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Merck
CN

M6682

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
NACRES:
NA.77
PubChem Substance ID:
24897104
UNSPSC Code:
12352106
MDL number:
MFCD01317817

Key Documents

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Product Name

Methoprene acid, ≥98% (TLC)

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+

SMILES string

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

InChI key

MNYBEULOKRVZKY-TZOAMJEDSA-N

assay

≥98% (TLC)

storage temp.

−20°C

Quality Level

200

Related Categories

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.

General description

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

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SLCR3633
SLCH8553
SLCF9799
SLCD6704
SLCD2006

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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.
Juvenile Hormones: Advances in Research and Application (2012)
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)
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
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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