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.[1]Staudinger and Ružička named chrysanthemic acid in 1924.[2]
Many pyrethroids are accessible by re-esterification of chrysanthemic acid ethylester.
Referencesedit
^Faust, Rüdiger (2001). "Fascinating Natural and Artificial Cyclopropane Architectures". Angewandte Chemie International Edition. 40 (12): 2251–2253. doi:10.1002/1521-3773(20010618)40:12<2251::AID-ANIE2251>3.0.CO;2-R. PMID 11433485.
^H. Staudinger, L. Ružička: "Insektentotende Stoffe H. Zur Konstitution der Chrysanthemummonocarbonsiiure und -dicarbonsiiure", Helv. Chem. Acta 7 (1924) 201
^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. Bibcode:2001PNAS...98.4373R. doi:10.1073/pnas.071543598. PMC31842. PMID 11287653.
^Kelly Lawrence F (1987). "A synthesis of chrysanthemic ester: An undergraduate experiment". J. Chem. Educ. 64 (12): 1061. Bibcode:1987JChEd..64.1061K. doi:10.1021/ed064p1061.
April 14, 2024
chrysanthemic, acid, organic, compound, that, related, variety, natural, synthetic, insecticides, related, pyrethrin, well, pyrethroids, four, stereoisomers, trans, chrysanthemic, acid, pictured, acid, part, ester, pyrethrin, which, occurs, naturally, seed, ca. 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 1 Staudinger and Ruzicka named chrysanthemic acid in 1924 2 Chrysanthemic acid NamesIUPAC name 2 2 Dimethyl 3 2 methylprop 1 enyl cyclopropane 1 carboxylic acidIdentifiersCAS Number 4638 92 0 1R 3R or trans Y2259 14 5 1S 3S or trans Y26771 11 9 1R 3S or cis Y26771 06 2 1S 3R or cis Y3D model JSmol Interactive imageChEMBL ChEMBL1437285ChemSpider 15876 trans19543 cisECHA InfoCard 100 022 788PubChem CID 16747 1R 3R or trans33607 1S 3S or trans33606 1R 3S or cis20755 1S 3R or cisUNII 23FP207VLY 1R 3R or trans Y75957WZ15Y 1S 3S or trans Y5P7V8620AM 1R 3S or cis YTFK3B71TRY 1S 3R or cis YCompTox Dashboard EPA DTXSID60883558InChI 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 s1Key XLOPRKKSAJMMEW JGVFFNPUSA NSMILES CC CC1C C1 C C C O O CPropertiesChemical formula C 10H 16O 2Molar mass 168 236 g mol 1Melting point 17 C 63 F 290 K 1R 3R or transExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesBiosynthesis editChrysanthemic acid is derived from its pyrophosphate ester which in turn is produced naturally from two molecules of dimethylallyl diphosphate 3 nbsp Industrial synthesis editChrysanthemic 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 4 nbsp Many pyrethroids are accessible by re esterification of chrysanthemic acid ethylester References edit Faust Rudiger 2001 Fascinating Natural and Artificial Cyclopropane Architectures Angewandte Chemie International Edition 40 12 2251 2253 doi 10 1002 1521 3773 20010618 40 12 lt 2251 AID ANIE2251 gt 3 0 CO 2 R PMID 11433485 H Staudinger L Ruzicka Insektentotende Stoffe H Zur Konstitution der Chrysanthemummonocarbonsiiure und dicarbonsiiure Helv Chem Acta 7 1924 201 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 Bibcode 2001PNAS 98 4373R doi 10 1073 pnas 071543598 PMC 31842 PMID 11287653 Kelly Lawrence F 1987 A synthesis of chrysanthemic ester An undergraduate experiment J Chem Educ 64 12 1061 Bibcode 1987JChEd 64 1061K doi 10 1021 ed064p1061 Retrieved from https en wikipedia org w index php title Chrysanthemic acid amp oldid 1089206948, wikipedia, wiki, book, books, library,
