1-HEXADECYL-2-OLEOYL-SN-GLYCERO-3-PHOSPHORYLCHOLINE

Base Information

• Chemical Name: 1-HEXADECYL-2-OLEOYL-SN-GLYCERO-3-PHOSPHORYLCHOLINE
• CAS No.: 95403-34-2
• Molecular Formula: C₄₂H₈₄NO₇P
• Molecular Weight: 746.105
• Mol file: 95403-34-2.mol

Synonyms:1-HEXADECYL-2-OLEOYL-SN-GLYCERO-3-PHOSPHORYLCHOLINE;1-O-hexadecyl-2-oleoyl-sn-glycero-3-phosphocholine;C16-18:1 PC

Chemical Property of 1-HEXADECYL-2-OLEOYL-SN-GLYCERO-3-PHOSPHORYLCHOLINE

Chemical Property:

• PSA: 103.93000
• LogP: 12.71160
• Storage Temp.: -20°C

Purity/Quality:

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: C16-18:1 PC or 1-O-hexadecyl-2-oleoyl-sn-glycero-3-phosphocholine may be used in the liposome binding assay. It may also be used as a lipid standard for quantification of glycerophosphocholine by liquid chromatography–mass spectrometry (LC–MS). C16-18:1 PC or 1-O-hexadecyl-2-oleoyl-sn-glycero-3-phosphocholine may be used: as a lipid standard for quantification of glycerophosphocholine by liquid chromatography–mass spectrometry (LC–MS), in preparation of phospholipid vesicles, as a substrate to study the substrate specificity of phospholipase B/lipase (PLB/LIP) in the presence and absence of deoxycholate (DOC).

Technology Process of 1-HEXADECYL-2-OLEOYL-SN-GLYCERO-3-PHOSPHORYLCHOLINE

There total 6 articles about 1-HEXADECYL-2-OLEOYL-SN-GLYCERO-3-PHOSPHORYLCHOLINE 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:

methanesulfonic acid hexadecyl ester (20779-14-0) → 1-hexadecyl-2-((Z)-9-octadecenoyl)-sn-glycero-3-phosphocholine (95403-34-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaH / 1.) THF, 50-55 deg C, 30 min, 2.) THF, reflux, 8 h

2: 86 percent / H₂ / 10percent Pd/C / methanol; CHCl₃ / 12 h / Ambient temperature

3: 95.5 percent / triethylamine, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂; dimethylformamide / 24 h / Ambient temperature

4: 60.9 percent / 4-(N,N-dimethylamino)pyridine, DCC / CH₂Cl₂ / 96 h / Ambient temperature

5: 66.7 percent / pyridinium p-toluenesulfonate, MeOH / CH₂Cl₂ / 0 - 5 °C

6: 1.) Et₃N / 1.) CH₂Cl₂, RT, overnight, 2.) CHCl₃, EtOH, from 70 deg C to 80 deg C

With methanol; dmap; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(97)00341-8

Reference yield:

1-hexadecyl-2,3-dibenzylglycerol (174289-76-0) → 1-hexadecyl-2-((Z)-9-octadecenoyl)-sn-glycero-3-phosphocholine (95403-34-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / H₂ / 10percent Pd/C / methanol; CHCl₃ / 12 h / Ambient temperature

2: 95.5 percent / triethylamine, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂; dimethylformamide / 24 h / Ambient temperature

3: 60.9 percent / 4-(N,N-dimethylamino)pyridine, DCC / CH₂Cl₂ / 96 h / Ambient temperature

4: 66.7 percent / pyridinium p-toluenesulfonate, MeOH / CH₂Cl₂ / 0 - 5 °C

5: 1.) Et₃N / 1.) CH₂Cl₂, RT, overnight, 2.) CHCl₃, EtOH, from 70 deg C to 80 deg C

With methanol; dmap; hydrogen; pyridinium p-toluenesulfonate; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(97)00341-8

Reference yield:

(R)-3-(hexadecyloxy)-1,2-propanediol (10550-58-0) → 1-hexadecyl-2-((Z)-9-octadecenoyl)-sn-glycero-3-phosphocholine (95403-34-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 95.5 percent / triethylamine, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂; dimethylformamide / 24 h / Ambient temperature

2: 60.9 percent / 4-(N,N-dimethylamino)pyridine, DCC / CH₂Cl₂ / 96 h / Ambient temperature

3: 66.7 percent / pyridinium p-toluenesulfonate, MeOH / CH₂Cl₂ / 0 - 5 °C

4: 1.) Et₃N / 1.) CH₂Cl₂, RT, overnight, 2.) CHCl₃, EtOH, from 70 deg C to 80 deg C

With methanol; dmap; pyridinium p-toluenesulfonate; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(97)00341-8

upstream raw materials:

2-chloroethyl phosphorodichloridate

triethylamine

1-hexadecyl-2-((Z)-9-octadecenoyl)-D-glycerol

(R)-3-(hexadecyloxy)-1,2-propanediol