Docosapentaenoic acid

Base Information

• Chemical Name: Docosapentaenoic acid
• CAS No.: 24880-45-3
• Molecular Formula: C₂₂H₃₄O₂
• Molecular Weight: 330.511
• UNII: NS3OZT14QT
• DSSTox Substance ID: DTXSID6074758
• Nikkaji Number: J490.555E
• Wikidata: Q3278345
• NCI Thesaurus Code: C68334
• Metabolomics Workbench ID: 3059
• ChEMBL ID: CHEMBL496634
• Mol file: 24880-45-3.mol

Synonyms:(all-Z)-7, 10, 13, 16, 19-docosapentaenoic acid;4,7,10,13,16-Docosapentaenoic acid;7,10,13,16,19-docosapentaenoic acid;7,10,13,16,19-docosapentaenoic acid, (7Z,10Z,13Z,16Z,19Z)-;7,10,13,16,19-docosapentaenoic acid, (all-Z)-isomer;7,10,13,16,19-docosapentaenoic acid, (Z,Z,Z,Z,E)-isomer;7,10,13,16,19-docosapentaenoic acid, lithium salt;7,10,13,16,19-docosapentaenoic acid, lithium salt, (all-Z)-isomer;cis-7,10,13,16,19-docosapentaenoic acid;clupanodonic acid;docosa-4,7,10,13,16-pentaenoic acid;docosa-4,7,10,13,16-pentaenoic acid 5-(14)C-labeled cpd, (all-Z)-isomer;docosa-4,7,10,13,16-pentaenoic acid, (all-Z)-isomer;docosapentaenoic acid;docosapentaenoic acid (C22:5 N3);docosapentaenoic acid (C22:5 N6);docosapentaenoic acid, (all Z)-isomer;osbond acid

Chemical Property of Docosapentaenoic acid

Chemical Property:

• Vapor Pressure: 4.69E-09mmHg at 25°C
• Refractive Index: 1.509
• Boiling Point: 442.2 °C at 760 mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 338.9 °C
• PSA: 37.30000
• Density: 0.932 g/cm³
• LogP: 6.77290
• Storage Temp.: −20°C
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 330.255880323
• Heavy Atom Count: 24
• Complexity: 425

Purity/Quality:

99% ^*data from raw suppliers

all-cis-7,10,13,16,19-Docosapentaenoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids
• Canonical SMILES: CCC=CCC=CCC=CCC=CCC=CCCCCCC(=O)O
• Isomeric SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O
• Uses: A fatty acid use to inhibit platelet aggregation CIS-7,10,13,16,19-DOCOSA-PENTAENOIC ACID is an ω-3 fatty acid found in fish oils. It is a minor constituent of the total serum unsaturated fatty acids in humans, ranging from 0.1 to 1%, and increases on dietary supplementation. all-cis-7,10,13,16,19-Docosapentaenoic Acid, also known as DPA, is a fatty acid derived from fish oils that potently inhibits platelet aggregation. DPA has been reported to block the cyclooxygenase pathway and stimulate the lipoxygenase pathway, which results in effective platelet aggregation inhibition. Peripheral blood mononuclear cell research demonstrates that DPA diminishes cyclooxygenase-2 levels intracellularly and inhibits pro-inflammatory prostaglandin E2 production.

Technology Process of Docosapentaenoic acid

There total 17 articles about Docosapentaenoic 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: 99.0%

methyl (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate (108698-02-8) → docosa-7Z,10Z,13Z,16Z,19Z-pentaenoic acid (2234-74-4,124020-08-2,24880-45-3)

Guidance literature:

With water; potassium hydroxide; In methanol; at 50 ℃; for 5h;

Reference yield: 80.0%

(7Z,10Z,13Z,16Z,19Z)-ethyl docosa-7,10,13,16,19-pentaenoate (119818-40-5) + (R)-3-amino-1,2-propanediol (66211-46-9,98923-21-8) → docosa-7Z,10Z,13Z,16Z,19Z-pentaenoic acid (2234-74-4,124020-08-2,24880-45-3) + C25H41NO3

Guidance literature:

With Novozym 435 lipase on resin; In acetone; at 35 ℃; for 8h; Green chemistry; Enzymatic reaction;

DOI:10.1016/j.bmcl.2014.10.084

Reference yield: 70.0%

(S)-3-Amino-1,2-propanediol (61278-21-5,98923-21-8) + (7Z,10Z,13Z,16Z,19Z)-ethyl docosa-7,10,13,16,19-pentaenoate (119818-40-5) → docosa-7Z,10Z,13Z,16Z,19Z-pentaenoic acid (2234-74-4,124020-08-2,24880-45-3) + C25H41NO3

Guidance literature:

With Novozym 435 lipase on resin; In acetone; at 35 ℃; for 8h; Green chemistry; Enzymatic reaction;

DOI:10.1016/j.bmcl.2014.10.084

upstream raw materials:

methyl (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate

2-((6Z,9Z,12Z,15Z,18Z)-Henicosa-6,9,12,15,18-pentaenyl)-4,4-dimethyl-4,5-dihydro-oxazole

(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester

(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaen-1-ol

Downstream raw materials:

docosapentaenoyl chloride

C₂₈H₃₉NO₂

C₂₈H₄₀N₂O

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