53092-52-7

Basic information

• Product Name: METHOPRENE ACID
• Synonyms: 11-methoxy-3,7,11-trimethyl-,(e,e)-(+/-)-4-dodecadienoicacid;(2E,4E)-(±)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid;(+-)-(2E,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid;(2E,4E)-(1)-11-Methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid;2,4-Dodecadienoic acid, 11-methoxy-3,7,11-trimethyl-, (2E,4E)-;Einecs 258-355-4
• CAS NO: 53092-52-7
• Molecular Formula: C₁₆H₂₈O₃
• Molecular Weight: 268.39172
• EINECS: 258-355-4
• Mol File: 53092-52-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 394.1°Cat760mmHg
• Flash Point: 134.2°C
• Appearance: /
• Density: 0.954g/cm³
• Vapor Pressure: 2.62E-07mmHg at 25°C
• Refractive Index: 1.476
• Storage Temp.: −20°C
• Solubility: Soluble in DMSO or Ethanol
• PKA: 4.96±0.33(Predicted)
• Stability: Stable for 2 years as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• CAS DataBase Reference: METHOPRENE ACID(CAS DataBase Reference)
• NIST Chemistry Reference: METHOPRENE ACID(53092-52-7)
• EPA Substance Registry System: METHOPRENE ACID(53092-52-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 53092-52-7(Hazardous Substances Data)

Usage

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.

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) Harmon?et al.?(1995),?Activation of mammalian retinoid X receptors by the insect growth regulator methoprene; Proc. Natl. Acad. Sci. USA,?92?6157 2) Unsworth?et al.?(2017),?RXR Ligands Negatively Regulate Thrombosis and Hemostasis; Arterioscler. Thromb. Vasc. Biol.,?37?812 3) Kushida and Tamura (2009),?Retinoic acids induce neurosteroid biosynthesis in human glial GL-1 cells via the induction of steroidogenic genes; J. Biochem.,?146?917 4) Alvarez?et al. (2000),?Both retinoic-acid-receptor and retinoid-X-receptor-dependent signaling pathways mediate the induction of the brown-adipose-tissue-uncoupling-protein-1 gene by retinoids; Biochem. J.,?345 Pt 1?91

InChI:InChI=1/C16H28O3/c1-13(10-7-11-16(3,4)19-5)8-6-9-14(2)12-15(17)18/h6,9,12-13H,7-8,10-11H2,1-5H3,(H,17,18)/b9-6+,14-12+

Upstream product

• 53023-65-7 (2Z,4E)-11-methoxy-3,7,11-trimethyl-dodeca-2,4-dienoic acid 
• 52313-82-3 6-(6-Methoxy-2,6-dimethyl-heptyl)-4-methyl-3,6-dihydro-pyran-2-one 

Downstream Products

• 40596-69-8 methoprene 

Relevant articles and documents

Stereoselective synthesis of alkyl (2E,4E) and (2Z,4E) 3,7,11 trimethyl 2,4 dodecadienoates. Insect growth regulators with juvenile hormone activity

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