Glyceryl monooleate

Base Information

• Chemical Name: Glyceryl monooleate
• CAS No.: 111-03-5
• Deprecated CAS: 30836-40-9,33978-07-3,925-14-4,117628-77-0,125622-45-9,1330-82-1,143519-87-3,148507-38-4,66676-57-1,95917-02-5,206072-75-5,586953-12-0,925-14-4
• Molecular Formula: C21H40O4
• Molecular Weight: 356.54
• Hs Code.: 29161500
• European Community (EC) Number: 203-827-7,247-038-6,266-951-0
• NSC Number: 406285
• UNII: D3AEF6S35P
• DSSTox Substance ID: DTXSID3042003
• Nikkaji Number: J5.104G
• Wikidata: Q27071132
• NCI Thesaurus Code: C77467
• RXCUI: 1311678
• Pharos Ligand ID: H3HQBG5P7B8S
• Metabolomics Workbench ID: 5768
• ChEMBL ID: CHEMBL428593
• Mol file: 111-03-5.mol

Synonyms:1-oleoyl monoglyceride;1-oleoyl-2-glycerol;glycerol monooleate;glyceryl monooleate;glycerylmonooleate;mono-oleoylglycerol;monoelaidin;monolein;monoolein;myverol 18-99;oleic acid monoglyceride;sn-1-O-(cis-9)octadecenylglycerol

Chemical Property of Glyceryl monooleate

Chemical Property:

• Melting Point: 35-37 °C
• Refractive Index: 1.46384 (589.3 nm 35℃)
• Boiling Point: 483.3 °C at 760 mmHg
• PKA: 13.16±0.20(Predicted)
• Flash Point: 155.4 °C
• PSA: 66.76000
• Density: 0.969 g/cm³
• LogP: 4.92030
• Storage Temp.: −20°C
• Solubility.: chloroform: 50 mg/mL, clear, colorless
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 19
• Exact Mass: 356.29265975
• Heavy Atom Count: 25
• Complexity: 315

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): F, Xn
• Hazard Codes: F,Xn
• Statements: 11-20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: UVCB,Other Uses -> Emulsifiers/Surfactants
• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)OCC(CO)O
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OCC(CO)O
• Uses: Monoglycerides fatty acid esters 93% 1-Oleoyl, 7% 2-oleoyl. glyceryl oleate is an emollient and stabilizer derived from olive oil. It is a water-in-oil emulsifier that allows for softer emulsions than glyceryl stearate. Glyceryl Monooleate is a flavoring agent that is prepared by esterification of commercial oleic acid that is derived either from edible sources or from tall oil fatty acids. It contains and glyceryl esters of fatty acids present in commercial oleic acid. The ingredient is also used as an adjuvant and as a solvent and vehicle.

Technology Process of Glyceryl monooleate

There total 45 articles about Glyceryl monooleate 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: 96.2%

(+/-)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl (Z)-9-octadecenoate (33001-45-5,34487-29-1,69483-89-2,115268-49-0,150447-02-2) → 1-monooleoyl glycerol (111-03-5,2716-53-2,30836-40-9,34487-30-4,69483-90-5,99297-71-9,129784-87-8,33978-07-3,925-14-4)

Guidance literature:

With Dowex H⁺ resin; In methanol; at 20 ℃;

DOI:10.1039/c6ra28100a

Reference yield: 91.5%

4-hydroxymethyl-1,3-dioxolan-2-one (931-40-8) + cis-Octadecenoic acid (112-80-1,2027-47-6) → 1-monooleoyl glycerol (111-03-5,2716-53-2,30836-40-9,34487-30-4,69483-90-5,99297-71-9,129784-87-8,33978-07-3,925-14-4)

Guidance literature:

With triethylamine; at 140 ℃; for 9h;

DOI:10.1007/s11746-007-1091-z

Reference yield: 88.9%

cis-Octadecenoic acid (112-80-1,2027-47-6) + 3-monochloro-1,2-propanediol (96-24-2) → 1-monooleoyl glycerol (111-03-5,2716-53-2,30836-40-9,34487-30-4,69483-90-5,99297-71-9,129784-87-8,33978-07-3,925-14-4)

Guidance literature:

With N,N,N',N'-tetramethylguanidine; In N,N-dimethyl-formamide; at 80 ℃; for 12h;

upstream raw materials:

Methyl oleate

cis-Octadecenoic acid

glycerol

(Z)-9-octadecenoyl chloride

Downstream raw materials:

1,2-bis-lauroyloxy-3-oleoyloxy-propane

(+/-)-1,2-bis-octadeca-9c,11t,13t-trienoyloxy-3-oleoyloxy-propane

1,3-diolein

2-Oleoylglycerol

Refernces

• 1、 Nakajima, Nobuyoshi,Sugimoto, Manabu,Tsuboi, Sadao,Tsuji, Hideaki,Ishihara, Kohji. "An isozyme of earthworm serine proteases acts on hydrolysis of triacylglycerol". . p. 2009 - 2011. Retrieved 2005.
• 2、 Quinn,Jensen. "". . p. 692. Retrieved 1971.
• 3、 Ghandi, Mehdi,Mostashari, Abdoljalil,Karegar, Mojgan,Barzegar, Mina. "Efficient synthesis of α-monoglycerides via solventless condensation of fatty acids with glycerol carbonate". . p. 681 - 685. Retrieved 2007.
• 4、 Sikwal, Dhiraj R.,Kalhapure, Rahul S.,Jadhav, Mahantesh,Rambharose, Sanjeev,Mocktar, Chunderika,Govender, Thirumala. "Non-ionic self-assembling amphiphilic polyester dendrimers as new drug delivery excipients". . p. 14233 - 14246. Retrieved 2017.
• 5、 Lozano, Pedro,Gomez, Celia,Nieto, Susana,Sanchez-Gomez, Gregorio,García-Verdugo, Eduardo,Luis, Santiago V.. "Highly selective biocatalytic synthesis of monoacylglycerides in sponge-like ionic liquids". . p. 390 - 396. Retrieved 2017.
• 6、 -. "High-selectivity synthesis method of long-chain fatty acid monoglyceride". Paragraph 0047; 0050. . Retrieved 2019/02/27.
• 7、 Joshi, Alaumy,Shaikh, Minhaj,Singh, Shubham,Rajendran, Abinaya,Mhetre, Amol,Kamat, Siddhesh S.. "Biochemical characterization of the PHARC-associated serine hydrolase ABHD12 reveals its preference for very-long-chain lipids". . p. 16953 - 16963. Retrieved 2018/11/21.