7-Hydroxydocosa-4,8,10,13,16,19-hexaenoic acid

Base Information

• Chemical Name: 7-Hydroxydocosa-4,8,10,13,16,19-hexaenoic acid
• CAS No.: 90780-55-5
• Molecular Formula: C₂₂H₃₂O₃
• Molecular Weight: 344.494
• DSSTox Substance ID: DTXSID00694004
• Mol file: 90780-55-5.mol

Synonyms:7-hydroxydocosa-4,8,10,13,16,19-hexaenoic acid;(+/-)7-HDHA;90780-55-5;(+/-)7-HDoHE;DTXSID00694004

Chemical Property of 7-Hydroxydocosa-4,8,10,13,16,19-hexaenoic acid

Chemical Property:

• PSA: 57.53000
• LogP: 5.51970
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 344.23514488
• Heavy Atom Count: 25
• Complexity: 493

Purity/Quality:

99% ^*data from raw suppliers

(±)?-?7-?Hydroxy-?4Z,?8E,?10Z,?13Z,?16Z,?19Z-?docosahexaenoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC=CCC=CCC=CC=CC(CC=CCCC(=O)O)O
• Uses: (±)?-?7-?Hydroxy-?4Z,?8E,?10Z,?13Z,?16Z,?19Z-?docosahexaenoic Acid is an auto-oxidation product of DHA (D494500), an omega-3 fatty acid found in marine fish oils and in many phospholipids. Major structural component of excitable membranes of the retina and brain; synthesized in the liver from α-linolenic acid. Nutritional supplement.

Technology Process of 7-Hydroxydocosa-4,8,10,13,16,19-hexaenoic acid

There total 16 articles about 7-Hydroxydocosa-4,8,10,13,16,19-hexaenoic 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: 80.0%

C24H36O3 → (±)-(4Z,8E,10Z,13Z,16Z,19Z)-7-hydroxydocosa-4,8,10,13,16,19-hexaenoic acid (90780-55-5)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1021/acs.joc.0c01770

Reference yield:

2,5-octadiynyl bromide (1558-79-8) → (±)-(4Z,8E,10Z,13Z,16Z,19Z)-7-hydroxydocosa-4,8,10,13,16,19-hexaenoic acid (90780-55-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 0 - 20 °C

2.1: nickel(II) acetate tetrahydrate; hydrogen; sodium tetrahydroborate; ethylenediamine / ethanol / 20 °C

3.1: potassium carbonate / tetrahydrofuran; methanol / 3 h / 20 °C

4.1: diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 0.5 h

4.2: 20 °C

5.1: Zn(Cu/Ag) / methanol; water; 1,4-dioxane / 6 h / 45 °C

5.2: 48 h / 45 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

7.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 20 °C

With sodium tetrahydroborate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium hydroxide monohydrate; tetrabutyl ammonium fluoride; hydrogen; nickel(II) acetate tetrahydrate; potassium carbonate; ethylenediamine; diisopropylamine; sodium iodide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/acs.joc.0c01770

Reference yield:

trimethyl(trideca-1,4,7,10-tetrayn-1-yl)silane → (±)-(4Z,8E,10Z,13Z,16Z,19Z)-7-hydroxydocosa-4,8,10,13,16,19-hexaenoic acid (90780-55-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: nickel(II) acetate tetrahydrate; hydrogen; sodium tetrahydroborate; ethylenediamine / ethanol / 20 °C

2.1: potassium carbonate / tetrahydrofuran; methanol / 3 h / 20 °C

3.1: diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 0.5 h

3.2: 20 °C

4.1: Zn(Cu/Ag) / methanol; water; 1,4-dioxane / 6 h / 45 °C

4.2: 48 h / 45 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

6.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 20 °C

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium hydroxide monohydrate; tetrabutyl ammonium fluoride; hydrogen; nickel(II) acetate tetrahydrate; potassium carbonate; ethylenediamine; diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water;

DOI:10.1021/acs.joc.0c01770

upstream raw materials:

2,5-octadiynyl bromide

1-(1,3-dioxolan-2-yl)but-3-yn-2-ol

pent-2-yn-1-ol

Refernces