Product Name

  • Name

    PYRETHRIN 1

  • EINECS
  • CAS No. 121-21-1
  • Article Data8
  • CAS DataBase
  • Density 1.04g/cm3
  • Solubility
  • Melting Point
  • Formula C21H28 O3
  • Boiling Point 424.3°Cat760mmHg
  • Molecular Weight 328.452
  • Flash Point 182.3°C
  • Transport Information
  • Appearance
  • Safety Poison by ingestion and intravenous routes. When heated to decomposition it emits acrid smoke and irritating fumes. An insecticide. See also PYRETHRIN; PYRETHRIN II; PYRETHRINS.
  • Risk Codes 20/21/22-50/53
  • Molecular Structure Molecular Structure of 121-21-1 (PYRETHRIN 1)
  • Hazard Symbols
  • 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
  • PSA 43.37000
  • LogP 4.55820

Synthetic route

(1R,3R)-trans-chrysanthemic acid
4638-92-0

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

(S)-(+)-pyrethrolone
487-67-2

(S)-(+)-pyrethrolone

pyrethrin I
121-21-1

pyrethrin I

Conditions
ConditionsYield
Stage #1: (1R,3R)-trans-chrysanthemic acid With 1-methyl-1H-imidazole; p-toluenesulfonyl chloride In acetonitrile at 0 - 5℃; for 0.5h; Inert atmosphere;
Stage #2: (S)-(+)-pyrethrolone In acetonitrile at 20 - 25℃; for 2h; Inert atmosphere;		74%
acyl chloride of (1R)-2.2-dimethyl-3t-<2-methyl-propenyl>-cyclopropane-carboxylic acid-(1r)

acyl chloride of (1R)-2.2-dimethyl-3t-<2-methyl-propenyl>-cyclopropane-carboxylic acid-(1r)

(S)-5-hydroxy-1-methyl-2-c.4)-yl>-cyclopenten-(1)-one-(3)

(S)-5-hydroxy-1-methyl-2-c.4)-yl>-cyclopenten-(1)-one-(3)

pyrethrin I
121-21-1

pyrethrin I

Conditions
ConditionsYield
With pyridine; benzene
chrysanthemoyl CoA

chrysanthemoyl CoA

(S)-(+)-pyrethrolone
487-67-2

(S)-(+)-pyrethrolone

pyrethrin I
121-21-1

pyrethrin I

Conditions
ConditionsYield
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; Kinetics; Reagent/catalyst; Enzymatic reaction;
(1R,3R)-trans-chrysanthemic acid
4638-92-0

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

pyrethrin I
121-21-1

pyrethrin I

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride / 0.5 h / 50 - 100 °C
2: 1 h / 0 °C / Reflux
3: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0 °C
View Scheme
(1R)-trans-3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride
4489-14-9

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

C11H15IO2

C11H15IO2

pyrethrin I
121-21-1

pyrethrin I

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1 h / 0 °C / Reflux
2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0 °C
View Scheme
C21H29IO3

C21H29IO3

pyrethrin I
121-21-1

pyrethrin I

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 0℃;
(S)-4-hydroxy-3-methyl-2-(2-propenyl)-2-cyclopenten-1-one
22373-75-7

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

pyrethrin I
121-21-1

pyrethrin I

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: [2-(1-methylethoxy-O)phenylmethyl-C](nitrato-O,O'){rel-(2R,5R,7R)-adamantane-2,1-diyl[3-(2,4,6-trimethylphenyl)-1-imidazolidinyl-2-ylidene]}ruthenium / tetrahydrofuran / 12 h / 35 °C
2: 1 h / 0 °C / Reflux
3: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0 °C
View Scheme
(S)-(+)-4-hydroxy-3-methyl-2-(pent-4-en-2-ynyl)-2-cyclopenten-1-one

