Bioallethrin

Common name: bioallethrin; depalléthrine; d-trans-allethrin
IUPAC name: (RS)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (1R, 3R)-2, 2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate Alt: (RS)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (+)-trans-chrysanthemate
Roth: (RS)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (1R)-trans-2, 2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
Chemical Abstracts name: 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl 2, 2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate
CAS RN: [584-79-2] (same as for allethrin)
EEC no.: 209-542-4

PHYSICAL CHEMISTRY
Composition: Bioallethrin contains 93% m/m total isomers, of which there is 90% trans- isomer pair and 3% cis- isomer pair. Material in 'D-Trans' is 90% m/m bioallethrin. For d-allethrin, see allethrin [(1R)- isomers]. Mol. wt.: 302.4; M.f.: C19H26O3; Form: Bioallethrin is an orange-yellow viscous liquid. The material in 'D-Trans' is an amber viscous liquid. M.p.: Not applicable; no crystallisation observed at -40 ºC. B.p.: Bioallethrin 165-170 ºC/0.15 mmHg; V.p.: 43.9 mPa (25 ºC); KOW: logP = 4.68 (25 ºC); Henry: 2.89 Pa m3 mol-1 (calc.) S.g./density: 1.012 at 20 ºC; Solubility: Bioallethrin: in water 4.6 mg/l (25 ºC). Completely miscible with acetone, ethanol, chloroform, ethyl acetate, hexane, toluene and dichloromethane (20 ºC). Stability: Degraded by u.v. light. In aqueous solution, DT50 1410.7 d (pH 5), 547.3 d (pH 7), 4.3 d (pH 9). Specific rotation: [a]D20 -18.5 to -22.5 (50 g/l toluene); F.p.: 87 ºC (Pensky-Martens)