(-)-trans-Chrysanthemic acid

Base Information

• Chemical Name: (-)-trans-Chrysanthemic acid
• CAS No.: 2259-14-5
• Deprecated CAS: 22467-79-4,827-90-7
• Molecular Formula: C10H16 O2
• Molecular Weight: 168.236
• Hs Code.: 2916209090
• European Community (EC) Number: 247-996-5,211-883-9,218-858-1
• UNII: 360DB5209D,75957WZ15Y
• DSSTox Substance ID: DTXSID50883820,DTXSID60883558
• Nikkaji Number: J52.427A
• Wikidata: Q27118138
• Metabolomics Workbench ID: 56166
• Mol file: 2259-14-5.mol

Synonyms:2259-14-5;(-)-trans-Chrysanthemic acid;(1S,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylic acid;705-16-8;Chrysanthemic acid dl-trans-form;Chrysanthemic acid l-trans-;(1S-trans)-2,2-Dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid;EINECS 218-858-1;l-trans-chrysanthemic acid;BRN 1862973;(1S-trans)-2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid;(-)-trans-Chrysanthemumsaeure;UNII-360DB5209D;UNII-75957WZ15Y;EINECS 211-883-9;(1S,3S)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylic acid;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1S,3S)-;360DB5209D;75957WZ15Y;AI3-33937;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, (1S,3S)-;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1R,3R)-rel-;trans-2,2-Dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylic acid;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, (1R,3R)-rel-;CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYLPROPENYL)-, (1S-trans)-;4-09-00-00169 (Beilstein Handbook Reference);DL-trans-Chrysanthemumic acid;EINECS 225-067-5;BRN 2043419;NCIMech_000061;(?)-trans-Chrysanthemic acid;SCHEMBL1150597;(1R-cis)-2,2-Dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, trans-;(+/-)-trans-Chrysanthemic acid;CHEBI:39102;DTXSID50883820;DTXSID60883558;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1R-trans)-;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-,(1R,3S)-;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-,(1R-cis)-;CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYLPROPENYL)-, (1R,3S)-(+)-;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methylpropenyl)-,(1R,3R)-()-;CCG-35376;CHRYSANTHEMIC ACID, DL-TRANS-;TRANS-(-)-CHRYSANTHEMIC ACID;AKOS016008603;CHRYSANTHEMIC ACID L-TRANS-FORM;CHRYSANTHEMIC ACID, TRANS-(-)-;LS-58671;LS-58673;CHRYSANTHEMIC ACID, (+/-)-TRANS-;CHRYSANTHEMIC ACID, TRANS-(+/-)-;CHRYSANTHEMIC ACID L-TRANS-FORM [MI];CHRYSANTHEMIC ACID DL-TRANS-FORM [MI];A878499;Q27118138;(-)-trans-2,2-dimethyl-3-isobutenylcyclopropane-1-carboxylic acid;Trans-(+-)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid;trans-(1)-2,2-Dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid;(1S,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylic acid;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1S-trans)-;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, trans-(.+.)-;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-,(1S,3S)-;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methylpropenyl)-,(1S,3S)-(-)-;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methylpropenyl)-,trans-(.+.)-

Chemical Property of (-)-trans-Chrysanthemic acid

Chemical Property:

• Melting Point: 17-21°
• Boiling Point: 246.4°Cat760mmHg
• Flash Point: 119°C
• PSA: 37.30000
• Density: 1.077g/cm³
• LogP: 2.30940
• Storage Temp.: 2-8°C
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 168.115029749
• Heavy Atom Count: 12
• Complexity: 234

Purity/Quality:

99% ^*data from raw suppliers

(1S,3S)-2,2-Dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC1C(C1(C)C)C(=O)O)C
• Isomeric SMILES: CC(=C[C@H]1[C@@H](C1(C)C)C(=O)O)C

Technology Process of (-)-trans-Chrysanthemic acid

There total 73 articles about (-)-trans-Chrysanthemic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

ethyl trans-(+/-)-chrysanthemate (97-41-6,1802-02-4,7377-84-6,15543-65-4,16642-27-6,34909-55-2,41641-25-2,41641-26-3,41641-27-4) → trans-chrysanthemic acid (827-90-7,2259-14-5,2935-23-1,4638-92-0,10453-89-1,15259-78-6,26771-06-2,26771-11-9,705-16-8)

Guidance literature:

With potassium hydroxide; In ethanol; water; for 3h;

DOI:10.1021/acs.joc.9b02767

Reference yield: 73.0%

tert-amyl trans-chrysanthemate (78715-54-5) → trans-chrysanthemic acid (827-90-7,2259-14-5,2935-23-1,4638-92-0,10453-89-1,15259-78-6,26771-06-2,26771-11-9,705-16-8)

Guidance literature:

With potassium hydroxide; In ethanol; for 24h; Heating;

DOI:10.1021/jo00335a002

Reference yield: 63.0%

N-[trans-2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarbonyloxy]-5-(4-methoxyphenyl)-4-methylthiazole-2(3H)-thione → trans-chrysanthemic acid (827-90-7,2259-14-5,2935-23-1,4638-92-0,10453-89-1,15259-78-6,26771-06-2,26771-11-9,705-16-8)

Guidance literature:

With cyclohexa-1,4-diene; In benzene; at 20 ℃; for 7.5h; Photolysis;

DOI:10.1055/s-0029-1217102

upstream raw materials:

trans-chrysanthemic acid

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

chrysanthemumic acid methyl ester

methyl (dl)-trans-chrysanthemate

Downstream raw materials:

(1R,3R)-trans-chrysanthemic acid

(+/-)-trans-Homochrysanthemsaeure

(+/-)-trans-(E)-pyrethricsaeure

(+/-)-2.2-dimethyl-3t-(2-methyl-propenyl)-cyclopropane-carbanilide-(1r)

Refernces

• 1、 Matsumoto et al.. "". . p. 481. Retrieved 1963.
• 2、 Nanda,Bhaskar Rao,Yadav. "Enzyme catalysed kinetic resolution of racemic 2,2-dimethyl-3-(2,2- disubstituted vinyl) cyclopropane carboxylic acids anchored on polymer supports". . p. 5905 - 5908. Retrieved 1999.
• 3、 Tappin, Nicholas D. C.,Michalska, Weronika,Rohrbach, Simon,Renaud, Philippe. "Cyclopropanation of Terminal Alkenes through Sequential Atom-Transfer Radical Addition/1,3-Elimination". supporting information. p. 14240 - 14244. Retrieved 2019/08/26.
• 4、 Krief, Alain,Jeanmart, Stéphane,Gondal, Humaira Y.,Kremer, Adrian. "Syntheses of racemic and scalemic cis-chrysanthemic acid from β,γ-unsaturated cyclohexanol". . p. 2123 - 2167. Retrieved 2013/02/23.