METHYL 2-HYDROXYHEXADECANOATE

Base Information

• Chemical Name: METHYL 2-HYDROXYHEXADECANOATE
• CAS No.: 16742-51-1
• Molecular Formula: C17H34O3
• Molecular Weight: 286.455
• Hs Code.: 2918199090
• Mol file: 16742-51-1.mol

Synonyms:Palmiticacid, a-hydroxy-, methyl ester (4CI);(?à)-Methyl 2-Hydroxyhexadecanoate;Methyl 2-hydroxyhexadecanoate;Methyl a-hydroxypalmitate;Dl-A-hydroxypalmitic acid methyl ester;

Chemical Property of METHYL 2-HYDROXYHEXADECANOATE

Chemical Property:

• Vapor Pressure: 1.26E-05mmHg at 25°C
• Refractive Index: 1.453
• Boiling Point: 330 °C at 760 mmHg
• Flash Point: 147.1 °C
• PSA: 46.53000
• Density: 0.922 g/cm³
• LogP: 4.61150
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

2-hydroxy Palmitic Acid methyl ester ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of METHYL 2-HYDROXYHEXADECANOATE

There total 50 articles about METHYL 2-HYDROXYHEXADECANOATE 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: 93.0%

methyl 2-oxo-hexadecanoate (55836-30-1) → methyl (R)-2-hydroxyhexadecanoate (16742-51-1,78330-57-1,89301-98-4,36451-47-5)

Guidance literature:

With formic acid; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 3,3'-[(1R,2R)-1-amino-2-(4-dodecylphenylsulfonamido)ethane-1,2-diyl]bis(N,N,N-trimethylbenzenaminium)diiodide; sodium formate; In water; at 25 ℃; for 6h; enantioselective reaction;

DOI:10.1021/acs.joc.5b00241

Reference yield: 78.0%

methanol (67-56-1) + 1-O-β-D-glucopyranosyl-(2S,3R,5E,12E)-2N-[(2R)-hydroxyhexadecanoyl]-octadecasphinga-5,12-dienine (1356390-80-1) → methyl (R)-2-hydroxyhexadecanoate (16742-51-1,78330-57-1,89301-98-4,36451-47-5) + 1-O-β-D-glucopyranosylsphingosine (1356390-82-3)

Guidance literature:

With hydrogenchloride; at 60 ℃; for 15h;

Reference yield: 70.0%

1-iodotridecane (35599-77-0) + methyl (2R)-glycidate (4538-50-5,85485-00-3,118712-39-3,111058-32-3) → methyl (R)-2-hydroxyhexadecanoate (16742-51-1,78330-57-1,89301-98-4,36451-47-5)

Guidance literature:

1-iodotridecane; With tert.-butyl lithium; In diethyl ether; pentane; at -78 - 20 ℃; Inert atmosphere;

With copper(I) bromide dimethylsulfide complex; dimethylsulfide; In diethyl ether; pentane; at 0 ℃; for 1h; Inert atmosphere;

methyl (2R)-glycidate; In diethyl ether; pentane; at -78 - -60 ℃; Inert atmosphere;

DOI:10.1039/b920285d

upstream raw materials:

methanol

(R)-(-)-2-hydroxyhexadecanoic acid

dimethyl sulfate

diazomethane

Downstream raw materials:

(2R)-(+)-1,2-hexadecanediol

methyl (R)-2-hydroxyhexadecanoate

methyl (2S)-2-O-acetyl hexadecanoate

methyl (2R)-2-O-acetyl hexadecanoate

Refernces

• 1、 Ahn, Young Min,Lee, Won-Woong,Jung, Jee H.,Lee, Sang-Gi,Honga, Jongki. "Structural determination of glucosylceramides isolated from marine sponge by fast atom bombardment collision-induced dissociation linked scan at constant B/E". . p. 1698 - 1708. Retrieved 2009.
• 2、 Abdelhameed, Reda F.A.,Eltamany, Enas E.,Hal, Dina M.,Ibrahim, Amany K.,AboulMagd, Asmaa M.,Al-Warhi, Tarfah,Youssif, Khayrya A.,Abd El-Kader, Adel M.,Hassanean, Hashim A.,Fayez, Shaimaa,Bringmann, Gerhard,Ahmed, Safwat A.,Abdelmohsen, Usama Ramadan. "New cytotoxic cerebrosides from the red sea cucumber Holothuria spinifera supported by in-silico studies". . . Retrieved 2020/09/07.
• 3、 Lin, Zechao,Li, Jiahong,Huang, Qingfei,Huang, Qiuya,Wang, Qiwei,Tang, Lei,Gong, Deying,Yang, Jun,Zhu, Jin,Deng, Jingen. "Chiral Surfactant-Type Catalyst: Enantioselective Reduction of Long-Chain Aliphatic Ketoesters in Water". . p. 4419 - 4429. Retrieved 2015/05/13.