| Identification | Back Directory | [Name]
S-(+)-METHOPRENE | [CAS]
65733-16-6 | [Synonyms]
(7S)-Form
S-METHOPRENE
D-Methoprene
7S-Methoprene
S-(+)-METHOPRENE
Flea killer plus
Epa pesticide chemical code 105402
S-Methoprene @100 μg/mL in Methanol
S-Methoprene 11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate
(S,2E,4E)-Isopropyl 11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate
Isopropyl (2E,4E,7S)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate
Isopropyl (2E,4E,7S)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate
(2E,4E,7S)-1-Methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate
(2E,4E,7S)-11-Methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid isopropyl ester
(2E,4E,7S-)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid isopropyl ester
Prop-2-yl (2E,4E,7S)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate, S-(+)-Methoprene
2,4-Dodecadienoic acid, 11-methoxy-3,7,11-trimethyl-, 1-methylethyl ester, (2E,4E,7S)- | [EINECS(EC#)]
202-303-5 | [Molecular Formula]
C19H34O3 | [MDL Number]
MFCD00867612 | [MOL File]
65733-16-6.mol | [Molecular Weight]
310.47 |
| Chemical Properties | Back Directory | [Boiling point ]
385.7±25.0 °C(Predicted) | [density ]
0.913±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 20 mg/ml,Ethanol: 10 mg/ml | [form ]
A neat oil | [color ]
Colorless to light yellow | [Henry's Law Constant]
1.5×100 mol/(m3Pa) at 25℃, Ebert et al. (2023) | [Stability:]
Light Sensitive | [InChI]
InChI=1S/C19H34O3/c1-15(2)22-18(20)14-17(4)11-8-10-16(3)12-9-13-19(5,6)21-7/h8,11,14-16H,9-10,12-13H2,1-7H3/b11-8+,17-14+/t16-/m1/s1 | [InChIKey]
NFGXHKASABOEEW-GYMWBFJFSA-N | [SMILES]
C(OC(C)C)(=O)/C=C(\C)/C=C/C[C@@H](C)CCCC(OC)(C)C | [EPA Substance Registry System]
S-Methoprene (65733-16-6) |
| Hazard Information | Back Directory | [Description]
(S)-(+)-Methoprene is a widely-used insect growth regulator. It is remarkable for its lack of significant effects against a wide variety of mammals, although concerns remain for its effects on arthropod development. Methoprene acts as an activator of the juvenile hormone receptor, known as Methoprene-tolerant or Met (Kd = 12.3 nM). Met is a transcription factor that, upon activation with juvenile hormone or methoprene, regulates gene expression that inhibits metamorphosis. | [Uses]
Insect Growth Regulator | [Uses]
Insecticide; insect growth regulator. | [Definition]
ChEBI: (S)-methoprene is a methoprene. It is an enantiomer of a (R)-methoprene. | [Production Methods]
The production of S-methoprene involves a multi-step organic synthesis starting from optically active precursors. One established method begins with (+)-dihydromyrcene, which undergoes selective hydroalumination followed by oxidation to yield S-(–)-citronellol. This intermediate is further oxidised to S-(–)-citronellal, which reacts with allylmagnesium chloride to form a key alcohol. Subsequent steps include Smidt-Moiseev oxygenation, dehydration, and Grignard reactions to build the conjugated diene ester backbone. The final transformation involves Brown solvomercuration-reduction in methanol, yielding S-methoprene with high stereochemical purity and biological activity. | [Mechanism of action]
A juvenile hormone mimic (terpene). Contact and stomach action, acts by mimicing the action of the juvenile hormone keeping the insect in an immature state | [Side effects]
S)-methoprene alone is well tolerated by dogs and cats, with a low toxicity and high safety margin. Side effects experienced by dogs and cats after treatment with products containing (S)-methoprene can generally be attributed to the other active or inert ingredients.
| [References]
[1] SIDDALL J B. Insect growth regulators and insect control: a critical appraisal.[J]. Environmental Health Perspectives, 1976, 14: 119-126. DOI: 10.1289/ehp.7614119
[2] WRIGHT J E. Environmental and toxicological aspects of insect growth regulators.[J]. Environmental Health Perspectives, 1976, 14: 127-132. DOI: 10.1289/ehp.7614127
[3] JEAN-PHILIPPE CHARLES. Ligand-binding properties of a juvenile hormone receptor, Methoprene-tolerant.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2011: 21128-21133. DOI: 10.1073/pnas.1116123109
[4] E. OSIR L R. Nuclear binding sites for juvenile hormone and its analogs in the epidermis of the tobacco hornworm.[J]. The Journal of Biological Chemistry, 1988, 23 1: 13812-13818. DOI: 10.1016/s0021-9258(18)68316-4
[5] ZHEN ZOU. Juvenile hormone and its receptor, methoprene-tolerant, control the dynamics of mosquito gene expression.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2013: E2173-81. DOI: 10.1073/pnas.1305293110 | [Pesticide Type]
Insecticide; Veterinary substance |
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