| Identification | Back Directory | [Name]
METHOPRENE ACID | [CAS]
53092-52-7 | [Synonyms]
Einecs 258-355-4
Methoprene acid >=98% (TLC)
11-methoxy-3,7,11-trimethyl-,(e,e)-(+/-)-4-dodecadienoicacid
(2E,4E)-(±)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoic 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)-
(+-)-(2E,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid | [EINECS(EC#)]
258-355-4 | [Molecular Formula]
C16H28O3 | [MDL Number]
MFCD01317817 | [MOL File]
53092-52-7.mol | [Molecular Weight]
268.39 |
| Chemical Properties | Back Directory | [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. | [InChI]
1S/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+ | [InChIKey]
MNYBEULOKRVZKY-TZOAMJEDSA-N | [SMILES]
COC(C)(C)CCCC(C)C\C=C\C(C)=C\C(O)=O | [EPA Substance Registry System]
2,4-Dodecadienoic acid, 11-methoxy-3,7,11-trimethyl-, (2E,4E)- (53092-52-7) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26-36 | [WGK Germany ]
3 | [TSCA ]
Yes | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [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) 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 |
|
| Company Name: |
Sigma-Aldrich
|
| Tel: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
| Company Name: |
Energy Chemical
|
| Tel: |
021-58432009 400-005-6266 |
| Website: |
http://www.energy-chemical.com |
| Company Name: |
Enzo Biochem Inc
|
| Tel: |
Enzo Biochem Inc. 13797054060 |
| Website: |
www.enzo.com |
| Company Name: |
Merck KGaA
|
| Tel: |
21-20338288 |
| Website: |
www.sigmaaldrich.cn |
| Company Name: |
SIGMA-RBI
|
| Tel: |
800 736 3690 (Orders) |
| Website: |
www.sigma-aldrich.com |
|