11-cis Vaccenyl Acetate

Base Information

• Chemical Name: 11-cis Vaccenyl Acetate
• CAS No.: 6186-98-7
• Molecular Formula: C20H38O2
• Molecular Weight: 310.521
• UNII: 49M29ZH9TS
• DSSTox Substance ID: DTXSID401028467
• Nikkaji Number: J1.934.560B
• Wikipedia: Vaccenyl_acetate
• Wikidata: Q6584358
• Metabolomics Workbench ID: 4032
• Mol file: 6186-98-7.mol

Synonyms:cis-Vaccenyl-acetat;3-Nonanone,1-hydroxy-,acetate;1-Hydroxy-3-nonanone acetate;3-Oxononanyl acetate;1-Acetoxy-nonan-3-on;3-Nonanon-1-yl acetate;Methylol methyl hexyl ketone acetate;1-acetoxy-3-nonanone;1-acetoxy-nonan-3-one;

Chemical Property of 11-cis Vaccenyl Acetate

Chemical Property:

• Vapor Pressure: 5.82E-06mmHg at 25°C
• Boiling Point: 379.5oC at 760 mmHg
• Flash Point: 87.8oC
• PSA: 26.30000
• Density: 0.872g/cm3
• LogP: 6.58700
• XLogP3: 7.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 17
• Exact Mass: 310.287180451
• Heavy Atom Count: 22
• Complexity: 258

Purity/Quality:

99%, ^*data from raw suppliers

11-cis-Vaccenylacetate ≥98.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC=CCCCCCCCCCCOC(=O)C
• Isomeric SMILES: CCCCCC/C=C\CCCCCCCCCCOC(=O)C
• Description: The mating and social behaviors of insects are largely orchestrated by a suite of volatile hydrocarbon pheromones. 11-cis Vaccenyl acetate is the male-specific mating pheromone of the fruit fly D. melanogaster. It acts selectively through the Or67d odorant receptor to control mating behavior in both male and female fruit flies.
• Uses: (Z)-11-Octadecenyl Acetate is a Drosophila sex pheromone.

Technology Process of 11-cis Vaccenyl Acetate

There total 25 articles about 11-cis Vaccenyl Acetate 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: 87.0%

(Z)-octadec-11-en-1-ol (62972-93-4) + acetic anhydride (108-24-7) → (Z)-11-octadecen-1-yl acetate (6186-98-7)

Guidance literature:

With pyridine; at 20 ℃; for 15h;

DOI:10.1007/BF00953115

Reference yield:

Methyl 10-undecenoate (111-81-9) → (Z)-11-octadecen-1-yl acetate (6186-98-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 95.4 percent / LAH / diethyl ether / 2 h

2: 88.7 percent / PPTS / CH₂Cl₂ / 4 h / Ambient temperature

3: 1.) diborane, 2.) PCC, sodium acetate / 1) THF, 0 deg C (2 h), RT (2 h); 2) CH₂Cl₂, reflux, 4 h

4: 78.8 percent / CH₂Cl₂ / 26 h

5: 47 percent / Li-Hg / diethyl ether / 20 h / Ambient temperature

6: 1.) n-BuLi / 1) THF; 2) HMPT, THF, below 25 deg C, 0.5 h

7: AcOH

8: H₂

With lithium aluminium tetrahydride; n-butyllithium; lithium amalgam; hydrogen; sodium acetate; pyridinium p-toluenesulfonate; acetic acid; pyridinium chlorochromate; diborane; In diethyl ether; dichloromethane;

Reference yield:

10-Undecen-1-ol (112-43-6) → (Z)-11-octadecen-1-yl acetate (6186-98-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 88.7 percent / PPTS / CH₂Cl₂ / 4 h / Ambient temperature

2: 1.) diborane, 2.) PCC, sodium acetate / 1) THF, 0 deg C (2 h), RT (2 h); 2) CH₂Cl₂, reflux, 4 h

3: 78.8 percent / CH₂Cl₂ / 26 h

4: 47 percent / Li-Hg / diethyl ether / 20 h / Ambient temperature

5: 1.) n-BuLi / 1) THF; 2) HMPT, THF, below 25 deg C, 0.5 h

6: AcOH

7: H₂

With n-butyllithium; lithium amalgam; hydrogen; sodium acetate; pyridinium p-toluenesulfonate; acetic acid; pyridinium chlorochromate; diborane; In diethyl ether; dichloromethane;

upstream raw materials:

(Z)-octadec-11-en-1-ol

acetic anhydride

octadec-11-ynyl acetate

2-(9-bromononyloxy)tetrahydropyran

Downstream raw materials:

Acetic acid 11,12-bis-methylsulfanyl-octadecyl ester

Refernces

• 1、 Ishmuratov, G. Yu.,Balezina, G. G.,Odinokov, V. N.,Zelenova, L. M.,Tolstikov, G. A.. "NEW ONE-STEP PATH FOR STEREOSPECIFIC SYNTHESIS OF (Z)-ALKEN-1-OLS FROM ACETYLENIC ALDEHYDES". . p. 609 - 610. Retrieved 2007/10/02.
• 2、 Dzhemilev, U. M.,Balezina, G. G.,Volkova, L. A.,Krivonogov, V. P.,Tolstikov, G. A.. "INSECT PHEROMONES AND THEIR ANALOGS III. SYNTHESIS OF THE SEX ATTRACTANTS OF SOME LEPIDOPTERA". . p. 82 - 85. Retrieved 2007/10/02.