Docosahexaenoic Acid

Base Information

• Chemical Name: Docosahexaenoic Acid
• CAS No.: 6217-54-5
• Deprecated CAS: 25377-50-8,1024594-51-1,231610-51-8,1008399-82-3,1005411-64-2,664303-42-8,952411-45-9
• Molecular Formula: C22H32O2
• Molecular Weight: 328.495
• Hs Code.: 29161900
• UNII: ZAD9OKH9JC
• DSSTox Substance ID: DTXSID5040465
• Nikkaji Number: J381.483A
• Wikipedia: Docosahexaenoic_acid
• Wikidata: Q423345
• NCI Thesaurus Code: C68346
• RXCUI: 1006469
• Pharos Ligand ID: S6AGCD6F6XGU
• Metabolomics Workbench ID: 610
• ChEMBL ID: CHEMBL367149
• Mol file: 6217-54-5.mol

Synonyms:Acid, Docosahexaenoic;Acids, Docosahexaenoic;Acids, Docosahexenoic;Docosahexaenoate;Docosahexaenoic Acid;Docosahexaenoic Acid (All-Z Isomer);Docosahexaenoic Acid Dimer (All-Z Isomer);Docosahexaenoic Acid, 3,6,9,12,15,18-Isomer;Docosahexaenoic Acid, 4,7,10,13,16,19-(All-Z-Isomer);Docosahexaenoic Acid, 4,7,10,13,16,19-(All-Z-Isomer), Cerium Salt;Docosahexaenoic Acid, 4,7,10,13,16,19-(All-Z-Isomer), Cesium Salt;Docosahexaenoic Acid, 4,7,10,13,16,19-(All-Z-Isomer), Potassium Salt;Docosahexaenoic Acid, 4,7,10,13,16,19-(Z,Z,Z,Z,Z,E-Isomer);Docosahexaenoic Acid, 4,7,10,13,16,19-Isomer;Docosahexaenoic Acid, 4,7,10,13,16,19-Isomer, Sodium Salt;Docosahexaenoic Acid, Sodium Salt;Docosahexaenoic Acids;Docosahexenoic Acids

Chemical Property of Docosahexaenoic Acid

Chemical Property:

• Appearance/Colour: achromaticity clarity liquid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: -44 °C
• Refractive Index: 1.521
• Boiling Point: 446.7 °C at 760 mmHg
• PKA: 4.58±0.10(Predicted)
• Flash Point: 343.4 °C
• PSA: 37.30000
• Density: 0.943 g/cm³
• LogP: 6.54890
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Heated, Son
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 14
• Exact Mass: 328.240230259
• Heavy Atom Count: 24
• Complexity: 462

Purity/Quality:

99% ^*data from raw suppliers

DocosahexaenoicAcid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids
• Canonical SMILES: CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)O
• Isomeric SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O
• Recent ClinicalTrials: Randomized Trial of DHA for Retinitis Pigmentosa Patients Receiving Vitamin A
• Recent EU Clinical Trials: Imaging the functional and molecular impact of poly-unsaturated fatty acids on dopamine-dependent cognitive functions: a combined [11C]-(+)-PHNO PET/MRI study at different stages of cognitive impairment
• Description: Docosa Hexaenoic acid (DHA) is an omega-3 fatty acid that is a primary structural component of the human brain, cerebral cortex, skin, sperm, testicles and retina. It can be synthesized from alphalinolenic acid or obtained directly from maternal milk or fish oil. DHA's structure is a carboxylic acid(~oic acid) with a 22-carbon chain (docosa- is Greek for 22) and six (Greek "hexa") cis double bonds (-en~); the first double bond is located at the third carbon from the omega end. Its trivial name is cervonic acid, its systematic name is all-cis-docosa-4,7,10,13,16,19-hexa-enoic acid, and its shorthand name is 22:6(n-3) in the nomenclature of fatty acids. Docosahexaenoic acid (DHA) is a long-chain ω-3 polyunsaturated fatty acid (PUFA) found in fish and algal oils. It comprises approximately 40% of total brain PUFAs and is abundant in grey matter and retinal membranes. DHA typically represents 0.52-7.5% of human total plasma fatty acids. It is produced from α-linolenic acid (ALA; Item Nos. 90210 | 21910) via a series of desaturase- and elongase-catalyzed reactions, resulting in a docosapentaenoic acid (DPA; ) intermediate, which is elongated, desaturated, and β-oxidized to produce DHA. DHA can be liberated from cellular membranes by phospholipase A2 (PLA2) and converted to numerous oxylipins, including specialized pro-resolving mediators (SPMs), which are produced by lipoxygenases and include D-series protectins and resolvins, as well as maresins, that regulate host defense and the resolution of inflammation. DHA has roles in several physiological and pathological processes, including neural development, cardiovascular diseases, obesity, and inflammation. DHA MaxSpec? standard is a quantitative grade standard of DHA that has been prepared specifically for mass spectrometry and related applications where quantitative reproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independently prepared calibration standard. The verified concentration is provided on the certificate of analysis. This DHA MaxSpec? standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis. Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product. Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.
• Uses: Docosahexaenoic acid is found in fish oils in nature. It is also commercially manufactured from microalgae; Crypthecodinium cohnii and Schizochytrium.

Technology Process of Docosahexaenoic Acid

There total 32 articles about Docosahexaenoic 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: 98.0%

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate (81926-94-5,84494-72-4) → docosahexaenoic acid (6217-54-5)

Guidance literature:

With ethylenediaminetetraacetic acid; edetate disodium; In ethanol; water; at 60 - 65 ℃; for 2h;

DOI:10.1016/0040-4020(94)00983-2

Reference yield: 94.0%

docosahexaenoic acid ethyl ester (84494-72-4) → docosahexaenoic acid (6217-54-5)

Guidance literature:

With lithium hydroxide monohydrate; In ethanol; water; at 60 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.08.009

Reference yield: 92.0%

all-cis-4,7,10,13,16,19-docosahexaenoic acid methyl ester (2566-90-7,875288-77-0) → docosahexaenoic acid (6217-54-5)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water;

DOI:10.1021/jo00125a065

upstream raw materials:

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate

all-cis-4,7,10,13,16,19-docosahexaenoic acid methyl ester

(Z)-3-Hexen-1-ol

1-bromo-3-hexene

Downstream raw materials:

butanoic acid ethyl ester

triglyceride of docosahexaenoic acid

(4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoic acid 2,3-dihydroxy-propyl ester

(17S)-HDHA

Refernces

• 1、 Liu, Shaojun,Zhu, Yamin,Liu, Ning,Fan, Daming,Wang, Mingfu,Zhao, Yueliang. "Antioxidative Properties and Chemical Changes of Quercetin in Fish Oil: Quercetin Reacts with Free Fatty Acids to Form Its Ester Derivatives". . p. 1057 - 1067. Retrieved 2021/02/01.
• 2、 Vu, Chi B.,Bridges, Robert J.,Pena-Rasgado, Cecilia,Lacerda, Antonio E.,Bordwell, Curtis,Sewell, Abby,Nichols, Andrew J.,Chandran, Sachin,Lonkar, Pallavi,Picarella, Dominic,Ting, Amal,Wensley, Allison,Yeager, Maisy,Liu, Feng. "Fatty Acid Cysteamine Conjugates as Novel and Potent Autophagy Activators That Enhance the Correction of Misfolded F508del-Cystic Fibrosis Transmembrane Conductance Regulator (CFTR)". . p. 458 - 473. Retrieved 2017/04/26.