(S)-(+)-4-hydroxy-3-methyl-2-(pent-4-en-2-ynyl)-2-cyclopenten-1-one

pyrethrin I
121-21-1

pyrethrin I

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogenchloride; zinc / ethanol; water / 16 h / 75 - 80 °C / Inert atmosphere
2.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere
2.2: 2 h / 20 - 25 °C / Inert atmosphere
View Scheme
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

ethyl trans-(+/-)-chrysanthemate

pyrethrin I
121-21-1

pyrethrin I

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium hydroxide / ethanol; water / 3 h
2.1: (S)-1-(1-Naphthyl)ethylamine / ethanol / 3 h / 20 °C
3.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere
3.2: 2 h / 20 - 25 °C / Inert atmosphere
View Scheme
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

trans-chrysanthemic acid

pyrethrin I
121-21-1

pyrethrin I

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: (S)-1-(1-Naphthyl)ethylamine / ethanol / 3 h / 20 °C
2.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere
2.2: 2 h / 20 - 25 °C / Inert atmosphere
View Scheme
(S)-4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-one
77087-34-4

(S)-4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-one

pyrethrin I
121-21-1

pyrethrin I

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / toluene / 16 h / 20 - 25 °C / Inert atmosphere
2.1: hydrogenchloride; zinc / ethanol; water / 16 h / 75 - 80 °C / Inert atmosphere
3.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere
3.2: 2 h / 20 - 25 °C / Inert atmosphere
View Scheme
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

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

pyrethrin I
121-21-1

pyrethrin I

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydride / mineral oil / 3 h / Inert atmosphere
2.1: potassium hydroxide / ethanol; water / 3 h
3.1: (S)-1-(1-Naphthyl)ethylamine / ethanol / 3 h / 20 °C
4.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere
4.2: 2 h / 20 - 25 °C / Inert atmosphere
View Scheme
pyrethrin I
121-21-1

pyrethrin I

(1S)-2-methyl-4-oxo-3-pentylcyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

(1S)-2-methyl-4-oxo-3-pentylcyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 20℃; for 4h;83%
pyrethrin I
121-21-1

pyrethrin I

(1S,4R)-4-hydroxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

(1S,4R)-4-hydroxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

Conditions
ConditionsYield
With L-Selectride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; stereoselective reaction;38%
pyrethrin I
121-21-1

pyrethrin I

A

(S)-2-methyl-4-oxo-3-(penta-1,3-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

(S)-2-methyl-4-oxo-3-(penta-1,3-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

B

(1S)-2-methyl-4-oxo-3-((E)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

(1S)-2-methyl-4-oxo-3-((E)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

Conditions
ConditionsYield
With formic acid; palladium 10% on activated carbon In tetrahydrofuran for 5h; Inert atmosphere; Reflux;A 15%
B 9%
pyrethrin I
121-21-1

pyrethrin I

acetic acid
64-19-7

acetic acid

A

(1S,4S)-4-acetoxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

(1S,4S)-4-acetoxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

B

(1S,4R)-4-hydroxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

(1S,4R)-4-hydroxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

C

(1S,4R)-4-acetoxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

(1S,4R)-4-acetoxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

Conditions
ConditionsYield
Stage #1: pyrethrin I With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran for 5h; Inert atmosphere;
Stage #2: acetic acid In tetrahydrofuran for 1h; Inert atmosphere; Reflux;		A n/a
B 15%
C n/a
...Expand
pyrethrin I
121-21-1

pyrethrin I

(Ξ)-4-ethoxy-3-methyl-2-penta-2c,4-dienyl-cyclopent-2-enone-(2,4-dinitro-phenylhydrazone)
102161-17-1

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

Conditions
ConditionsYield
With ethanol; sulfuric acid; (2,4-dinitro-phenyl)-hydrazine
pyrethrin I
121-21-1

pyrethrin I

(1R,3R)-trans-chrysanthemic acid
4638-92-0

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

Conditions
ConditionsYield
With potassium hydroxide In ethanol Hydrolysis;
pyrethrin I
121-21-1

pyrethrin I

(1R)-2.2-dimethyl-3t-<2-methyl-propenyl>-cyclopropane-carboxylic acid-(1r)-<(S)-4-oxo-2-methyl-3-(pentadien-(1.3c)-yl-(t))-cyclopenten-(2)-yl ester

