Chrysanthemic acid

Chrysanthemic acid
Names
	IUPAC name 2,2-Dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylic acid
Identifiers
CAS Number	4638-92-0 (1R,3R) or (+)-trans ; 2259-14-5 (1S,3S) or (−)-trans ; 26771-11-9 (1R,3S) or (+)-cis ; 26771-06-2 (1S,3R) or (−)-cis ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1437285;
ChemSpider	15876 (+)-trans; 19543 (−)-cis;
ECHA InfoCard	100.022.788
PubChem CID	16747 (1R,3R) or (+)-trans; 33607 (1S,3S) or (−)-trans; 33606 (1R,3S) or (+)-cis; 20755 (1S,3R) or (−)-cis;
UNII	23FP207VLY (1R,3R) or (+)-trans ; 75957WZ15Y (1S,3S) or (−)-trans ; 5P7V8620AM (1R,3S) or (+)-cis ; TFK3B71TRY (1S,3R) or (−)-cis ;
CompTox Dashboard (EPA)	DTXSID101033188 DTXSID60883558, DTXSID101033188 ;
	InChI 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;
	SMILES CC(=CC1C(C1(C)C)C(=O)O)C;
Properties
Chemical formula	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). Infobox references

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]

Biosynthesis

Chrysanthemic acid is derived from its pyrophosphate ester, which in turn is produced naturally from two molecules of dimethylallyl diphosphate.^[3]

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:^[4]

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

References

^ 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. 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.

[1] 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.

[staudinger24-2] H. Staudinger, L. Ružička: "Insektentotende Stoffe H. Zur Konstitution der Chrysanthemummonocarbonsiiure und -dicarbonsiiure", Helv. Chem. Acta 7 (1924) 201

[3] 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.

[4] 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.

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