Surf Wiki
Save to docs
general/monoterpenes

From Surf Wiki (app.surf) — the open knowledge base

Chrysanthemic acid

Chrysanthemic acid

Chrysanthemic acid is an organic compound that is related to a variety of natural and synthetic insecticides. It is a terpenoic acid 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. Staudinger and Ružička named chrysanthemic acid in 1924.

Biosynthesis

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

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:

Chrysanthemic ester synthesis

Many pyrethroids are accessible by re-esterification of chrysanthemic acid ethyl ester - a perfume ingredient.

References

References

  1. (2001). "Fascinating Natural and Artificial Cyclopropane Architectures". Angewandte Chemie International Edition.
  2. H. Staudinger, L. Ružička: "Insektentotende Stoffe H. Zur Konstitution der Chrysanthemummonocarbonsiiure und -dicarbonsiiure", Helv. Chem. Acta 7 (1924) 201
  3. (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..
  4. Kelly Lawrence F. (1987). "A synthesis of chrysanthemic ester: An undergraduate experiment". J. Chem. Educ..
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

monoterpenes cyclopropanes carboxylic-acids
Want to explore this topic further?

Ask Mako anything about Chrysanthemic acid — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report