Chrysanthemic acid

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Chrysanthemic acid
(1R,3R)- or (+)-trans-chrysanthemic acid
Identifiers
CAS number 4638-92-0 (1R,3R) or (+)-trans
PubChem 16747 (1R,3R) or (+)-trans, 33607 (1S,3S) or (-)-trans, 33606 (1R,3S) or (+)-cis, 20755 (1S,3R) or (-)-cis
ChemSpider 15876 (+)-trans, 19543 (-)-cis
ChEMBL CHEMBL1437285
Jmol-3D images Image 1
Properties
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)
Infobox references

Chrysanthemic acid is an organic compound that is related to a variety of natural and synthetic 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.

Biosynthesis[edit]

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

CCPaseRxn'.png

Industrial synthesis[edit]

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.

References[edit]

  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. doi:10.1073/pnas.071543598. PMC 31842. PMID 11287653. 
  2. ^ A synthesis of chrysanthemic ester: An undergraduate experiment. Kelly, Lawrence F. J. Chem. Educ. 1987, 64, 1061.