stereoisomers, (1R,3R)- or (+)-trans-chrysanthemic acid (pictured), is the acid part of the ester pyrethrin I, which occurs naturally in the seed cases of Chrysanthemum cinerariaefolium. Many synthetic pyrethroids, for example the allethrins, are esters of all four stereoisomers.


Chrysanthemic acid is derived from its pyrophosphate ester, which in turn is produced naturally from two molecules of dimethylallyl diphosphate.[1]

Industrial synthesis

Chrysanthemic acid is produced industrially in a cyclopropanation reaction of a diene as a mixture of cis- and trans isomers, followed by hydrolysis of the ester:[2]

Chrysanthemic ester synthesis

Many pyrethroids are accessible by re-esterification of chrysanthemic acid ethylester.


  1. ^ Shattuck-Eidens DM, Wrobel WM, Peiser GD, Poulter CD (2001). "Chrysanthemyl diphosphate synthase: isolation of the gene and characterization of the recombinant non-head-to-tail monoterpene synthase from Chrysanthemum cinerariaefolium". Proc. Natl. Acad. Sci. U.S.A. 98 (8): 4373–8.  
  2. ^ A synthesis of chrysanthemic ester: An undergraduate experiment. Kelly, Lawrence F. J. Chem. Educ. 1987, 64, 1061.