(2s)-2,3-Dihydroxypropyl (9z)-Octadec-9-Enoate

Base Information

• Chemical Name: (2s)-2,3-Dihydroxypropyl (9z)-Octadec-9-Enoate
• CAS No.: 129784-87-8
• Molecular Formula: C₂₁H₄₀O₄
• Molecular Weight: 356.546
• Nikkaji Number: J264.959D
• Wikidata: Q27145531
• Mol file: 129784-87-8.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 (2s)-2,3-Dihydroxypropyl (9z)-Octadec-9-Enoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 26 - 28 °C
• Refractive Index: 1.479
• Boiling Point: 483.298°C at 760 mmHg
• Flash Point: 155.429°C
• PSA: 66.76000
• Density: 0.97g/cm³
• LogP: 4.92030
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• 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:

98%Min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)OCC(CO)O
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](CO)O
• Uses: A new fatty ester from Rhazya stricta roots (Apocynanaceae).

Technology Process of (2s)-2,3-Dihydroxypropyl (9z)-Octadec-9-Enoate

There total 45 articles about (2s)-2,3-Dihydroxypropyl (9z)-Octadec-9-Enoate 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:

silicic acid tetrakis-(2-hydroxy-3-oleoyloxy-propylester)

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

1,3-diolein

2-Oleoylglycerol

Refernces

• 1、 -. "High-selectivity synthesis method of long-chain fatty acid monoglyceride". Paragraph 0047; 0050. . Retrieved 2019/02/27.
• 2、 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.