Methyl 15-hydroxypentadecanoate

Base Information

• Chemical Name: Methyl 15-hydroxypentadecanoate
• CAS No.: 76529-42-5
• Molecular Formula: C16H32O3
• Molecular Weight: 272.428
• DSSTox Substance ID: DTXSID40393044
• Nikkaji Number: J297.407J
• Wikidata: Q82191651
• Metabolomics Workbench ID: 137722
• ChEMBL ID: CHEMBL477886
• Mol file: 76529-42-5.mol

Synonyms:methyl 15-hydroxypentadecanoate;76529-42-5;Pentadecanoic acid, 15-hydroxy-, methyl ester;CHEMBL477886;SCHEMBL1976107;methyl omega-hydroxypentadecanoate;DTXSID40393044;WQCYAHKAJFZVCO-UHFFFAOYSA-N;BDA52942;15-hydroxypentadecanoic acid methyl ester;Methyl 15-Hydroxypentadecanoate, (C15);PD077419;CS-0331113;A902740

Chemical Property of Methyl 15-hydroxypentadecanoate

Chemical Property:

• Melting Point: 47.0-48.0 °C
• Boiling Point: 359.5±15.0 °C(Predicted)
• PKA: 15.20±0.10(Predicted)
• PSA: 46.53000
• Density: 0.927±0.06 g/cm3(Predicted)
• LogP: 4.22300
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 272.23514488
• Heavy Atom Count: 19
• Complexity: 192

Purity/Quality:

97% ^*data from raw suppliers

Methyl15-hydroxypentadecanoate 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCCCCCCCCCCCCCO
• Description: 15-hydroxy Pentadecanoic acid methyl ester is a hydroxylated fatty acid methyl ester that is a key intermediate in the synthesis of the musk-odored macrocyclic lactones cyclopentadecanolide and exaltolide. [Matreya, LLC. Catalog No. 1882]

Technology Process of Methyl 15-hydroxypentadecanoate

There total 20 articles about Methyl 15-hydroxypentadecanoate 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: 100.0%

methanol (67-56-1) + pentadecanolide (106-02-5,81031-90-5) → methyl 15-hydroxypentadecanoate (76529-42-5)

Guidance literature:

With sulfuric acid; Reflux;

DOI:10.1016/j.tetlet.2016.12.040

Reference yield: 99.0%

pentadecanolide (106-02-5,81031-90-5) + sodium methylate (124-41-4) → methyl 15-hydroxypentadecanoate (76529-42-5)

Guidance literature:

In methanol; at 20 ℃; for 16h; Inert atmosphere; Darkness;

DOI:10.1039/c6cc09305a

Reference yield: 98.0%

methanol (67-56-1) + pentadecanolide (106-02-5,81031-90-5) + sodium methylate (124-41-4) → methyl 15-hydroxypentadecanoate (76529-42-5)

Guidance literature:

for 3h; Heating / reflux;

upstream raw materials:

methanol

15-hydroxylpentadecanoic acid

15-oxo-pentadecanoic acid methyl ester

pentadecane

Downstream raw materials:

15-hydroxylpentadecanoic acid

15-hydroxy-pentadecanoic acid hydrazide

methyl 15-((tert-butyldiphenylsilyl)oxy)pentadecanoate

15-(1-phenyl-1H-tetrazole-5-sulfonyl)pentadecanoic acid methyl ester

Refernces

• 1、 Taher, Salam G.,Al Dulayymi, Juma'a R.,Tima, H. Giresse,Ali, Hanan M.,Romano, Marta,Baird, Mark S.. "Synthesis of wax esters and related trehalose esters from Mycobacterium avium and other mycobacteria". . p. 3863 - 3876. Retrieved 2016.
• 2、 Defretin, Julie,Saez, Jairo,Franck, Xavier,Hocquemiller, Reynald,Figadere, Bruno. "Stereoselective synthesis of unsaturated very long chain fatty acid methyl esters". . p. 4041 - 4044. Retrieved 1999.
• 3、 Guttenberger, Nikolaus,Sagmeister, Peter,Glabonjat, Ronald A.,Hirner, Stefan,Francesconi, Kevin A.. "Facile access to arsenic-containing triacylglycerides". supporting information. p. 362 - 364. Retrieved 2017/01/03.
• 4、 Ng, Cheng Yang,Kwok, Timothy Xiong Wei,Tan, Francis Chee Kuan,Low, Chian-Ming,Lam, Yulin. "Fluorogenic probes to monitor cytosolic phospholipase A2 activity". supporting information. p. 1813 - 1816. Retrieved 2017/02/10.