Lysophosphatidic acid

Base Information

• Chemical Name: Lysophosphatidic acid
• CAS No.: 22002-87-5
• Molecular Formula: C21H41 O7 P
• Molecular Weight: 436.526
• Hs Code.: 2931900090
• European Community (EC) Number: 244-710-0
• UNII: PG6M3969SG
• DSSTox Substance ID: DTXSID001015741
• Nikkaji Number: J225.507C
• Wikipedia: Lysophosphatidic_acid
• Wikidata: Q2823281
• Pharos Ligand ID: 4A8MQ931MDUN
• ChEMBL ID: CHEMBL1222042
• Mol file: 22002-87-5.mol

Synonyms:1-O-oleyllysophosphatidic acid;1-oleoyl-lyso-phosphatidic acid;1-oleoyl-lysophosphatidic acid;9-octadecenoic acid (9Z)-, 2-hydroxy-3-(phosphonooxy)propyl ester;LPA (lysophosphatidic acid);lysophosphatidic acid;monooleylphosphatidate;monooleylphosphatidic acid;monooleylphosphatidic acid, (R)-isomer;monooleylphosphatidic acid, sodium salt, (R)-isomer

Chemical Property of Lysophosphatidic acid

Chemical Property:

• Vapor Pressure: 6.04E-16mmHg at 25°C
• Boiling Point: 581.5°Cat760mmHg
• Flash Point: 305.5°C
• PSA: 123.10000
• Density: 1.103g/cm³
• LogP: 5.03730
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 21
• Exact Mass: 436.25899064
• Heavy Atom Count: 29
• Complexity: 462

Purity/Quality:

99% ^*data from raw suppliers

1-Oleoyl Lysophosphatidic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O)O)O
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OCC(COP(=O)(O)O)O
• Use Description: 2-hydroxy-3-(phosphonooxy)propyl oleate is a compound with potential applications in various fields. In the field of agriculture and horticulture, it can serve as a plant growth regulator and nutrient delivery system. Its unique chemical structure allows it to promote root development, nutrient uptake, and overall plant health. This compound can enhance crop yields and improve the efficiency of fertilizers, contributing to sustainable agriculture practices and increased food production. Additionally, in the field of cosmetic and personal care products, it may find use as an ingredient in skincare and haircare formulations due to its emollient and conditioning properties, helping to moisturize and protect the skin and hair. Its significance varies within these fields, but it consistently plays a role in promoting healthy plant growth and offering skincare benefits across diverse scientific and industrial applications.

Technology Process of Lysophosphatidic acid

There total 2 articles about Lysophosphatidic 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: 78.0%

→ 1-oleoyl-2-lyso-sn-glycero-3-phosphate (22002-87-5,65528-98-5)

Guidance literature:

Reference yield:

dioleoylphosphatidylcholine (68737-67-7) → 1-oleoyl-2-lyso-sn-glycero-3-phosphate (22002-87-5,65528-98-5)

Guidance literature:

DOI:10.1271/bbb.70044

upstream raw materials:

dioleoylphosphatidylcholine

Refernces

Efficient synthesis of 3-O-thia-cPA and preliminary analysis of its biological activity toward autotaxin

10.1016/j.bmcl.2011.05.083

The research focuses on the efficient synthesis of 3-O-thia-cPAs (4a–d), sulfur analogues of cyclic phosphatidic acid (cPA), with the key step being an intramolecular Arbuzov reaction to construct the cyclic thiophosphate moiety. The synthetic route allows for the production of 4a–d in just four steps from commercially available glycidol. Preliminary biological experiments were conducted to assess the inhibitory effect of 4a–d on autotaxin (ATX), an enzyme involved in controlling the concentration of lysophosphatidic acid (LPA), which affects cell proliferation and cancer cell metastasis. The study used various reactants including glycidol, thioacetic acid, methanol, 2,4-dinitrobenzenesulfenyl chloride, and phosphite, among others, to synthesize the target compounds. The chemical structures of the synthesized compounds were confirmed using NMR (1H NMR, 31P NMR, and HH-COSY) and mass spectrometry. The biological activity was evaluated through ATX inhibition assays, which showed that 3-O-thia-cPAs exhibited a similar inhibitory effect on ATX as the original cPA, with the potency order being 2-O-ccPA 3c > 3-O-thia-cPAs 4a–d > cPA 2a.