4-[2-[(E)-octadec-9-enoyl]oxy-3-[(Z)-octadec-9-enoyl]oxypropoxy]-4-oxobutanoic acid

Base Information

• Chemical Name: 4-[2-[(E)-octadec-9-enoyl]oxy-3-[(Z)-octadec-9-enoyl]oxypropoxy]-4-oxobutanoic acid
• CAS No.: 129445-40-5
• Molecular Formula: C43H76 O8
• Molecular Weight: 721.072
• Mol file: 129445-40-5.mol

Synonyms:1,2-dioleoyl-3-succinylglycerol;1,2-dioleoyl-3-succinylglycerol, R-(Z,Z)-isomer;1,2-DOSG

Chemical Property of 4-[2-[(E)-octadec-9-enoyl]oxy-3-[(Z)-octadec-9-enoyl]oxypropoxy]-4-oxobutanoic acid

Chemical Property:

• Vapor Pressure: 5.18E-24mmHg at 25°C
• Boiling Point: 740.8°Cat760mmHg
• Flash Point: 202.6°C
• PSA: 116.20000
• Density: 0.986g/cm³
• LogP: 11.92440
• XLogP3: 14.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 41
• Exact Mass: 720.55401938
• Heavy Atom Count: 51
• Complexity: 896

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)OCC(COC(=O)CCC(=O)O)OC(=O)CCCCCCCC=CCCCCCCCC
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OCC(COC(=O)CCC(=O)O)OC(=O)CCCCCCC/C=C/CCCCCCCC

Technology Process of 4-[2-[(E)-octadec-9-enoyl]oxy-3-[(Z)-octadec-9-enoyl]oxypropoxy]-4-oxobutanoic acid

There total 3 articles about 4-[2-[(E)-octadec-9-enoyl]oxy-3-[(Z)-octadec-9-enoyl]oxypropoxy]-4-oxobutanoic acid 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: 84.0%

succinic acid anhydride (108-30-5) + 1,2-dioleoylglycerol (2442-61-7,3738-74-7,22202-42-2,24529-88-2,26540-69-2,33735-55-6,38738-56-6,98719-67-6) → 2,3-dioleoyl glycerol hemisuccinate (129445-40-5)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 14h; Inert atmosphere; Cooling with ice;

Reference yield:

1-(tert-butyl)dimethylsilyl-2,3-dioleoyl glycerol → 2,3-dioleoyl glycerol hemisuccinate (129445-40-5)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine hydrogenfluoride; pyridine / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere; Cooling with ice

2: dmap / dichloromethane / 14 h / 20 °C / Inert atmosphere; Cooling with ice

With pyridine; dmap; pyridine hydrogenfluoride; In tetrahydrofuran; dichloromethane;

Reference yield:

cis-Octadecenoic acid (112-80-1,2027-47-6) → 2,3-dioleoyl glycerol hemisuccinate (129445-40-5)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 14 h / 20 °C / Inert atmosphere; Cooling with ice

2: pyridine hydrogenfluoride; pyridine / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere; Cooling with ice

3: dmap / dichloromethane / 14 h / 20 °C / Inert atmosphere; Cooling with ice

With pyridine; dmap; pyridine hydrogenfluoride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

upstream raw materials:

succinic acid anhydride

1,2-dioleoylglycerol

cis-Octadecenoic acid

Refernces