(Z)-13-Octadecenal

Base Information

• Chemical Name: (Z)-13-Octadecenal
• CAS No.: 58594-45-9
• Molecular Formula: C18H34O
• Molecular Weight: 266.467
• European Community (EC) Number: 261-349-4
• UNII: FJA253248W
• DSSTox Substance ID: DTXSID2035774
• Nikkaji Number: J726I
• Metabolomics Workbench ID: 3630
• Mol file: 58594-45-9.mol

Synonyms:(Z)-13-Octadecenal;58594-45-9;(Z)-octadec-13-enal;13-Octadecenal, (Z)-;13Z-Octadecenal;13-Octadecenal, (13Z)-;UNII-FJA253248W;FJA253248W;Z-13-Octadecanal;EINECS 261-349-4;cis-13-Octadecenal;13Z-Octadecanal;(13Z)-13-Octadecenal;Z-13-Octadecenal;(13Z)-octadec-13-enal;SCHEMBL811956;(13Z)-13-Octadecenal #;DTXSID2035774;OCTADECENAL, (Z)-13-;QIRGIHPYVVKWTO-WAYWQWQTSA-N;LMFA06000237;Q27278021

Chemical Property of (Z)-13-Octadecenal

Chemical Property:

• Appearance/Colour: colorless to yellow liquid
• Vapor Pressure: 3E-05mmHg at 25°C
• Refractive Index: 1.453
• Boiling Point: 356 °C at 760 mmHg
• Flash Point: 179.2 °C
• PSA: 17.07000
• Density: 0.841 g/cm³
• LogP: 6.22280
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 15
• Exact Mass: 266.260965704
• Heavy Atom Count: 19
• Complexity: 196

Purity/Quality:

98%,99%, ^*data from raw suppliers

(Z)-13-Octadecenal ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC=CCCCCCCCCCCCC=O
• Isomeric SMILES: CCCC/C=C\CCCCCCCCCCCC=O
• Uses: (Z)-13-Octadecenal is a sex pheromone component of the rice stem borer Chilo suppressalis (Lepidoptera).

Technology Process of (Z)-13-Octadecenal

There total 21 articles about (Z)-13-Octadecenal 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: 95.0%

C19H36O → (Z)-13-octadecenal (58594-45-9,56554-90-6,69820-24-2)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; at 55 ℃; for 10h;

Reference yield: 75.0%

(Z)-octadec-13-en-1-ol (69820-27-5) → (Z)-13-octadecenal (58594-45-9,56554-90-6,69820-24-2)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 3h;

DOI:10.5012/bkcs.2011.32.8.3120

Reference yield:

1-tetrahydropyranyloxy-13-(Z)-octadecene (130253-49-5) → (Z)-13-octadecenal (58594-45-9,56554-90-6,69820-24-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / pyridinium p-toluenesulfonate / methanol / 6 h / 55 °C

2: 60 percent / pyridinium dichromate / CH₂Cl₂ / 24 h

With dipyridinium dichromate; pyridinium p-toluenesulfonate; In methanol; dichloromethane;

upstream raw materials:

(Z)-octadec-13-en-1-ol

4-(Z)-nonenemagnesium bromide

1-tetrahydropyranyloxy-13-(Z)-octadecene

methyl cis-13-docosenoate

Downstream raw materials:

(Z)-octadec-13-en-1-ol

Refernces

• 1、 -. "Preparation method of rice borer pheromone component". Paragraph 0061; 0074; 0075. . Retrieved 2019/05/15.
• 2、 Trehan,Vig,Singh,Sharma,Kad. "Stereospecific syntheses of a few Lepidoptera pheromones containing (Z)-alkene moiety". . p. 518 - 520. Retrieved 2007/10/02.