Glyceryl monolinoleate

Base Information

• Chemical Name: Glyceryl monolinoleate
• CAS No.: 2277-28-3
• Deprecated CAS: 127961-15-3,100786-09-2
• Molecular Formula: C21H38 O4
• Molecular Weight: 354.524
• Hs Code.: 2916190090
• European Community (EC) Number: 247-788-4,218-901-4
• UNII: MGG581HK1Y
• DSSTox Substance ID: DTXSID201016719
• Nikkaji Number: J116.896G
• Wikidata: Q27881752
• RXCUI: 1368193
• Metabolomics Workbench ID: 5769
• ChEMBL ID: CHEMBL458250
• Mol file: 2277-28-3.mol

Synonyms:1-monolinoleoyl-rac-glycerol;glyceryl linoleic acid monoester;mLG cpd;monolinolein

Chemical Property of Glyceryl monolinoleate

Chemical Property:

• Appearance/Colour: Colourless Oil
• Vapor Pressure: 1.91E-11mmHg at 25°C
• Melting Point: 14-15 °C
• Refractive Index: 1.488
• Boiling Point: 485 °C at 760 mmHg
• PKA: 13.16±0.20(Predicted)
• Flash Point: 157 °C
• PSA: 66.76000
• Density: 0.981 g/cm³
• LogP: 4.69630
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 18
• Exact Mass: 354.27700969
• Heavy Atom Count: 25
• Complexity: 350

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Linoleoyl-rac-glycerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CCCCCCCCC(=O)OCC(CO)O
• Isomeric SMILES: CCCCC/C=C\C/C=C\CCCCCCCC(=O)OCC(CO)O
• Uses: 1-Linoleyl glyceride as free-living amoeba control agent; also a biomarker of metabolic responses to hepatotoxicants and carcinogens. glyceryl linoleate is an emollient with moisturizing capabilities. It is synthetically produced from naturally derived ingredients.

Technology Process of Glyceryl monolinoleate

There total 17 articles about Glyceryl monolinoleate 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: 95.0%

Methyl linoleate (112-63-0) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → 1-monolinoleoyl-rac-glycerol (2258-92-6,2277-28-3,67968-46-1,107380-08-5,126455-47-8,126455-48-9)

Guidance literature:

Methyl linoleate; glycerol; at 150 ℃; for 20h; under 60.006 Torr;

With sodium ethanolate; for 0.5h; under 0.750075 Torr;

Reference yield: 79.0%

vinyl linoleate (3234-56-8) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → 1-monolinoleoyl-rac-glycerol (2258-92-6,2277-28-3,67968-46-1,107380-08-5,126455-47-8,126455-48-9)

Guidance literature:

With tert-butyl methyl ether; lipase from Rhizopus niveus; silica gel; for 144h; Ambient temperature;

DOI:10.1007/BF02523518

Reference yield: 78.0%

(+/-)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl (9Z,12Z)-9,12-octadecadienoate (127592-95-4) → 1-monolinoleoyl-rac-glycerol (2258-92-6,2277-28-3,67968-46-1,107380-08-5,126455-47-8,126455-48-9)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran;

upstream raw materials:

linoleyl chloride

glycerol

(+/-)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl (9Z,12Z)-9,12-octadecadienoate

vinyl linoleate

Downstream raw materials:

α-Linoleoyl-β,α'-distearoin

1,2-dihexadecanoyl-3-(9,12-octadecadienoyl)glycerol

1,3-dihexadecanoyl-2-(9,12-octadecadienoyl)glycerol

trans-1,3-dilinolein

Refernces

• 1、 -. "IONIZABLE AMINE LIPIDS AND LIPID NANOPARTICLES". Page/Page column 87-89; 168. . Retrieved 2020/11/04.
• 2、 Mori, Kenji. "Pheromone synthesis. Part 253: Synthesis of the racemates and enantiomers of triglycerides of male Drosophila fruit flies with special emphasis on the preparation of enantiomerically pure 1-monoglycerides". experimental part. p. 8441 - 8449. Retrieved 2012/10/07.