65733-16-6

Basic information

• Product Name: S-(+)-METHOPRENE
• Synonyms: S-(+)-METHOPRENE;S-METHOPRENE;2,4-Dodecadienoic acid, 11-methoxy-3,7,11-trimethyl-, 1-methylethyl ester, (2E,4E,7S)-;(2E,4E,7S-)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid isopropyl ester;(2E,4E,7S)-11-Methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid isopropyl ester;7S-Methoprene;(2E,4E,7S)-1-Methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate;D-Methoprene
• CAS NO: 65733-16-6
• Molecular Formula: C₁₉H₃₄O₃
• Molecular Weight: 310.47
• Mol File: 65733-16-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 385.7 °C at 760 mmHg
• Flash Point: 162.4 °C
• Appearance: /
• Density: 0.913 g/cm³
• Vapor Pressure: 3.74E-06mmHg at 25°C
• Refractive Index: 1.462
• CAS DataBase Reference: S-(+)-METHOPRENE(CAS DataBase Reference)
• NIST Chemistry Reference: S-(+)-METHOPRENE(65733-16-6)
• EPA Substance Registry System: S-(+)-METHOPRENE(65733-16-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 65733-16-6(Hazardous Substances Data)

Usage

Description

(S)-(+)-Methoprene is a widely-used insect growth regulator. It is remarkable for its lack of significant effects against a wide variety of mammals, although concerns remain for its effects on arthropod development. Methoprene acts as an activator of the juvenile hormone receptor, known as Methoprene-tolerant or Met (Kd = 12.3 nM). Met is a transcription factor that, upon activation with juvenile hormone or methoprene, regulates gene expression that inhibits metamorphosis.

Uses

Different sources of media describe the Uses of 65733-16-6 differently. You can refer to the following data:
1. Insect Growth Regulator
2. Insecticide; insect growth regulator.

InChI:InChI=1/C19H34O3/c1-15(2)22-18(20)14-17(4)11-8-10-16(3)12-9-13-19(5,6)21-7/h8,11,14-16H,9-10,12-13H2,1-7H3/b11-8+,17-14-/t16-/m1/s1

Upstream product

• 134678-53-8 S-(-)-7-methoxy-3,7-dimethyloctanal 
• 87359-86-2 diisopropyl (E)-3-isopropylcarbonyl-2-methyl-2-propenylphosphonate 
• 24425-00-1 diisopropyl pyrocarbonate 
• 207597-75-9 (2E,4E,7S)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid 
• 2436-90-0 (S)-(+)-dihydromyrcene 
• 38376-28-2 7-methoxy-3,7-dimethyloctan-1-ol 
• 50798-35-1 diisopropyl ester of 2-methyl-3-isopropoxycarbonyl-2-propenylphosphonic acid 
• 33027-94-0 4-hydroxy-6,10-dimethylundec-9-en-2-one 
• 19870-49-6 (E)-6,10-dimethylundeca-3,9-dien-2-one 
• 90660-54-1 6,10-dimethylundeca-1,9-dien-4-ol 
• 106-23-0 3,7-dimethyl-oct-6-enal 
• 67-56-1 methanol 
• 41797-08-4 isopropyl 3,7,11-trimethyl-2ξ,4E,10-dodecatrienoate 
• 134600-30-9 S-(+)-7-methoxy-3,7-dimethyl-1-octene 

Downstream Products

• 36557-30-9 (S)-hydroprene 
• 207597-79-3 all-trans-S-methoprene epoxide 
• 207597-75-9 (2E,4E,7S)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid 

Relevant articles and documents

A juvenile hormone analogs of the preparation method

The invention relates to the field of insecticides, and particularly relates to a preparation method of a juvenile hormone analogue (which comprises S-methoprene and S-hydroprene). The preparation method of the juvenile hormone analogues comprises the following steps of: A. adding (2E, 4E)-11-R-3,7,11-trimethyl-2,4-dodecadienoic acid (R is hydrogen or methoxyl) serving as raw material, an organic alkali catalyst and an organic solvent to a reaction vessel, and starting stirring; B. dropwise adding an organic solvent (the same as the organic solvent in the step A) solution of pyrocarbonate; C. after the addition is completed, reacting at 0-30 DEG C for 0-3 hours; D. adding water to stop reaction, and splitting phases of reaction liquid to obtain an organic phase; E. carrying out reduced pressure concentration and distillation to obtain a product, wherein the steps can also be carried out under the condition that the addition sequences of the pyrocarbonate and an organic strongly-alkaline catalyst are exchanged. The preparation method disclosed by the invention has the advantages of mild reaction condition, high product purity, high yield, environment-friendly and safe route and good industrial prospect.

Synthesis of S-(+)-methoprene

An optically active juvenile hormone analogue, S-(+)-methoprene (1), is synthesized in six steps from technical grade S-(+)-3,7-dimethyl-1,6-octadiene (''(+)-dihydromyrcene'', e.e. ca. 50percent) by a novel procedure which begins with selective hydroalumination-oxidation to give S-(-)-citronellol.This alcohol is oxidized to give S-(-)-citronellal which on reaction with allylmagnesium chloride affords 6S,10-dimethyl-1,9-undecadien-4R/S-ol (5).Smidt-Moiseev oxygenation of 5 followed by dehydration leads to 6S,10-dimethyl-3E,9-undecadien-2-one.The latter on treatment with isopropoxyethynylmagnesium bromide is transformed into isopropyl 3,7S,11-trimethyl-2E/Z,4E,10-dodecatrienoate which upon Brown solvomercuration-reduction in MeOH gives 1 in 14percent overall yield.