Chrysanthemic acid

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Chrysanthemic acid
(1R,3R)- or (+)-trans-chrysanthemic acid
Names
IUPAC name
2,2-Dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylic acid
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
ECHA InfoCard
100.022.788 Edit this at Wikidata
  • 16747 (1R,3R) or (+)-trans
  • 33607 (1S,3S) or (−)-trans
  • 33606 (1R,3S) or (+)-cis
  • 20755 (1S,3R) or (−)-cis
UNII
  • InChI=1S/C10H16O2/c1-6(2)5-7-8(9(11)12)10(7,3)4/h5,7-8H,1-4H3,(H,11,12)/t7-,8+/m0/s1
    Key: XLOPRKKSAJMMEW-JGVFFNPUSA-N
  • CC(=CC1C(C1(C)C)C(=O)O)C
Properties
C10H16O2
Molar mass 168.236 g·mol−1
Melting point 17 °C (63 °F; 290 K) (1R,3R) or (+)-trans
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Chrysanthemic acid is an

allethrins, are esters of all four stereoisomers.[1] Staudinger and Ružička named chrysanthemic acid in 1924.[2]

Biosynthesis

Chrysanthemic acid is derived from its

Industrial synthesis

Chrysanthemic acid is produced industrially in a

cis- and trans isomers, followed by hydrolysis of the ester:[4]

Chrysanthemic ester synthesis

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

References

  1. PMID 11433485
    .
  2. ^ H. Staudinger, L. Ružička: "Insektentotende Stoffe H. Zur Konstitution der Chrysanthemummonocarbonsiiure und -dicarbonsiiure", Helv. Chem. Acta 7 (1924) 201
  3. PMID 11287653
    .
  4. .