Methyl 17-hydroxyheptadecanoate

Base Information

• Chemical Name: Methyl 17-hydroxyheptadecanoate
• CAS No.: 94036-00-7
• Molecular Formula: C18H36O3
• Molecular Weight: 300.482
• ChEMBL ID: CHEMBL477885
• DSSTox Substance ID: DTXSID50531632
• Metabolomics Workbench ID: 137721
• Nikkaji Number: J297.383I
• Wikidata: Q82403634
• Mol file: 94036-00-7.mol

Synonyms:METHYL 17-HYDROXYHEPTADECANOATE;94036-00-7;Heptadecanoic acid, 17-hydroxy-, methyl ester;CHEMBL477885;SCHEMBL3502658;methyl 17-hydroxy heptadecanoate;methyl omega-hydroxyheptadecanoate;DTXSID50531632;omega-Hydroxy C17:0 methyl ester;PD077324

Chemical Property of Methyl 17-hydroxyheptadecanoate

Chemical Property:

• PSA: 46.53000
• LogP: 5.00320
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 17
• Exact Mass: 300.26644501
• Heavy Atom Count: 21
• Complexity: 217

Purity/Quality:

98% ^*data from raw suppliers

17-hydroxy Heptadecanoic Acid methyl ester ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCCCCCCCCCCCCCCCO

Technology Process of Methyl 17-hydroxyheptadecanoate

There total 10 articles about Methyl 17-hydroxyheptadecanoate 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: 85.6%

heptadecanedioic acid monomethyl ester (72849-42-4) → 17-hydroxy-heptadecanoic acid methyl ester (94036-00-7)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃; for 12h; Inert atmosphere;

Reference yield:

15-(acryloyloxy)pentadecanoic acid (1190441-70-3) → 17-hydroxy-heptadecanoic acid methyl ester (94036-00-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide; terephthalonitrile; phenanthrene / acetonitrile; water / 6 h / 20 °C / Inert atmosphere; UV-irradiation

2.1: potassium hydroxide / ethanol / 2 h / Reflux

2.2: 0 - 20 °C / Inert atmosphere

With terephthalonitrile; phenanthrene; potassium hydroxide; sodium hydroxide; In ethanol; water; acetonitrile;

DOI:10.1021/jo3024126

Reference yield:

pentadecanolide (106-02-5,81031-90-5) → 17-hydroxy-heptadecanoic acid methyl ester (94036-00-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium hydroxide / ethanol / 2 h / Reflux

2.1: pyridine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: magnesium bromide ethyl etherate / diethyl ether / 2 h / 20 °C

5.1: sodium hydroxide; terephthalonitrile; phenanthrene / acetonitrile; water / 6 h / 20 °C / Inert atmosphere; UV-irradiation

6.1: potassium hydroxide / ethanol / 2 h / Reflux

6.2: 0 - 20 °C / Inert atmosphere

With pyridine; terephthalonitrile; phenanthrene; magnesium bromide ethyl etherate; triethylamine; potassium hydroxide; sodium hydroxide; In diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo3024126

upstream raw materials:

methanol

17-hydroxy-heptadecanoic acid

15-(acryloyloxy)pentadecanoic acid

pentadecanolide

Refernces

• 1、 Nishikawa, Keisuke,Yoshimi, Yasuharu,Maeda, Kousuke,Morita, Toshio,Takahashi, Ichiro,Itou, Tatsuya,Inagaki, Sho,Hatanaka, Minoru. "Radical photocyclization route for macrocyclic lactone ring expansion and conversion to macrocyclic lactams and ketones". . p. 582 - 589. Retrieved 2013/03/13.