(2E,13Z)-2,13-Octadecadienol

Base Information

• Chemical Name: (2E,13Z)-2,13-Octadecadienol
• CAS No.: 123551-47-3
• Molecular Formula: C18H34O
• Molecular Weight: 266.462
• UNII: ACH085LK6R
• DSSTox Substance ID: DTXSID7057577
• Nikkaji Number: J2.705.569I
• Metabolomics Workbench ID: 3150
• Mol file: 123551-47-3.mol

Synonyms:123551-47-3;(2E,13Z)-2,13-Octadecadienol;(2E,13Z)-Octadecadien-1-ol;(E,Z)-2,13-OCTADECADIENOL;(2E,13Z)-octadeca-2,13-dien-1-ol;2,13-Octadecadien-1-ol, (2E,13Z)-;(E,Z)-2,13-Octadecadien-1-ol;UNII-ACH085LK6R;ACH085LK6R;2E,13Z-octadecadien-1-ol;octadecan-2E,13Z-dien-1-ol;LMFA05000057;Octadeca-2,13-dien-1-ol;SCHEMBL1300680;DTXSID7057577;E,Z-2,13-Octadecadien-1-ol;YCOMGIOWVNOOBC-RAPDCGKPSA-N;AMY14967;FD7215;AKOS025213454;(2E,13Z)-2,13-Octadecadien-1-ol;(2E,13Z)-2,13-Octadecadiene-1-ol;(2E,13Z)-2,13-Octadecadien-1-ol #;(2E,13Z)-Octadecadien-1-ol CAS 123551-47-3;Q27273867

Chemical Property of (2E,13Z)-2,13-Octadecadienol

Chemical Property:

• Refractive Index: 1.4694 (20℃)
• Boiling Point: 363.7 °C at 760 mmHg
• PKA: 14.44±0.10(Predicted)
• Flash Point: 118.4 °C
• PSA: 20.23000
• Density: 0.858 g/cm³
• LogP: 5.79220
• XLogP3: 7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 14
• Exact Mass: 266.260965704
• Heavy Atom Count: 19
• Complexity: 206

Purity/Quality:

99%, ^*data from raw suppliers

(2E,13Z)-Octadecadien-1-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC=CCCCCCCCCCC=CCO
• Isomeric SMILES: CCCC/C=C\CCCCCCCCC/C=C/CO
• Uses: Sex phermone produced by the female hornet moth, Sesia apiformis.

Technology Process of (2E,13Z)-2,13-Octadecadienol

There total 54 articles about (2E,13Z)-2,13-Octadecadienol 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: 99.3%

octadec-cis-13-en-2-yne-1-ol (123551-46-2) → (2E,13Z)-2,13-octadecadien-1-ol (123551-47-3)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; toluene; for 48h; Ambient temperature;

Reference yield: 98.0%

E-2-octadecen-13-yn-1-ol (150047-50-0) → (2E,13Z)-2,13-octadecadien-1-ol (123551-47-3)

Guidance literature:

With quinoline; hydrogen; Pd-BaSO₄; In hexane; for 4h; Ambient temperature;

Reference yield: 97.0%

ethyl ester trans-2,cis-13-octadecadienoic acid (118971-63-4) → (2E,13Z)-2,13-octadecadien-1-ol (123551-47-3)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 2h; Inert atmosphere;

DOI:10.1002/anie.201700342

upstream raw materials:

octadec-cis-13-en-2-yne-1-ol

ethyl ester trans-2,cis-13-octadecadienoic acid

E-2-octadecen-13-yn-1-ol

1-bromo-dec-5c-ene

Downstream raw materials:

(2E,13Z)-2,13-octadecadienal

(2E,13Z)-octadeca-2,13-dienyl acetate

Refernces

• 1、 Sorochinskaya, A. M.,Kovalev, B. G.. "SYNTHESIS OF THE ACETATE OF OCTADECA-trans-2,cis-13-DIEN-1-OL, A COMPONENT OF THE SEX PHEROMONES OF synanthedon tipuliformis AND Zeuzera pyrina". . p. 228 - 230. Retrieved 1989.
• 2、 Rummelt, Stephan M.,Cheng, Gui-Juan,Gupta, Puneet,Thiel, Walter,Fürstner, Alois. "Hydroxy-Directed Ruthenium-Catalyzed Alkene/Alkyne Coupling: Increased Scope, Stereochemical Implications, and Mechanistic Rationale". supporting information. p. 3599 - 3604. Retrieved 2017/03/21.
• 3、 Ishmuratov,Botsman,Botsman,Yakovleva,Kharisov,Tolstikov. "Synthesis from 10-undecenoic acid of octadeca-2E,13Z-dienylacetate, a component of the sex pheromones of Synanthedon tipuliformis and Zenzera pyrina". . p. 207 - 209. Retrieved 2007/10/03.