1-Hexadecyl-glycero-3-phosphate

Base Information

• Chemical Name: 1-Hexadecyl-glycero-3-phosphate
• CAS No.: 52603-03-9
• Molecular Formula: C19H41O6P
• Molecular Weight: 396.49900
• Metabolomics Workbench ID: 21205
• Nikkaji Number: J813.421I
• Wikidata: Q27132823
• Mol file: 52603-03-9.mol

Synonyms:1-Hexadecyl Lysophosphatidic Acid;1-hexadecyl-glycero-3-phosphate;52603-03-9;PA(O-16:0/0:0);1-hexadecyl-sn-glycerol 3-phosphate;SCHEMBL7820593;CHEBI:63818;(2R)-3-(hexadecyloxy)-2-hydroxypropyl dihydrogen phosphate;XLVRFPVHQPHXAA-LJQANCHMSA-N;HMS3650F15;1-palmityl-sn-glycerol 3-phosphate;EX-A7245;1-Hexadecyl-sn-glyceryl-3-phosphate;LMGP10060005;1-Hexadecyl-glycero-3-phosphoric acid;HY-W127502;PD019586;CS-0185730;1-Hexadecyl-2-hydroxy-sn-glycero-3-phosphate;1-O-Hexadecyl-2-hydroxy-sn-glycero-3-phosphate;SR-01000946339;SR-01000946339-1;Q27132823;1,2-Propanediol, 3-(hexadecyloxy)-, 1-(dihydrogen phosphate), (2R)-

Chemical Property of 1-Hexadecyl-glycero-3-phosphate

Chemical Property:

• PSA: 106.03000
• LogP: 4.95450
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 20
• Exact Mass: 396.26407602
• Heavy Atom Count: 26
• Complexity: 334

Purity/Quality:

97% ^*data from raw suppliers

1-Hexadecyl Lysophosphatidic Acid ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCOCC(COP(=O)(O)O)O
• Isomeric SMILES: CCCCCCCCCCCCCCCCOC[C@H](COP(=O)(O)O)O

Technology Process of 1-Hexadecyl-glycero-3-phosphate

There total 4 articles about 1-Hexadecyl-glycero-3-phosphate 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: 90.0%

3-O-dibenzylphosphoryl-1-O-hexadecyl-sn-glycerol (396091-85-3) → 1-O-hexadecyl-3-O-phosphoryl-sn-glycerol (52603-03-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 2h; under 760.051 Torr;

DOI:10.1021/jo010734+

Reference yield:

1-Hexadecanol (36653-82-4,124-29-8) → 1-O-hexadecyl-3-O-phosphoryl-sn-glycerol (52603-03-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / BF₃*Et₂O / CH₂Cl₂ / 10 h

2: 90 percent / H₂ / Pd/C / ethyl acetate / 2 h / 760.05 Torr

With boron trifluoride diethyl etherate; hydrogen; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1021/jo010734+

Reference yield:

2-Chloro-4-hexadecyloxymethyl-[1,3,2]dioxaphospholane 2-oxide → 1-palmityl-sn2-hydroxide-rac-glycero-3-phosphonate (66322-35-8,52603-03-9) + Phosphoric acid mono-(1-hexadecyloxymethyl-2-trityloxy-ethyl) ester (200956-49-6)

Guidance literature:

With pyridine; water; trityl chloride; Yield given. Multistep reaction. Yields of byproduct given; 1.) RT, 3 h, 2.) RT, 24 h;

upstream raw materials:

trityl chloride

3-O-dibenzylphosphoryl-1-O-hexadecyl-sn-glycerol

1-Hexadecanol

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