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
• Uses: trans-trans-10,11-Epoxy Farnesenic Acid Methyl Ester is a metabolite (2E,6E)-Farnesenic Acid. Juvenile hormone III has been used to:study the effect of juvenile hormone on mictic (sexual) female production of the rotifer Brachionus plicatilis Mullerstudy the effect of juvenile hormone on head GB19811 (putative Takeout/juvenile hormone binding protein) mRNA levels in adult honeybeesstudy the effect of juvenile hormone on gonadotropic and physiological functions in bumblebee Bombus terrestris

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:

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

C₁₆H₂₆O₃

Refernces

• 1、 Ichikawa, Akio,Takenaka, Makiko,Ono, Hiroshi. "First preparation of single-enantiomer juvenile hormone III acid and (R)-juvenile hormone III-d3". experimental part. p. 1800 - 1806. Retrieved 2011/02/23.
• 2、 Lluch, Anna-Maria,Sanchez-Baeza, Francisco,Messeguer, Angel,Fusco, Caterina,Curci, Ruggero. "Regio- and Chemoselective Epoxidation of Fluorinated Monoterpenes and Sesquiterpenes by Dioxiranes". . p. 6299 - 6308. Retrieved 2007/10/02.