JH III

Base Information

• Chemical Name: JH III
• CAS No.: 22963-93-5
• Deprecated CAS: 59597-77-2
• Molecular Formula: C16H26 O3
• Molecular Weight: 266.381
• Hs Code.: 2918990090
• UNII: B74U6BJ6J5
• DSSTox Substance ID: DTXSID1042659
• Metabolomics Workbench ID: 28199
• NCI Thesaurus Code: C64187
• Nikkaji Number: J37.976J,J2.915.674C
• Wikidata: Q27103163
• Mol file: 22963-93-5.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 JH III

Chemical Property:

• Refractive Index: nD24 1.4736
• 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:

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

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)/CC[C@@H]1C(O1)(C)C

Technology Process of JH III

There total 22 articles about JH III 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: 79.4%

methyl (2E,6E,10S)-11-hydroxy-10-mesyloxy-3,7,11-trimethyl-2,6-dodecadienoate (116536-45-9) → Juvenile hormone III (22963-93-5,5299-11-6)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 0.25h;

DOI:10.1016/S0040-4020(01)83448-7

Reference yield: 66.0%

(2E,5E)-9-((R)-3,3-Dimethyl-oxiranyl)-3-methyl-7-methylene-nona-2,5-dienoic acid methyl ester (121287-00-1) → Juvenile hormone III (22963-93-5,5299-11-6)

Guidance literature:

With hydrogen; tricarbonyl(naphthalene)chromium⁽⁰⁾; In tetrahydrofuran; at 45 ℃; for 5h; under 60800 Torr;

DOI:10.1016/S0040-4039(00)80312-3

Reference yield:

Methyl 3,3-dimethylacrylate (924-50-5) → Juvenile hormone III (22963-93-5,5299-11-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / N-bromosuccinimide / CCl₄

2: 1.) Bu₃SnCH=CHSnBu₃ 2.) cesium fluoride / 1.) bis(acetonitrile)dichloropalladium 2.) tetrakis(triphenylphosphine)palladium / 2.) THF reflux, 5 h

3: 66 percent / H2 / tricarbonyl<(1,2,3,4,4a,8a-η)naphtalene>chrominum / tetrahydrofuran / 5 h / 45 °C / 60800 Torr

With N-Bromosuccinimide; hydrogen; 1,2-bis(tributylstannyl)ethylene; cesium fluoride; dichloro bis(acetonitrile) palladium(II); tetrakis(triphenylphosphine) palladium⁽⁰⁾; tricarbonyl(naphthalene)chromium⁽⁰⁾; In tetrahydrofuran; tetrachloromethane;

DOI:10.1016/S0040-4039(00)80312-3

upstream raw materials:

(2E,5E)-9-((R)-3,3-Dimethyl-oxiranyl)-3-methyl-7-methylene-nona-2,5-dienoic acid methyl ester

methyl (2E,6E,10S)-(-)-10,11-dihydroxy-3,7,11-trimethyl-2,6-dodecadienoate

methyl (2E,6E,10S)-11-hydroxy-10-mesyloxy-3,7,11-trimethyl-2,6-dodecadienoate

methyl (E,E)-farnesoate

Downstream raw materials:

acetone

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

Refernces

• 1、 Crispino,Sharpless. "Enantioselective synthesis of juvenile hormone III in three steps from methyl farnesoate". . p. 777 - 779. Retrieved 1993.
• 2、 Mori, Kenji,Mori, Hideto. "SYNTHESIS OF BOTH THE ENANTIOMERS OF JUVENILE HORMONE III". . p. 4097 - 4106. Retrieved 2007/10/02.