15-Hydroxyhexadecanoic acid methyl ester

Base Information

• Chemical Name: 15-Hydroxyhexadecanoic acid methyl ester
• CAS No.: 55823-13-7
• Molecular Formula: C₁₇H₃₄O₃
• Molecular Weight: 286.455
• Mol file: 55823-13-7.mol

Synonyms:15-Hydroxyhexadecanoic acid methyl ester

Chemical Property of 15-Hydroxyhexadecanoic acid methyl ester

Chemical Property:

• Melting Point: 55.0-56.0 °C
• Boiling Point: 370.4±15.0 °C(Predicted)
• PKA: 15.26±0.20(Predicted)
• PSA: 46.53000
• Density: 0.922±0.06 g/cm3(Predicted)
• LogP: 4.61150

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 15-Hydroxyhexadecanoic acid methyl ester

There total 19 articles about 15-Hydroxyhexadecanoic 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: 84.0%

methyl 15-benzyloxyhexadec-2-enoate → 15-hydroxyhexadecanoic acid methyl ester (55823-13-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; hexane; under 760 Torr;

DOI:10.1021/ol035254e

Reference yield:

10-Undecenal (112-45-8) → 15-hydroxyhexadecanoic acid methyl ester (55823-13-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 100 percent / diethyl ether / -40 °C

2.1: 95 percent / NaH; tetra-t-butylammonium iodide / tetrahydrofuran; diethyl ether / 48 h / 20 °C

3.1: BH₃*SMe₂ / CH₂Cl₂; tetrahydrofuran / Heating

3.2: 67 percent / NaOH; H₂O₂ / CH₂Cl₂; tetrahydrofuran; H₂O

4.1: 93 percent / sodium acetate; PCC / CH₂Cl₂

5.1: 84 percent / CHCl₃ / 12 h / Heating

6.1: 90 percent / LiAlH₄ / tetrahydrofuran / 12 h / 0 °C

7.1: PCC / CH₂Cl₂ / 6 h

8.1: 0.330 g / CHCl₃ / 12 h / Heating

9.1: 84 percent / H₂ / Pd/C / methanol; hexane / 760 Torr

With lithium aluminium tetrahydride; dimethylsulfide borane complex; hydrogen; sodium acetate; tetra(tert-butyl)ammonium iodide; sodium hydride; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; 1.1: Grignard reaction;

DOI:10.1021/ol035254e

Reference yield:

10-Undecen-1-ol (112-43-6) → 15-hydroxyhexadecanoic acid methyl ester (55823-13-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 84 percent / PCC; sodium acetate / CH₂Cl₂

2.1: 100 percent / diethyl ether / -40 °C

3.1: 95 percent / NaH; tetra-t-butylammonium iodide / tetrahydrofuran; diethyl ether / 48 h / 20 °C

4.1: BH₃*SMe₂ / CH₂Cl₂; tetrahydrofuran / Heating

4.2: 67 percent / NaOH; H₂O₂ / CH₂Cl₂; tetrahydrofuran; H₂O

5.1: 93 percent / sodium acetate; PCC / CH₂Cl₂

6.1: 84 percent / CHCl₃ / 12 h / Heating

7.1: 90 percent / LiAlH₄ / tetrahydrofuran / 12 h / 0 °C

8.1: PCC / CH₂Cl₂ / 6 h

9.1: 0.330 g / CHCl₃ / 12 h / Heating

10.1: 84 percent / H₂ / Pd/C / methanol; hexane / 760 Torr

With lithium aluminium tetrahydride; dimethylsulfide borane complex; hydrogen; sodium acetate; tetra(tert-butyl)ammonium iodide; sodium hydride; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; 2.1: Grignard reaction;

DOI:10.1021/ol035254e

upstream raw materials:

diazomethane

hexadecan-2-one

methanol

hexadecyl methyl ether

Downstream raw materials:

15-hydroxypalmitate methyl ester silyl ether

Refernces

• 1、 Cryle, Max J.,De Voss, James J.. "Facile determination of the absolute stereochemistry of hydroxy fatty acids by GC: application to the analysis of fatty acid oxidation by a P450BM3 mutant". . p. 547 - 551. Retrieved 2007/10/03.
• 2、 Jones,Howe. "Microbiological oxidation of long-chain aliphatic compounds. 3. 1-halogenoalkenes, 1-cyanohexadecane, and 1-alkoxyalkanes.". . p. 2816 - 2821. Retrieved 2007/10/05.