S-Methoprene

Base Information

• Chemical Name: S-Methoprene
• CAS No.: 65733-16-6
• Molecular Formula: C19H34O3
• Molecular Weight: 310.477
• Hs Code.: 2918999090
• European Community (EC) Number: 613-834-0
• NSC Number: 758655
• UNII: 4YIQ0A94UR
• DSSTox Substance ID: DTXSID1035783
• Nikkaji Number: J344.494E
• Wikidata: Q27119791
• Metabolomics Workbench ID: 56208
• ChEMBL ID: CHEMBL1875086
• Mol file: 65733-16-6.mol

Synonyms:Altosid;Altosid PS 10;Altosid PS-10;Altosid PS10;Methoprene;ZR 515;ZR-515;ZR515

Chemical Property of S-Methoprene

Chemical Property:

• Vapor Pressure: 3.74E-06mmHg at 25°C
• Refractive Index: 1.462
• Boiling Point: 385.7 °C at 760 mmHg
• Flash Point: 162.4 °C
• PSA: 35.53000
• Density: 0.913 g/cm³
• LogP: 5.06200
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 11
• Exact Mass: 310.25079494
• Heavy Atom Count: 22
• Complexity: 378

Purity/Quality:

99.9% ^*data from raw suppliers

(S)-(+)-Methoprene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)OC(=O)C=C(C)C=CCC(C)CCCC(C)(C)OC
• Isomeric SMILES: C[C@@H](CCCC(C)(C)OC)C/C=C/C(=C/C(=O)OC(C)C)/C
• 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: Insect Growth Regulator Insecticide; insect growth regulator.

Technology Process of S-Methoprene

There total 17 articles about S-Methoprene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.3%

diisopropyl pyrocarbonate (24425-00-1) + (2E,4E,7S)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid (207597-75-9,207597-76-0) → (S)-methoprene (65733-16-6)

Guidance literature:

With dmap; In toluene; at 15 - 25 ℃; for 3h; Reagent/catalyst; Solvent; Temperature; Green chemistry;

Reference yield:

S-(-)-7-methoxy-3,7-dimethyloctanal (134678-53-8) + diisopropyl (E)-3-isopropylcarbonyl-2-methyl-2-propenylphosphonate (87359-86-2) → (S)-methoprene (65733-16-6) + 2-trans-4-cis-S-methoprene

Guidance literature:

With potassium hydroxide; tetraoctyl ammonium bromide; In water; benzene; at 20 - 22 ℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Reference yield:

S-(+)-7-methoxy-3,7-dimethyloctan-1-ol (114807-42-0) → (S)-methoprene (65733-16-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / 4-Bz-TEMPO, NaBr, NaHCO₃ / CH₂Cl₂ / 5 - 10 °C / electrolysis

2: KOH, Oct₄NBr / benzene; H₂O / 3 h / 20 - 22 °C

With potassium hydroxide; 4-hydroxy-TEMPO benzoate; sodium hydrogencarbonate; tetraoctyl ammonium bromide; sodium bromide; In dichloromethane; water; benzene;

upstream raw materials:

methanol

isopropyl 3,7,11-trimethyl-2ξ,4E,10-dodecatrienoate

3,7-dimethyl-oct-6-enal

6,10-dimethylundeca-1,9-dien-4-ol

Downstream raw materials:

(2E,4E,7S)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid

all-trans-S-methoprene epoxide

(S)-hydroprene

Refernces

• 1、 Gamalevich,Zhdankina,Kryshtal',Nikishin,Ogibin,Serebryakov. "Combined Biochemical and Electrochemical Approach to Chiral C10-Components for Juvenoid Synthesis, and Preparation of (2E,4E,7S)Stereoisomers of Metoprene and Hydroprene". . p. 467 - 474. Retrieved 2007/10/03.
• 2、 Serebryakov, E. P.,Zhdankina, G. M.,Kryshtal', G. V.,Mavrov, M. V.,Khao, Nguen Kong. "TERPENES IN ORGANIC SYNTHESIS. 13. SYNTHESIS OF S-(+)-METHOPRENE FROM (+)-&β-CITRONELLENE". . p. 739 - 743. Retrieved 2007/10/02.