Chrysanthemic acid

Chrysanthemic acid
IUPAC name 2,2-Dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylic acid
Identifiers
CAS number	4638-92-0 (1R,3R) or (+)-trans
PubChem	16747 (1R,3R) or (+)-trans, 33607 (1S,3S) or (-)-trans, 33606 (1R,3S) or (+)-cis, 20755 (1S,3R) or (-)-cis
ChemSpider	15876 (+)-trans, 19543 (-)-cis
Jmol-3D images	Image 1
SMILES CC(=CC1C(C1(C)C)C(=O)O)C
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
Properties
Molecular formula	C10H16O2
Molar mass	168.23 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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-derived group of 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.

Biosynthesis

Chrysanthemic acid is derived from its pyrophosphate ester, which in turn is produced naturally from dimethylallyl diphosphate.^[1]

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^[2]:

Many pyrethroids are accessible by re-esterification of crysanthemic acid ethylester.

References

1. ^ 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. doi:10.1073/pnas.071543598. PMC 31842. PMID 11287653. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=31842. 
2. ^ A synthesis of chrysanthemic ester: An undergraduate experiment. Kelly, Lawrence F. J. Chem. Educ. 1987, 64, 1061.

This article about an organic compound is a stub. You can help Wikipedia by expanding it.v · Categories: Organic compound stubs Carboxylic acids Monoterpenes Cyclopropanes Wikimedia Foundation. 2010. Игры ⚽ Нужно решить контрольную? Chrysanthellum Chrysanthemin Look at other dictionaries: Organophosphate — General chemical structure of an organophosphate An organophosphate (sometimes abbreviated OP) is the general name for esters of phosphoric acid. Phosphates are probably the most pervasive organophosphorus compounds. Many of the most important… …   Wikipedia Parathion — IUPAC name O,O Diethyl O (4 nitrophenyl) phosphorothioate …   Wikipedia Pesticide — A cropduster spraying pesticide on a field Pesticides are substances or mixture of substances intended for preventing, destroying, repelling or mitigating any pest.[1] A pesticide may be a chemical unicycle, biological agent (such as a virus or… …   Wikipedia Pyrethroid — A pyrethroid is a synthetic chemical compound similar to the natural chemical pyrethrins produced by the flowers of pyrethrums ( Chrysanthemum cinerariaefolium and C. coccineum ). Pyrethroids are common in commercial products such as household… …   Wikipedia Malathion — Malathion …   Wikipedia Imidacloprid — Imidacloprid[1] …   Wikipedia Chlorfenvinphos — IUPAC name [(EZ) 2 Chloro 1 (2,4 dichlorophenyl)ethenyl] diethyl phosphate …   Wikipedia Diazinon — IUPAC name O,O Diethyl O [4 methyl 6 (propan 2 yl)pyrimidin 2 yl] phosphorothioate …   Wikipedia Dimethoate — IUPAC name O,O dimethyl S [2 (methylamino) 2 oxoethyl] dithiophosphate …   Wikipedia Omethoate — IUPAC name 2 [(Dimethoxyphosphoryl)sulfanyl] N methyl acetamide …   Wikipedia 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”