JH III Bisepoxide

Base Information

• Chemical Name: JH III Bisepoxide
• CAS No.: 120293-93-8
• Molecular Formula: C16H26 O4
• Molecular Weight: 282.38
• DSSTox Substance ID: DTXSID101108658
• Nikkaji Number: J534.624J,J635.378I
• Mol file: 120293-93-8.mol

Synonyms:6,7,10,11-bisepoxy-3,7,11-trimethyl-2-dodecenoic acid methyl ester;JH III bisepoxide;JHB3;juvenile hormone III bisepoxide;methyl 6,7-10,11-bis(epoxy)-3,7,11-trimethyl-2-dodecenoate

Chemical Property of JH III Bisepoxide

Chemical Property:

• Vapor Pressure: 4.02E-05mmHg at 25°C
• Boiling Point: 351.8°C at 760 mmHg
• Flash Point: 150.4°C
• PSA: 51.36000
• Density: 1.023g/cm³
• LogP: 3.00100
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 282.18310931
• Heavy Atom Count: 20
• Complexity: 413

Purity/Quality:

99%, ^*data from raw suppliers

JuvenileHormoneB3(MixtureofDiastereomers),TechnicalGrade ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC(=O)OC)CCC1C(O1)(C)CCC2C(O2)(C)C
• Isomeric SMILES: C/C(=C\C(=O)OC)/CCC1C(O1)(C)CCC2C(O2)(C)C
• Uses: Juvenile Hormone B 3 is a sesquiterpenoid produced by the larval ring gland and adult corpus allatum (CA) of Drosophila melanogaster. Juvenile hormones regulate development, reproduction, diapause, and polyphenisms.

Technology Process of JH III Bisepoxide

There total 28 articles about JH III Bisepoxide 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: 49.0%

(2E,4E)-5-{(2S,3S)-3-[2-((R)-3,3-Dimethyl-oxiranyl)-ethyl]-3-methyl-oxiranyl}-3-methyl-penta-2,4-dienoic acid methyl ester → methyl (2E,6E)-6,7;10,11-bisepoxy-3,7,11-trimethyl-2-dodecenoate (120293-93-8)

Guidance literature:

With hydrogen; RhCl(PPh₃)3;

DOI:10.1016/S0040-4039(00)74741-1

Reference yield:

trans geranyl acetone (3796-70-1) → 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)

Guidance literature:

Multi-step reaction with 3 steps

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

2: m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.5 h

3: P₄₅₀ 6A₁; NADPH-cytochrome P₄₅₀ reductase / 0.33 h / Enzymatic reaction

With P₄₅₀ 6A₁; sodium hydride; 3-chloro-benzenecarboperoxoic acid; NADPH-cytochrome P₄₅₀ reductase; In dichloromethane; N,N-dimethyl-formamide; 1: Wittig reaction;

DOI:10.1021/tx9601162

Reference yield:

(Z)-nerylacetone (3879-26-3) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: 26 percent / NaH / dimethylformamide / 18 h / 20 °C

2: P₄₅₀ 6A₁; NADPH-cytochrome P₄₅₀ / 0.33 h / Enzymatic reaction

With NADPH-cytochrome P₄₅₀; P₄₅₀ 6A₁; sodium hydride; NADPH; In N,N-dimethyl-formamide; 1: Wittig reaction;

DOI:10.1021/tx9601162

upstream raw materials:

methyl (2Z,6E)-10,11-epoxyfarnesoate

methyl (2Z,6Z)-farnesenate

methyl (6E)-farnesoate

methyl (2Z)-6,7-epoxyfarnesoate

Refernces

• 1、 Andersen, John F.,Walding, Jennifer K.,Evans, Philip H.,Bowers, William S.,Feyereisen, Rene. "Substrate specificity for the epoxidation of terpenoids and active site topology of house fly cytochrome P450 6A1". . p. 156 - 164. Retrieved 2007/10/03.
• 2、 Rickards, Rodney W.,Thomas, Richard D.. "An efficient asymmetric synthesis of the higher dipteran juvenile hormone III bisepoxide". . p. 8369 - 8372. Retrieved 2007/10/02.