METHOPRENE ACID Chemical Properties

Boiling point:

394.1±25.0 °C(Predicted)

Density 

0.954±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Soluble in DMSO or Ethanol

form 

Pale yellow oil.

pka

4.96±0.33(Predicted)

color 

Colorless

Stability:

Stable for 2 years as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.

EPA Substance Registry System

2,4-Dodecadienoic acid, 11-methoxy-3,7,11-trimethyl-, (2E,4E)- (53092-52-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

Yes

METHOPRENE ACID Usage And Synthesis

Description

Methoprene Acid (53093-52-7) is an analog of insect juvenile hormone which acts as an insect growth regulator. Binds directly and selectively to the retinoid X receptor (RXR) acting as a transcriptional activator in both insect and mammalian cells with no activity at RAR.1?Negatively regulates thrombosis and hemostasis.2?Induces neurosteroid biosynthesis in human glial GI-1 cells.3?Increases the expression of the brown-fat-uncoupling-protein-1 gene (ucp-1).4

Uses

Methoprene Acid is an analog of insect juvenile hormone which acts as an insect growth regulator.

Definition

ChEBI: 11-methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid is a sesquiterpenoid.

General Description

Retinoic acid receptor (RXR) agonist used in gene regulation research. Analog of juvenile hormone, an insect growth hormone.

Biochem/physiol Actions

Demethylation, oxidative cleavage, hydrolysis, photodegradation and degradation of methoprene by microorganism results in methoprene acid and other metabolites. Methoprene acid is an insect growth regulator, and is known to control ecdysteroid signaling during development and metamorphism. It is thus used to control larval growth in insects such as mosquitoes, cigarette beetles, fleas and fire ants.

References

[1] M A HARMON. Activation of mammalian retinoid X receptors by the insect growth regulator methoprene.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1995, 92 13: 6157-6160. DOI:10.1073/pnas.92.13.6157
[2] AMANDA J UNSWORTH. RXR Ligands Negatively Regulate Thrombosis and Hemostasis.[J]. Arteriosclerosis, Thrombosis, and Vascular Biology, 2017, 37 5: 812-822. DOI:10.1161/atvbaha.117.309207
[3] AKIRA KUSHIDA  Hiroomi T. Retinoic acids induce neurosteroid biosynthesis in human glial GI-1 Cells via the induction of steroidogenic genes.[J]. Journal of biochemistry, 2009, 146 6: 917-923. DOI:10.1093/jb/mvp142
[4] R. ALVAREZ. Both retinoic-acid-receptor- and retinoid-X-receptor-dependent signalling pathways mediate the induction of the brown-adipose-tissue-uncoupling-protein-1 gene by retinoids.[J]. The Ukrainian Biochemical Journal, 2000, 1 1: 91-97. DOI:10.1042/bj3450091

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