Methoprene

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Names

[ CAS No. ]:
40596-69-8

[ Name ]:
Methoprene

[Synonym ]:
Isopropyl (2E,4E)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate
Methoprene
EINECS 254-993-2
MFCD00072475
Isopropyl (2E,4E)-11-Methoxy-3,7,11-trimethyldodeca-trans-2,trans-4-dienoate
UNII:8B830OJ2UX
isopropyl (E,E)-(RS)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate
1-methylethyl (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate
2,4-Dodecadienoic acid, 11-methoxy-3,7,11-trimethyl-, 1-methylethyl ester, (2E,4E)-
1-methylene-indan-4-ol
1-Methylethyl (2E,4E)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate
isopropyl 11-methoxy-3,7,11-trimethyldodeca-2E,4E-1-dienoate
rac-propan-2-yl (2E,4E,7R)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate
juvemon
Isopropyl (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
385.7±25.0 °C at 760 mmHg

[ Melting Point ]:
164ºC

[ Molecular Formula ]:
C19H34O3

[ Molecular Weight ]:
310.471

[ Flash Point ]:
162.4±17.8 °C

[ Exact Mass ]:
310.250793

[ PSA ]:
35.53000

[ LogP ]:
5.63

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.462

[ Storage condition ]:
0-6°C

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
JR1685000
CHEMICAL NAME :
2,4-Dodecadienoic acid, 11-methoxy-3,7,11-trimethyl-, 1-methylethyl ester, (E,E)-
CAS REGISTRY NUMBER :
40596-69-8
LAST UPDATED :
199606
DATA ITEMS CITED :
11
MOLECULAR FORMULA :
C19-H34-O3
MOLECULAR WEIGHT :
310.53
WISWESSER LINE NOTATION :
1Y1&OV1UY1&1U2Y1&3X1&1&O1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
25 gm/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - body temperature decrease
TYPE OF TEST :
LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>210 gm/m3
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
3038 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
3 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
>210 gm/m3
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
84 mg/kg/3W-I
TOXIC EFFECTS :
Endocrine - changes in adrenal weight Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
Specific locus test

MUTATION DATA

TYPE OF TEST :
Mutation test systems - not otherwise specified
TEST SYSTEM :
Insect - not otherwise specified Ovary
DOSE/DURATION :
100 umol/L
REFERENCE :
ABCHA6 Agricultural and Biological Chemistry. (Maruzen Co. Ltd., POB 5050, Tokyo International, Tokyo 100-31, Japan) V.25- 1961- Volume(issue)/page/year: 43,1285,1979 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989

Safety Information

[ Symbol ]:

GHS07, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335-H411

[ Precautionary Statements ]:
P261-P273-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
Xi: Irritant;N: Dangerous for the environment;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36-60-61

[ RIDADR ]:
UN3082 9/PG 3

[ RTECS ]:
JR1685000

[ HS Code ]:
2918990090

Synthetic Route

Precursor & DownStream

Precursor

  • UNII:261VCL42SZ
  • isopropyl 2-hydroxy-3-methylbutanoate
  • isopropyl 11-methoxy-3,7,11-trimethyl-5-oxo-2-(tosyloxy)dodecanoate
  • 3-Methylthiophene
  • 6-bromo-2-methylhept-2-ene

DownStream

Customs

[ HS Code ]: 2918990090

[ Summary ]:
2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Methoprene-tolerant (Met) knockdown in the adult female cockroach, Diploptera punctata completely inhibits ovarian development.

PLoS ONE 9(9) , e106737, (2014)

Independent of the design of the life cycle of any insect, their growth and reproduction are highly choreographed through the action of two versatile hormones: ecdysteroids and juvenile hormones (JH)....

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PLoS Genet. 11(3) , e1005038, (2015)

Corpus allatum (CA) ablation results in juvenile hormone (JH) deficiency and pupal lethality in Drosophila. The fly CA produces and releases three sesquiterpenoid hormones: JH III bisepoxide (JHB3), J...

Ligand-binding properties of a juvenile hormone receptor, Methoprene-tolerant.

Proc. Natl. Acad. Sci. U. S. A. 108(52) , 21128-33, (2011)

Juvenile hormone (JH) is a sesquiterpenoid of vital importance for insect development, yet the molecular basis of JH signaling remains obscure, mainly because a bona fide JH receptor has not been iden...


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