Juvenate

Base Information

• Chemical Name: Juvenate
• CAS No.: 24198-95-6
• Deprecated CAS: 76898-57-2,34769-49-8,5299-11-6,20143-98-0
• Molecular Formula: C16H26 O3
• Molecular Weight: 266.381
• Hs Code.: 2918990090
• European Community (EC) Number: 246-072-9
• NSC Number: 688246
• DSSTox Substance ID: DTXSID601033769
• Nikkaji Number: J142.412B,J3.044.914B
• Metabolomics Workbench ID: 125858
• ChEMBL ID: CHEMBL1967398
• Mol file: 24198-95-6.mol

Synonyms:10,11-epoxyfarnesenic acid methyl ester;juvenile hormone III;juvenile hormone III, (E,E)-(+-)-isomer;juvenile hormone III, (E,E)-isomer;juvenile hormone III, (R-(E,E))-isomer;juvenile hormone III, (S-(E,E))-isomer;juvenile hormone III, (Z,E)-isomer;methyl 10,11-epoxy-3,7,11-trimethyl-2,6-dodecanoate

Chemical Property of Juvenate

Chemical Property:

• Vapor Pressure: 4.98E-05mmHg at 25°C
• Boiling Point: 348.6°Cat760mmHg
• Flash Point: 144.9°C
• PSA: 38.83000
• Density: 0.966g/cm³
• LogP: 3.78980
• Storage Temp.: 2-8°C
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 266.18819469
• Heavy Atom Count: 19
• Complexity: 378

Purity/Quality:

98%,99%, ^*data from raw suppliers

trans-trans-10,11-EpoxyFarnesenicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=CCCC(=CC(=O)OC)C)CCC1C(O1)(C)C
• Isomeric SMILES: C/C(=C\CC/C(=C/C(=O)OC)/C)/CCC1C(O1)(C)C
• General Description: Juvenile Hormone III (JH III) is a sesquiterpenoid compound that plays a critical role in insect development, regulating metamorphosis, reproduction, and other physiological processes. It is characterized by its 2E,6E,10,11-epoxy-3,7,11-trimethyl-dodecadienoate structure and exists in both natural and synthetic racemic forms. The hormone is synthesized via stereospecific methods involving vinylcuprates and subsequent epoxidation, as demonstrated in studies focusing on efficient synthetic pathways for juvenile hormones and their analogues. JH III is widely studied for its biological significance in insects and potential applications in pest control.

Technology Process of Juvenate

There total 11 articles about Juvenate 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: 66.0%

methyl (E,E)-farnesoate (3675-00-1) → C(16)-juvenile hormone (24198-95-6,5299-11-6)

Guidance literature:

With N-Bromosuccinimide; In tetrahydrofuran; water; 1) 0 deg C, 1.5h, 2) 20 deg C, 1 h;

Reference yield:

methyl (E,E)-farnesoate (3675-00-1) → C(16)-juvenile hormone (24198-95-6,5299-11-6) + Methyl (2E)-6,7,10,11-diepoxy-3,7,11-trimethyldodec-2-enoate (25506-84-7,68000-79-3,120293-93-8,137822-38-9,137822-42-5,146276-67-7,146276-68-8) + methyl (2E)-6,7-epoxyfarnesoate (133707-14-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -20 ℃;

DOI:10.1016/S0040-4020(01)86022-1

Reference yield:

trans geranyl acetone (3796-70-1) → C(16)-juvenile hormone (24198-95-6,5299-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 22.5 percent / NaH / dimethylformamide / 18 h / 20 °C

2: m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.5 h

With sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide; 1: Wittig reaction;

DOI:10.1021/tx9601162

upstream raw materials:

methyl (E,E)-farnesoate

methyl (6E)-farnesoate

(E)-1,1-dimethoxy-8-oxo-4-methyl-4-nonene

methyl 3,7-dimethyl-10-oxo-2ξ,6E-decadienoate

Downstream raw materials:

C₁₆H₂₆O₃

Methyl (2E)-6,7,10,11-diepoxy-3,7,11-trimethyldodec-2-enoate

(2E,6E)-10,11-epoxy-3,7,11-trimethyldodeca-2,6-dienoic acid

Refernces

A convenient, stereospecific synthesis of racemic juvenile hormones and some of their analogues via vinylcuprates

10.1002/recl.19811000702

This research presents a stereospecific synthesis method for racemic juvenile hormones and some of their analogues, focusing on the creation of nine 2E,6E,10(Z)-trienyl esters and their conversion into corresponding epoxides, including natural hormones JH I-III. The study utilizes specifically substituted vinylcuprates, such as [R'R2C=CH-Cu-Y]', which react with 4-iodo-1-butyne to form the desired trienyl systems. The synthesis involves a series of reactions including the preparation of enynes, dienynes, and the final esters, using various cuprate species like R,Cu,MgX for the stereospecific conversion of 1-alkynes into vinylcuprates. The process also includes selective epoxidation using N-bromosuccinimide and potassium carbonate.

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