705-16-8

Basic information

• Product Name: trans-(±)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid
• Synonyms: trans-(±)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid;rel-3,3-Dimethyl-2β*-(2-methyl-1-propenyl)-1α*-cyclopropanecarboxylic acid;dl-trans-Form;XLOPRKKSAJMMEW-JGVFFNPUSA-N
• CAS NO: 705-16-8
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23284
• EINECS: 211-883-9
• Mol File: 705-16-8.mol
• Article Data: 13

Chemical Properties

• Melting Point: 54°
• Boiling Point: 85-90 °C(Press: 0.3 Torr)
• Appearance: /
• Density: 1.077±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly)
• PKA: 4.90±0.33(Predicted)
• CAS DataBase Reference: trans-(±)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: trans-(±)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid(705-16-8)
• EPA Substance Registry System: trans-(±)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid(705-16-8)

Safety Data

• Hazardous Substances Data: 705-16-8(Hazardous Substances Data)

Usage

Uses

(±)-trans-Chrysanthemic Acid is an related compound of natural and synthetic insecticides such as pyrethroids. Chrysanthemic acid is also found naturally occurring in seeds of Chrysanthemum.

InChI:InChI=1/C10H16O2/c1-6(2)5-7-8(9(11)12)10(7,3)4/h5,7-8H,1-4H3,(H,11,12)

Upstream product

• 97-41-6 ethyl trans-(+/-)-chrysanthemate 
• 97-41-6 ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate 
• 702-50-1 2,2,5,5-tetramethylcyclohexa-1,3-dione 
• 13855-90-8 2,2,5,5-tetramethylcyclohex-3-en-1-one 
• 78779-89-2 (+/-)-trans-2,2-dimethyl-3-(2',2'-dimethylvinyl)cyclopropanecarboxamide 
• 2198-88-1 (+/-)-cis-2,2-dimethyl-3-(2',2'-dimethylvinyl)cyclopropanecarbonitrile 
• 764-13-6 2,5-Dimethyl-2,4-hexadiene 
• 627-58-7 2,5-dimethyl-1,5-hexadiene 
• 142-30-3 2,5-dihydroxy-2,5-dimethyl-3-hexyne 
• 75646-37-6 Acetic acid (Z)-4-hydroxy-1,1,4-trimethyl-pent-2-enyl ester 
• 75996-50-8 (E)-6-Acetoxy-2-benzenesulfonyl-3,3,6-trimethyl-hept-4-enoic acid methyl ester 
• 76013-17-7 (E)-2-Benzenesulfonyl-6-hydroxy-3,3,6-trimethyl-hept-4-enoic acid methyl ester 
• 75996-53-1 Benzoic acid (E)-5-methoxycarbonyl-1,1,4,4-tetramethyl-pent-2-enyl ester 
• 75996-49-5 2-((E)-4-Hydroxy-1,1,4-trimethyl-pent-2-enyl)-malonic acid dimethyl ester 

Downstream Products

• 5460-63-9 methyl (dl)-trans-chrysanthemate 
• 97-41-6 ethyl trans-(+/-)-chrysanthemate 
• 2259-14-5 (1S,3S)-trans-chrysanthemic acid 
• 4638-92-0 (1R,3R)-trans-chrysanthemic acid 
• 454-25-1 (+/-)-trans-Homochrysanthemsaeure 
• 497-96-1 (+/-)-trans-(E)-pyrethricsaeure 
• 94672-92-1 (+/-)-2.2-dimethyl-3t-(2-methyl-propenyl)-cyclopropane-carbanilide-(1r) 
• 18228-69-8 rac-trans-1-(-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl)ethanone 
• 2861-25-8 trans-chrysanthemyl alcohol 
• 25402-06-6 (S)-3-((Z)-but-2-en-1-yl)-2-methyl-4-oxocyclopent-2-en-1-yl(1R,3R) -2,2-dimethyl-3-(2-methylprop-1-en-1-yl ) -cyclopropane-1-carboxylate 
• 121-21-1 pyrethrin I 
• 121-20-0 cinerin II 
• 1172-63-0 jasmolin II 
• 121-29-9 Pyrethrin II 

Relevant articles and documents

Total Syntheses of All Six Chiral Natural Pyrethrins: Accurate Determination of the Physical Properties, Their Insecticidal Activities, and Evaluation of Synthetic Methods

Chiral total syntheses of all six insecticidal natural pyrethrins (three pyrethrin I and three pyrethrin II compounds) contained in the chrysanthemum (pyrethrum) flower were performed. Three common alcohol components [(S)-cinerolone, (S)-jasmololone, and (S)-pyrethrolone] were synthesized: (i) straightforward Sonogashira-type cross-couplings using available (S)-4-hydroxy-3-methyl-2-(2-propynyl)cyclopent-2-en-1-ones (the prallethrin alcohol) for (S)-cinerolone (overall 52% yield, 98% ee) and (S)-pyrethrolone (overall 54% yield, 98% ee) and (ii) traditional decarboxylative-aldol condensation and lipase-catalyzed optical resolution for (S)-jasmololone (overall 16% yield, 96% ee). Two counter acid segments [(1R,3R)-chrysanthemic acid (A) and (1R,3R)-second chrysanthemic acid precursor (B)] were prepared: (i) C(1) epimerization of ethyl (±)-chrysanthemates and optical resolution using (S)-naphthylethylamine to afford A (96% ee) and (ii) concise derivatization of A to B (96% ee). All six pyrethrin esters (cinerin I/II, jasmolin I/II, and pyrethrin I/II) were successfully synthesized utilizing an accessible esterification reagent (TsCl/N-methylimidazole). To investigate the stereostructure-activity relationship, all four chiral stereoisomers of cinerin I were synthesized. Three alternative syntheses of (±)-jasmololone were investigated (methods utilizing Piancatelli rearrangement, furan transformation, and 1-nitropropene transformation). Insecticidal activity assay (KD50 and IC50) against the common mosquito (Culex pipiens pallens) revealed that (i) pyrethrin I > pyrethrin II, (ii) pyrethrin I (II) > cinerin I (II) ? jasmolin I (II), and (iii) "natural" cinerin I ? three "unnatural" cinerin I compounds (apparent chiral discrimination).

Syntheses of racemic and scalemic cis-chrysanthemic acid from β,γ-unsaturated cyclohexanol

2,2,5,5-Tetramethylcyclohexane-1,3-dione is a valuable starting-material precursor of cis-chrysanthemic acid. The (1S)-stereoisomer is a precursor of pyrethrin I, the most active natural insecticide from Chrysanthemum cinerariifolium, whereas the (1R)-stereoisomer is efficiently transformed to deltamethrin, the most active commercially available pyrethroid insecticide. Several intermediates have been identified and used with variable success for that purpose.

A practical method for O-acylation of N -hydroxythiazole-2(3 H)-thiones

O-Acylation of 4- and 4,5-substituted N-hydroxythiazole-2(3H)-thiones occurred in solutions of acetone upon treatment with solid K2CO3 and a variety of neat acyl chlorides (primary, secondary, and tertiary alkyl, aryl; 60-87% yield; ～10 g scale).