PYRETHRIN 1

Base Information

• Chemical Name: PYRETHRIN 1
• CAS No.: 121-21-1
• Molecular Formula: C21H28 O3
• Molecular Weight: 328.452
• Hs Code.: 29183000
• Mol file: 121-21-1.mol

Synonyms:Cyclopropanecarboxylicacid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-,(1S)-2-methyl-4-oxo-3-(2Z)-2,4-pentadienyl-2-cyclopenten-1-yl ester, (1R,3R)-(9CI); Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-,2-methyl-4-oxo-3-(2,4-pentadienyl)-2-cyclopenten-1-yl ester, [1R-[1a[S*(Z)],3b]]-; Cyclopropanecarboxylic acid,2,2-dimethyl-3-(2-methylpropenyl)-, ester with4-hydroxy-3-methyl-2-(2,4-pentadienyl)-2-cyclopenten-1-one (8CI); Pyrethrin 1(6CI); (+)-Pyrethronyl (+)-trans-chrysanthemate; Chrysanthemummonocarboxylicacid pyrethrolone ester; Pyrethrin I

Chemical Property of PYRETHRIN 1

Chemical Property:

• Vapor Pressure: 2.09E-07mmHg at 25°C
• Refractive Index: nD20 1.5242
• Boiling Point: 424.3°Cat760mmHg
• Flash Point: 182.3°C
• PSA: 43.37000
• Density: 1.04g/cm³
• LogP: 4.55820
• Storage Temp.: 0-6°C

Purity/Quality:

99.9% ^*data from raw suppliers

Pyrethrin1 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,N
• Statements: 20/21/22-50/53
• Safety Statements: 13-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Technology Process of PYRETHRIN 1

There total 19 articles about PYRETHRIN 1 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: 74.0%

(1R,3R)-trans-chrysanthemic acid (4638-92-0) + (S)-(+)-pyrethrolone (487-67-2) → pyrethrin I (121-21-1)

Guidance literature:

(1R,3R)-trans-chrysanthemic acid; With 1-methyl-1H-imidazole; p-toluenesulfonyl chloride; In acetonitrile; at 0 - 5 ℃; for 0.5h; Inert atmosphere;

(S)-(+)-pyrethrolone; In acetonitrile; at 20 - 25 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.joc.9b02767

Reference yield:

C21H29IO3 → pyrethrin I (121-21-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 ℃;

Reference yield:

chrysanthemoyl CoA + (S)-(+)-pyrethrolone (487-67-2) → pyrethrin I (121-21-1)

Guidance literature:

With (maltose-binding protein)-fusedTanacetum cinerariifolium GDSL lipase/esterase,recombinant, molecular weight: 81689 Da; In aq. buffer; at 25 ℃; for 0.166667h; pH=7.5; Reagent/catalyst; Kinetics; Enzymatic reaction;

DOI:10.1271/bbb.130143

upstream raw materials:

(S)-(+)-pyrethrolone

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

(1R)-trans-3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride

(S)-4-hydroxy-3-methyl-2-(2-propenyl)-2-cyclopenten-1-one

Downstream raw materials:

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

(Ξ)-4-ethoxy-3-methyl-2-penta-2c,4-dienyl-cyclopent-2-enone-(2,4-dinitro-phenylhydrazone)

Refernces

• 1、 Ashida, Yuichiro,Kawamoto, Momoyo,Matsuo, Noritada,Moriyama, Mizuki,Tanabe, Yoo. "Total Syntheses of All Six Chiral Natural Pyrethrins: Accurate Determination of the Physical Properties, Their Insecticidal Activities, and Evaluation of Synthetic Methods". . p. 2984 - 2999. Retrieved 2020/03/24.
• 2、 Sasaki,Okada,Matsui. "A convenient conversion of allethrolone into pyrethrolone". . p. 379 - 381. Retrieved 2007/10/13.