Cinerins

Title: Cinerins
Literature References: Active insecticidal constiutents of pyrethrum flowers. Isoln: Ward, Chem. Ind. (London) 1953, 586; Stephenson, Pyrethrum Post 5, no. 4, 22 (1960); C.A. 55, 13753g (1961). Structure: Schechter et al., J. Am. Chem. Soc. 71, 3165 (1949); Godin et al., J. Chem. Soc. C 1966, 332. Stereochemistry: Begley et al., Chem. Commun. 1972, 1276. Review: Crombie, Elliott, Fortschr. Chem. Org. Naturst. 19, 120-164 (1961). Review of toxicology and human exposure: Toxicological Profile for Pyrethrins and Pyrethroids (PB2004-100004, 2003) 332 pp.
Derivative Type: Cinerin I
CAS Registry Number: 25402-06-6
CAS Name: (1R,3R)-2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid (1S)-3-(2Z)-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl-ester
Molecular Formula: C20H28O3
Molecular Weight: 316.43
Percent Composition: C 75.91%, H 8.92%, O 15.17%
Properties: Viscous liquid. Oxidizes rapidly and becomes inactive in presence of air. bp0.008 136-138°. nD20 1.5064. [a]D20 -22° (hexane). uv max: 222 nm (e 21400). Practically insol in water. Sol in alcohol, petr ether, kerosene, carbon tetrachloride, ethylene dichloride, nitromethane.
Boiling point: bp0.008 136-138°
Optical Rotation: [a]D20 -22° (hexane)
Index of refraction: nD20 1.5064
Absorption maximum: uv max: 222 nm (e 21400)
Derivative Type: Cinerin II
CAS Registry Number: 121-20-0
CAS Name: (1R,3R)-3-[(1E)-3-Methoxy-2-methyl-3-oxo-1-propenyl]-2,2-dimethylcyclopropanecarboxylic acid (1S)-3-(2Z)-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester
Molecular Formula: C21H28O5
Molecular Weight: 360.44
Percent Composition: C 69.98%, H 7.83%, O 22.19%
Properties: Viscous liquid. Oxidizes rapidly and becomes inactive in presence of air. bp0.001 182-184°. nD20 1.5183. [a]D16 +16° (isooctane). uv max: 229 nm (e 28700). Practically insol in water. Sol in alcohol, petr ether (less sol than Cinerin I), kerosene, carbon tetrachoride, ethylene dichloride, nitromethane.
Boiling point: bp0.001 182-184°
Optical Rotation: [a]D16 +16° (isooctane)
Index of refraction: nD20 1.5183
Absorption maximum: uv max: 229 nm (e 28700)
CAUTION: Direct skin contact and inhalation may cause allergic attacks in sensitive people. Potential symptoms of overexposure are severe dermatitis, asthma, vasomotor rhinitis, anaphylactic reactions; numbness of lips and tongue, sneezing, vomiting, diarrhea; headache, restlessness, tinnitis, incoordination, clonic convulsions, stupor, prostration; death due to respiratory paralysis. See: Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section III, pp 352-355.
Use: Insecticide.
Cinidon-ethyl Cinitapride Cinmetacin Cinmethylin Cinnabarine