(Z)-10-Pentadecenoic acid methyl ester

Base Information

• Chemical Name: (Z)-10-Pentadecenoic acid methyl ester
• CAS No.: 90176-52-6
• Molecular Formula: C16H30 O2
• Molecular Weight: 254.413
• European Community (EC) Number: 627-216-3
• Nikkaji Number: J45.031F
• Wikidata: Q63409027
• Mol file: 90176-52-6.mol

Synonyms:90176-52-6;(Z)-10-Pentadecenoic acid methyl ester;methyl (Z)-pentadec-10-enoate;Methyl cis-10-pentadecenoate;CIS-10-PENTADECENOIC ACID METHYL ESTER (C15;cis-10-Pentadecenoic acid-methyl ester;methyl 10-cis-pentadecenoate;Methyl 10(Z)-pentadecenoate;CHEBI:144350;C15:1 (cis-10) methyl ester;METHYL (Z)-10-PENTADECENOATE;10(Z)-pentadecenoic acid methyl ester;cis-10-Pentadecenoic acid methyl ester;PD094732;METHYL (10Z)-PENTADEC-10-ENOATE;cis-10-Pentadecenoic acid methyl ester(c15:1);Q63409027;10-Pentadecenoic acid, methyl ester, (Z)-;Methyl Z-10-pentadecenoate

Chemical Property of (Z)-10-Pentadecenoic acid methyl ester

Chemical Property:

• Boiling Point: 320.9±11.0 °C(Predicted)
• PSA: 26.30000
• Density: 0.878±0.06 g/cm3(Predicted)
• LogP: 5.02660
• Storage Temp.: −20°C
• XLogP3: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 13
• Exact Mass: 254.224580195
• Heavy Atom Count: 18
• Complexity: 209

Purity/Quality:

NLT 98% ^*data from raw suppliers

10(Z)-Pentadecenoic Acid methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC=CCCCCCCCCC(=O)OC
• Isomeric SMILES: CCCC/C=C\CCCCCCCCC(=O)OC

Technology Process of (Z)-10-Pentadecenoic acid methyl ester

There total 10 articles about (Z)-10-Pentadecenoic acid methyl ester 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: 50.0%

10-oxo-decanoic acid methyl ester (14811-73-5) + pentyltriphenylphosphonium bromide (21406-61-1) → cis-10-pentadecenoic acid methyl ester (90176-52-6)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; 1. 1h reflux 2. -78 deg C, 1h 3. 25 deg C, 20h;

DOI:10.1016/S0040-4039(01)81267-3

Reference yield:

10-oxo-decanoic acid methyl ester (14811-73-5) + pentylidenetriphenylphosphorane (29541-98-8,55317-64-1) → cis-10-pentadecenoic acid methyl ester (90176-52-6) + Methyl Z 10-pentadecenoate (90176-51-5)

Guidance literature:

With sodium ethanolate; In toluene; at 25 ℃; for 2h; Yield given. Yields of byproduct given;

Reference yield:

10,11-dihydroxyundecanoic acid (32779-22-9) → cis-10-pentadecenoic acid methyl ester (90176-52-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / methanol / 4 h / Heating

2: 90 percent / lead(IV)-acetate / benzene / 12 h / 25 °C

3: 50 percent / 1. NaHMDS / tetrahydrofuran / 1. 1h reflux 2. -78 deg C, 1h 3. 25 deg C, 20h

With lead(IV) acetate; sodium hexamethyldisilazane; In tetrahydrofuran; methanol; benzene;

DOI:10.1016/S0040-4039(01)81267-3

upstream raw materials:

10-oxo-decanoic acid methyl ester

pentylidenetriphenylphosphorane

n-pentyltriphenylphosphonium iodide

pentyltriphenylphosphonium bromide

Downstream raw materials:

(10Z)-10-pentadecen-1-ol

(3Z,13Z)-3,13-octadecadien-1-yl acetate

10(Z)-pentadecen-1-yltriphenylphosphonium bromide

(3E, 13Z)-3,13-octadecadien-1-yl acetate

Refernces

• 1、 Vinczer, Peter,Juvancz, Zoltan,Novak, Lajos,Szantay, Csaba. "SYNTHESIS OF PHEROMONES, IV. CHEMISTRY OF THE WITTIG REACTION, I. EFFECTS OF REACTION CONDITIONS ON THE STEREOSELECTIVITY AND YIELD OF THE WITTIG REACTION". . p. 797 - 820. Retrieved 2007/10/02.
• 2、 Vinczer, Peter,Baan, Gabor,Novak, Lajos,Szantay, Csaba. "A NOVEL STEREOCONTROLLED SYNTHESIS OF (Z,Z)-3,13-OCTADECDIEN-1-YL ACETATE, THE SEX PHEROMONE OF SYNANTHEDON SPECIES". . p. 2701 - 2704. Retrieved 2007/10/02.