| Identification | More | [Name]
Empenthrin | [CAS]
54406-48-3 | [Synonyms]
1-ETHINYL-2-METHYL-2-PENTEN-1-YL CHRYSANTHEMATE
D-EMPENTHRIN
[(E)-4-methylhept-4-en-1-yn-3-yl] 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
EMPENTHRIN
VAPORTHRIN
(rs)-(e)-1-ethynyl-2-methyl-2-pentenyl(1r)-cis,trans-chrysanthemate
2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropanecarboxylicaci1-ethynyl-2
2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropanecarboxylicaci1-ethynyl-2-methyl-2-pentenylester
Cyclopropanecarboxylicacid,2,2-dimethyl-3-(2-methyl-1-propenyl)-,1-ethynyl-2-methyl-2-pentenylester
empenthrin[(1r)isomers]
ma108
-methyl-2-pentenylester
s2852
s2852f
s2852forte
1-ethynyl-2-methylpent-2-enyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
Empenthrin, Pestanal
(E)-1-Ethynyl-2-methylpenten-2-yl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate
Chrysanthemic acid, (E)-1-ethynyl-2-methylpenten-2-yl ester
empenthrin (bsi, draft e-iso) | [EINECS(EC#)]
259-154-4 | [Molecular Formula]
C18H25O2- | [MDL Number]
MFCD01745518 | [Molecular Weight]
273.39 | [MOL File]
54406-48-3.mol |
| Chemical Properties | Back Directory | [Appearance]
liquid | [Melting point ]
25°C | [Boiling point ]
377.38°C (rough estimate) | [density ]
0.9965 (rough estimate) | [vapor pressure ]
1.4×10-2 Pa (23.6 °C) | [refractive index ]
1.5510 (estimate) | [storage temp. ]
2-8°C | [Water Solubility ]
0.11 mg l-1 (25 °C) | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [Henry's Law Constant]
2.9×10-2 mol/(m3Pa) at 25℃, Ebert et al. (2023) | [CAS DataBase Reference]
54406-48-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn;N,N,Xn | [Risk Statements ]
R22:Harmful if swallowed.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 3082 | [RTECS ]
GZ1728000 | [HS Code ]
29162090 |
| Hazard Information | Back Directory | [Description]
Empenthrin, also known as vaporthrin, (2E)-1-ethynyl-2-methyl-2-penten-1-yl 2,2-
dimethyl-3-(2-methyl-1-propen-1-yl) cyclopropanecarboxylate, is a derivative of 1-ethynyl-
2-methyl penten-2-ol. The vapor pressure of empenthrin at room temperature is suitable and therefore
it has a natural volatility. At 30 °C, the vapor pressures of empenthrin and allethrin
are 1.62×103 and 1.20×104 mmHg, respectively. Thus, the vapor pressure of empenthrin is about 10 times more than that of allethrin. Moreover, empenthrin is odorless.
It has strong killing activity and repellent effect on pests and is very suitable for textile
mothproofing. | [Chemical Properties]
liquid | [Uses]
Empenthrin is an insecticidal pyrethroid compound. | [Uses]
Empenthrin is used as a domestic insecticide, especially against
moths and other insects which attack fabrics. | [Definition]
ChEBI:Empenthrin is a monoterpenoid. | [Preparation]
About 3.72 g (0.03 mol) of 2-methyl-1-ethynyl-2-pentenol and 3.16 g (0.04 mol) of pyridine were added to toluene to form a solution. A toluene solution containing 5.6 g
(0.03 mol) of Chrysanthemoyl chloride was added in a dropwise manner. The reaction was carried out at a temperature of 40–50°C for 6h. After reaction, the reaction
solution was washed with water until neutral, dried and then subjected to distillation
under reduced pressure. About 5.7 g of empenthrin was collected from a fraction of
120–126°C (0.03 mmHg). The yield of empenthrin was 69%. | [Mechanism of action]
Contact action. Sodium channel modulator. | [Metabolic pathway]
Empenthrin is a low molecular weight ester of (1R)-chrysanthemic acid
(2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid). It
has a relatively high vapour pressure and, unlike most pyrethroids, it is
effective against flying insects. The molecule has three chiral centres and
geometric isomerism in the alcohol group but, with the exception of the
1R acid, the full isomer mixture is used. As the insecticide has been
developed for domestic use, it is unlikely that there will be a requirement
for metabolism studies in plants or for extensive environmental fate studies.
Its metabolism in rats has been reported, with particular attention
paid to the fate of the novel alcohol moiety. As with other pyrethroids,
ester cleavage and oxidation and conjugation of the alcohol metabolite
predominated. The fate of the chrysanthemic acids can be assessed by
reference to phenothrin. | [Degradation]
Empenthrin is a stable molecule but it would be expected to be labile at
pH values above 10. | [Pesticide Type]
Insecticide |
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