Chrysanthemum dicarboxylic acid

Chrysanthemum dicarboxylic acid or pyrethric acid may exist in eight stereoisomers, owing to the trans or cis configuration on the side chain of the double bond as well as that of the cyclopropane. The natural acid has been shown to be the trans-trans acid. As in the case of the chrysanthemum monocarboxylic acid, the naturally occurring configuration is more insecticidally active than the racemic form or any of the three isomers synthesized. 

Inouye Y, Takeshita Y, Ohno M (1955) Studies on synthetic pyrethroids V. Synthesis of geometrical isomers of chrysanthemum dicarboxylic acid. Bull Agric Chem Soc Jpn 19 193-199... 

Hagiya et al. recently reported [20] the new decarboxylation catalyst of chrysanthemum dicarboxylic acid monomethyl ester (46) to give ethyl (Z)-norchrysanthemate (EIZ = 4/96) in 59% yield. This method efficiently gives (Z)-(l R)-lrans-norchrysanthemic acid, but the yield is still moderate and the starting chrysanthemum dicarboxylic acid monomethyl ester is not a commercial product (Scheme 7). 

In a recent study, chiral separations for pyrethroic acids, which are the chiral building blocks of synthetic pyrethroids and the primary metabolites of the acid part of these potent ester insecticides, have been developed [62], For example, a polar-organic mobile phase allowed the complete baseline resolution of all four stereoisomers of chrysanthemic acid (2,2-dimethyl-3-(2-methylprop-l-enyl)-cyclopropanecarboxylic acid) on a 0-9-(tcrt-butylcarbamoyl)quinine-based CSP(acjj = 1.20, oLtrans = 1-35, critical Rs = 3.03) (Figure 1,32a). This chiral acid is the precursor of pyrethroids like allethrin, phenothrin, resmethrin, and tetramethrin but not excreted as metabolite. The primary acid metabolite of these pyrethroids is chrysanthemum dicarboxylic acid (3-[(l )-2-carboxyprop-l-enyl]-2,2-dimethylcyclopropanecarboxylic acid) the stereoisomers of which could also be resolved with a reversed-phase eluent (acetonitrile— 30-mM ammonium acetate buffer 90 10, v/v pHa = 6.0) and employing an O-9-(2,6-diisopropylphenylcarbamoyl)quinine-based CSP ads = 1-09, atrans = 1-50,... 

B. ). Fitzsimmons and B. Fraser-Reid, Annulated pyranosides V. An enantiospecilic route to (+) and (-) chrysanthemum dicarboxylic acids, Tetrahedron 40 1279 (1984). 

CAT-REL, vesicular catecholamine release CB-R, cannabinoid receptor CB1-R, CB2-R, cannabinoid receptors CBD, chitin-binding domain CBG, cortisol-binding globulin CBZ-R, central benzodiazepine receptor CCK-R, cholecystokinin receptor CDC, chrysanthemum dicarboxylic acid CDK, cell division kinase, cyclin-dependent protein kinase... 

Fitzsimmons, B J, Fraser-Reid, B, Annulated pyranosides as chiral synthons for carbocyclic systems. Enantiospecific routes to both (-1-)- and (—)-chrysanthemum dicarboxylic acids from a single progenitor, J. Am. Chem. Soc., 101, 6123-6125, 1979. 

Chrysanthemum dicarboxylic acid monomethyl ester pyrethrolone Chrysanthemum dicarboxylic acid monomethyl ester pyrethrolone ester. See Pyrethrin II Chrysanthemum monocarboxylic acid pyrethrolone ester. See Pyrethrin I Chrysoidin Chrysoidine Chrysoidine crystals Chrysoidine special. See Basic orange 2 Chrysoine. See Acid orange 6 Chrysophanic acid... 

Synonyms Chrysanthemum dicarboxylic acid monomethyl ester pyrethrolone Chrysanthemum dicarboxylic acid monomethyl ester pyrethrolone ester Cyclopropaneacrylic acid, 3-carboxy-a,2,2-trimethyl-, 1-methyl ester, ester with 4-hydroxy-3-methyl-2-(2,4-pentadienyl)-2-cyclopenten-1-one Pyrethrin Pyrethrolone, chrysanthemum dicarboxylic acid methyl ester ester... 

Pyrethrolone ester of chrysanthemum dicarboxylic acid monomethyl ester (+)-Pyrethronyl ( ( )-pyrethrate Pyretrin II... 

In the past carbohydrates have often proved useful as enantiomerically well defined starting materials. Now Fraser-Reid and Fitzsimmons have utilized (24) as starting material in a synthesis of both of the enantiomers of chrysanthemic acid in an optically pure state. ° The chrysanthemum dicarboxylic acid analogue (26)... 

Chrysanthemum dicarboxylic acid In Table B32, Appendix B, the four isomers arising from the oxidation/hydrolysis of allethrin, fenpropathrin, phenothrin, and resmethrin are listed. Oxidation of the parent molecule may occur prior to hydrolysis, or hydrolysis may occur followed by oxidation. 

Chrysanthemum dicarhoxylic acid Chrysanthemum dicarboxylic acid, 3-[(lE)-2-carboxyprop-l-enyl]-2,2-dimethylcyclopropanecarboxylic acid CAS no. 497-95-0 (generic)... 

Table B32 Chrysanthemum dicarboxylic acid, individual isomers...

See Table 3 (3.2) for generic structure and technical name of chrysanthemum dicarboxylic acid OR = Optical rotation NA = Not available... 

Pyrethrum flower consists of the dried flowerhead of Chrysanthemum cinerar ice folium Vis. and it owes its insecticidal properties to two types of ketoesters. One group consists of pyrethrin I and cinerin I, both of which have chrysanthemum monocarboxylic acid (chrysanthemic acid) as their acid component. The assay given below for pyrethrin I, which is based on the determination of total chrysanthemic acid, will therefore include cinerin I. The second group of esters consists of pyrethrin II and cinerin II, both of which have the monomethyl ester of chrysanthemum dicarboxylic acid (pyrethric acid) as their acid component since the assay given below for pyrethrin II is based on the determination of total pyrethric acid it will therefore include cinerin II. The keto-alcohol component of the pyrethrins is pyrethrolone and that of the cinerins is cinerolone. 

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