15259-78-6

Basic information

• Product Name: cis-chrysanthemic acid
• Synonyms: cis-chrysanthemic acid;cis-Chrysanthemum monocarboxylic acid;cis-Chrysanthemumic acid;cis-Chrysanthemum-monocarboxylic acid;rel-(1R*)-2,2-Dimethyl-3β*-(2-methyl-1-propenyl)cyclopropane-1β*-carboxylic acid;rel-2α*-(2-Methyl-1-propenyl)-3,3-dimethylcyclopropane-1α*-carboxylic acid
• CAS NO: 15259-78-6
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 0
• EINECS: 220-908-2
• Mol File: 15259-78-6.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 246.4°C at 760 mmHg
• Flash Point: 119°C
• Appearance: /
• Density: 1.077g/cm³
• Vapor Pressure: 0.0088mmHg at 25°C
• Refractive Index: 1.546
• CAS DataBase Reference: cis-chrysanthemic acid(CAS DataBase Reference)
• NIST Chemistry Reference: cis-chrysanthemic acid(15259-78-6)
• EPA Substance Registry System: cis-chrysanthemic acid(15259-78-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-42/43
• Safety Statements: 26-36
• Hazardous Substances Data: 15259-78-6(Hazardous Substances Data)

Usage

Uses

cis-Chrysanthemic Acid is an intermediate in synthesizing (+)-cis-Phenothrin (P318100), an isomer of Phenothrin (P318095), which is a pesticide used in the control of pests and insects.

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)/t7-,8-/m0/s1

Upstream product

• 5460-63-9 methyl (dl)-trans-chrysanthemate 
• 764-13-6 2,5-Dimethyl-2,4-hexadiene 
• 76-02-8 trifluoroacetyl chloride 
• 97-41-6 ethyl trans-(+/-)-chrysanthemate 
• 97-41-6 ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate 
• 19165-55-0 2,2,5,5-tetramethylcyclohex-3-en-1-ol 
• 15500-76-2 Dimethyl-dimedon-mono-(toluol-4-sulfonyl-hydrazon) 
• 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 
• 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 

Downstream Products

• 5460-63-9 methyl (dl)-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) 
• 94672-92-1 (1S)-2.2-dimethyl-3t-(2-methyl-propenyl)-cyclopropane-carbanilide-(1r) 
• 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 
• 93132-69-5 (1R,3R)-2,2-Dimethyl-3-((E)-2-methyl-3-oxoprop-1-en-1-yl)cyclopropane-1-carboxylic Acid 
• 1189-99-7 2,5,5-Trimethyl-heptan 

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.

Unprecedented dual reactivity of anhydrous potassium hydroxide in cascade cyclopropannelation/Haller-Bauer-scission/Grob-fragmentation reactions

We report an unprecedented type of reactivity of 'anhydrous potassium hydroxide' ('APH') in which it plays, over a large variety of related educts, sequentially the role of base and nucleophile. Some insight into the structure of reactive species as well as comparative reactivity of related reagents prepared by fusion of commercially available potassium hydroxide or by adding stoichiometric amount of water to potassium hydride is provided.