(1R)-2.2-dimethyl-3t-<2-methyl-propenyl>-cyclopropane-carboxylic acid-(1r)-<(S)-4-oxo-2-methyl-3-(pentadien-(1.3c)-yl-(t))-cyclopenten-(2)-yl ester

pyrethrin I
121-21-1

pyrethrin I

(1S,4S)-4-acetoxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

(1S,4S)-4-acetoxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / tetrahydrofuran; methanol / 3 h / 0 °C
2: triethylamine / dichloromethane / 4.5 h / Inert atmosphere; Reflux
View Scheme
pyrethrin I
121-21-1

pyrethrin I

A

(S)-2-methyl-4-oxo-3-((Z)-pent-2-en-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)-cyclopropane-1-carboxylate
4466-14-2

(S)-2-methyl-4-oxo-3-((Z)-pent-2-en-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)-cyclopropane-1-carboxylate

B

(1S)-2-methyl-4-oxo-3-pentylcyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

(1S)-2-methyl-4-oxo-3-pentylcyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; hydrazine hydrate; acetic acid In tetrahydrofuranA 68 %Chromat.
B 25 %Chromat.
pyrethrin I
121-21-1

pyrethrin I

A

(1S,4R)-4-hydroxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

(1S,4R)-4-hydroxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

B

(1S,4S)-4-hydroxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

(1S,4S)-4-hydroxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran; methanol at 0℃; for 3h;A 202 mg
B 45 mg
pyrethrin I
121-21-1

pyrethrin I

(1S,4R)-4-acetoxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

(1S,4R)-4-acetoxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 5 h / Inert atmosphere
1.2: 1 h / Inert atmosphere; Reflux
2.1: triethylamine / dichloromethane / 4.5 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / tetrahydrofuran; methanol / 3 h / 0 °C
2: triethylamine / dichloromethane / 4.5 h / Inert atmosphere; Reflux
View Scheme

PYRETHRIN I Chemical Properties

Molecular Formula: C21H28O3
Molecular Weight: 328.49
EINECS: 204-455-8
Density: 1.04g/cm3
Flash Point: 182.3°C
Storage temp: 0-6°C
Enthalpy of Vaporization: 67.88 kJ/mol 
Boiling Point: 424.3 °C at 760 mmHg 
Vapour Pressure: 2.09E-07 mmHg at 25°C 
Boiling Point of Pyrethrony l (121-21-1): 424.3°Cat760mmHg
IUPAC Name: [(1S)-2-methyl-4-oxo-3-[(2E)-penta-2,4-dienyl]cyclopent-
2-en-1-yl] (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-
1-carboxylate
Synonyms: Pyrethrony l ; (+)-Pyrethronyl(+)-trans-chrysanthemate ; 2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylicacid2-methyl-4-oxo ; 2,2-Dimethyl-3-(2-methylpropenyl)-cyclopropaneacrylicaciesterwith4-hydr ; 2,2-Dimethyl-3-(2-methylpropenyl)-cyclopropanecarboxylicaciesterwith4-h
Following is the molecular structure of Pyrethrony l (121-21-1):

PYRETHRIN I Toxicity Data With Reference

1.    

orl-rat LD50:260 mg/kg

     PCBPBS    Pesticide Biochemistry and Physiology. 2 (1972),308.
2.    

ivn-rat LDLo:5 mg/kg

     BIOGAL    Biologico. 41 (10)(1975),283.

PYRETHRIN I Safety Profile

Poison by ingestion and intravenous routes. When heated to decomposition it emits acrid smoke and irritating fumes. An insecticide.
Safety Information of Pyrethrony l (121-21-1):
Hazard Codes: Xn,N
Xn: Harmful N:Dangerous for the environment
Risk Statements: 20/21/22-50/53
20/21/22: Harmful by inhalation, in contact with skin and if swallowed 
50/53: Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment  
Safety Statements: 13-60-61
13: Keep away from food, drink and animal feeding stuffs 
60: This material and/or its container must be disposed of as hazardous waste 
61: Avoid release to the environment. Refer to special instructions safety data sheet  
RIDADR  2902
HazardClass: 6.1(b)
PackingGroup: III
 

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