S-(+)-METHOPRENE Chemical Properties

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

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)

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2918999090

S-(+)-METHOPRENE Usage And Synthesis

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 (K_d = 12.3 nM). Met is a transcription factor that, upon activation with juvenile hormone or methoprene, regulates gene expression that inhibits metamorphosis.

Uses

Insecticide; insect growth regulator.

Definition

ChEBI: (S)-methoprene is a methoprene. It is an enantiomer of a (R)-methoprene.

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

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