Chrysanthemum carboxylic acid

Crombie L, Harper SH (1954) The chrysanthemum carboxylic acids. VI. The configurations of the chrysanthemic acids. J Chem Soc 470... 

B. J. Fitzsimmons and B. Fraser-Reid, Annulated pyranosides as chiral synthons for carbo-cyclic systems. Enantiospecific routes to both (+) and (-) chrysanthemum carboxylic acids from a single progenitor, J. Am. Chem. Soc. 101 6123 (1979). 

Numerous studies of the photoreactions of dihydrofurans have been described. On irradiation 2,3-dihydrofurans are known to undergo conversion to acylcyclopropanes by a pathway involving initial carbon-oxygen bond homolysis. The /i-enamino ester (162), for example, affords the cyclopropane (163) on triplet-sensitized irradiation.138 Similar transformations have been observed in 2,2,4-triacyl-2,3-dihydrofurans,139 and a synthesis of a cis-trans mixture of chrysanthemum carboxylic acid has been accomplished in this way.140 The conversion of the 2-thiazolines(164) to the iV-alkenylthio-amides (165) presumably involves an analogous carbon-sulfur bond homolysis, followed by a 1,2-hydrogen shift in the resulting biradical (166).141... 

Chrysanthemum carboxylic acid esters. Chrysanthemum monocarboxylic acid (CMC) and dicarboxylic acid (CDC) esters include the toxic cinerins and pyrethrins from... 

Pyrethrum (Chrysanthemum) dnerarifolium (Asteraceae) namely cinerin I (CMC cineralone ester), cinerin II (CDC monomethyl ester cinerolone ester), pyrethrin I (CMC pyrethrolone ester) and pyrethrin II (CDC monomethyl ester pyrethrolone ester). The chrysanthemum carboxylic acids are cyclopropane-based monoterpenes and cineralone and pyrethrolone are cyclopentanone monoterpene alcohols. The pyrethrins (and their insecticidal synthetic derivatives) are toxic to insects through keeping cell membrane voltage-gated Na+ channels open and thus impairing neurotransmission. 

Certain bacteria are able to form C3Q, C45, and CgQ-isoprenoids of the phytoene type in addition to phytoene by head-to-head condensation of appropriate precursor molecules. In higher plants certain monoterpenes probably are synthesized in a similar manner. Chrysanthemyl alcohol, occurring in Compositae, is an analog of presqualene and prephytoene. The C-skeletons given in Fig. 97 are derived from chrysanthemyl pyrophosphate. Chrysanthemum carboxylic acid is a constituent of the pyrethrins, compounds with marked insecticidal activity (E 5.5.3). 

Furethrin, furfurylrethronyl ester of chrysanthemum mono-carboxylic acid... 

Beilstein Handbook Reference) BRN 2004306 Caswell No. 715 Chrysanthemum mono-carboxylic acid pyrethrolone ester EINECS 204-455-8 EPA Pesticide Chemical d)de 069001 HSDB 6302 Piretrina 1 Pyrethrin I Pyrethrine I Pyrethrins Pyrethrolone, chrysanthemum monocarboxylic acid ester Pyrethronyl (+)-trans-chrysanthemate Pyrethrum RCRA waste number POOS. Registered by EPA as an insecticide. Viscous liquid bpo.1 = 170° d = 1.5192 [a]8 -14° (isooctane) km = 225 nm (e 36400 95% EtOH) insoluble in H2O, soluble in ElOH, petroleum ether, kerosene, CCI4, ethylene dichloride, nitromethane LDso (rat orl) = 584 - 900 mg/kg, (mus orl) = 273 - 796 mg/kg, (rat der) > 1500 mg/kg, (rbt der) = 5000 mg/kg highly toxic to fish toxic to bees, with repellent effect. 

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