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M6682

Sigma-Aldrich

Methoprene acid

≥98% (TLC)

Synonym(s):

11-Methoxy-3,7,11-trimethyl-2E,4E-dodecadienoic acid

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About This Item

Empirical Formula (Hill Notation):
C16H28O3
CAS Number:
53092-52-7
Molecular Weight:
268.39
MDL number:
MFCD01317817
UNSPSC Code:
12352106
PubChem Substance ID:
24897104
NACRES:
NA.77

Quality Level

200

assay

≥98% (TLC)

storage temp.

−20°C

SMILES string

COC(C)(C)CCCC(C)C\C=C\C(C)=C\C(O)=O

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+

InChI key

MNYBEULOKRVZKY-TZOAMJEDSA-N

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Juvenile Hormones: Advances in Research and Application (2012)
M A Harmon et al.
Proceedings of the National Academy of Sciences of the United States of America, 92(13), 6157-6160 (1995-06-20)
We report that methoprene and its derivatives can stimulate gene transcription in vertebrates by acting through the retinoic acid-responsive transcription factors, the retinoid X receptors (RXRs). Methoprene is an insect growth regulator in domestic and agricultural use as a pesticide.
Rintaro Suzuki et al.
Scientific reports, 1, 133-133 (2012-02-23)
Juvenile hormone (JH) plays crucial roles in many aspects of the insect life. All the JH actions are initiated by transport of JH in the hemolymph as a complex with JH-binding protein (JHBP) to target tissues. Here, we report structural
Occurrence and fate of methoprene compounds in urban areas of Southern Ontario, Canada
Struger J, et al.
Bulletin of Environmental Contamination and Toxicology, 79(2), 168-171 (2007)
Daniel Jahn et al.
Biochimica et biophysica acta, 1859(2), 381-392 (2016-01-03)
Fibroblast growth factor 19 (FGF19) is a gut-derived hormone that controls bile acid (BA), carbohydrate and lipid metabolism. Whereas strong evidence supports a key role of BAs and farnesoid X receptor (FXR) for the control of FGF19 expression, information on

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