(Z,Z)-Gossyplure

Base Information

• Chemical Name: (Z,Z)-Gossyplure
• CAS No.: 50933-33-0
• Molecular Formula: C18H32 O2
• Molecular Weight: 280.451
• Hs Code.: 2915390090
• European Community (EC) Number: 256-857-8,257-737-8
• UNII: W52P5A61DR
• DSSTox Substance ID: DTXSID9035751
• Nikkaji Number: J184.552G
• Wikidata: Q27292319
• Metabolomics Workbench ID: 4020
• Mol file: 50933-33-0.mol

Synonyms:gossyplure

Chemical Property of (Z,Z)-Gossyplure

Chemical Property:

• Appearance/Colour: light yellow liquid
• Melting Point: <25℃
• Boiling Point: 365.7 °C at 760 mmHg
• Flash Point: 102.1 °C
• PSA: 52.60000
• Density: 0.886 g/cm³
• LogP: 11.16560
• XLogP3: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 14
• Exact Mass: 280.240230259
• Heavy Atom Count: 20
• Complexity: 267

Purity/Quality:

99% ^*data from raw suppliers

7,11-Hexadecadien-1-ylAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Extremely flammable.
• Hazard Codes: Extremely flammable.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC=CCCC=CCCCCCCOC(=O)C
• Isomeric SMILES: CCCC/C=C\CC/C=C\CCCCCCOC(=O)C
• Uses: 7,11-Hexadecadien-1-yl Acetate is a pheromone which can be used to disrupt the mating patterns of cotton bollworms and hence control their populations. It is also a fatty acid component of the Akebia trifoliata seed. Sex attractant for pink bollworm

Technology Process of (Z,Z)-Gossyplure

There total 18 articles about (Z,Z)-Gossyplure 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: 75.0%

acetic anhydride (108-24-7) + (7E/Z,11Z/E)-7,11-hexadecadien-1-ol (59741-58-1) → (7E/Z,11Z/E)-7,11-hexadecadien-1-yl acetate (50933-33-0)

Guidance literature:

With pyridine;

Reference yield:

(1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) → (7E/Z,11Z/E)-7,11-hexadecadien-1-yl acetate (50933-33-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) O₃/O₂, 2.) NaOAc, AcOH, Ac₂O / 1.) AcOH, cyclohexane, 5 deg C, 2.) from 30 to 40 deg C, 1.5 h

2: p-toluenesulfonic acid / 24 h / Ambient temperature

3: 90 percent / diisobutylaluminium hydride / diethyl ether; toluene / 1.5 h / -10 °C

4: 100 percent / pyridine / 20 h / 0 °C

5: 1.) CuI / 1.) Et₂O, -5 deg C, 40 min, 2.) Et₂O, from -5 to 0 deg C, 15 h

6: 95 percent / 10percent aq. HCl / acetone / 6 h

7: 1.) Mg / 1.) THF, 2.) THF, RT, 3 h

8: pyridine / 20 h / 0 °C

9: NaI, Zn / tetrahydrofuran / 3 h / Heating

10: 95 percent / 10percent aq. HCl / acetone / 6 h / 40 °C

11: 95 percent / diisobutylaluminium hydride / diethyl ether; toluene / 1.5 h / -10 °C

12: 75 percent / pyridine

With pyridine; hydrogenchloride; copper(l) iodide; oxygen; sodium acetate; acetic anhydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; magnesium; acetic acid; sodium iodide; zinc; In tetrahydrofuran; diethyl ether; acetone; toluene;

Reference yield:

(4E/Z,8Z/E)-4,8-tridecadienal (131392-54-6,131392-66-0,131392-67-1,131392-68-2) → (7E/Z,11Z/E)-7,11-hexadecadien-1-yl acetate (50933-33-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) Mg / 1.) THF, 2.) THF, RT, 3 h

2: pyridine / 20 h / 0 °C

3: NaI, Zn / tetrahydrofuran / 3 h / Heating

4: 95 percent / 10percent aq. HCl / acetone / 6 h / 40 °C

5: 95 percent / diisobutylaluminium hydride / diethyl ether; toluene / 1.5 h / -10 °C

6: 75 percent / pyridine

With pyridine; hydrogenchloride; diisobutylaluminium hydride; magnesium; sodium iodide; zinc; In tetrahydrofuran; diethyl ether; acetone; toluene;

upstream raw materials:

acetic anhydride

(7E/Z,11Z/E)-7,11-hexadecadien-1-ol

(1E,5E,9Z)-cyclododeca-1,5,9-triene

(4E/Z,8Z/E)-4,8-tridecadienal

Refernces

• 1、 Odinokov, V. N.,Mukhametzyanova, R. S.,Galeeva, R. I.,Ishmuratov, G. Yu.,Tolstikov, G. A.. "OZONOLYSIS OF ALKENES AND THE REACTIONS OF POLYFUNCTIONAL COMPOUNDS XL. SYNTHESIS OF (Z,Z)-, (E,E)-, AND (E/Z,Z/E)-7,11-HEXADECADIEN-1-YL ACETATES - COMPONENTS OF THE SEX PHEROMONE OF PECTINOPHORA GOSSYPIELLA (SAUNDERS)". . p. 1399 - 1407. Retrieved 2007/10/02.