7,10,13,16-Docosatetraenoic acid

Base Information

• Chemical Name: 7,10,13,16-Docosatetraenoic acid
• CAS No.: 28874-58-0
• Molecular Formula: C₂₂H₃₆O₂
• Molecular Weight: 332.527
• UNII: 8BAV9DA2XJ
• DSSTox Substance ID: DTXSID80912354
• Nikkaji Number: J13.758H,J323.447I
• Mol file: 28874-58-0.mol

Synonyms:7,10,13,16-docosatetraenoic acid;adrenic acid;adrenic acid, (Z)-isomer

Chemical Property of 7,10,13,16-Docosatetraenoic acid

Chemical Property:

• Vapor Pressure: 5.94E-09mmHg at 25°C
• Boiling Point: 439.5°Cat760mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 336.2°C
• PSA: 37.30000
• Density: 0.921g/cm³
• LogP: 6.99690
• Storage Temp.: −20°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 7.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 16
• Exact Mass: 332.271530387
• Heavy Atom Count: 24
• Complexity: 389

Purity/Quality:

NLT 98% ^*data from raw suppliers

cis-7,10,13,16-Docosatetraenoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CCC=CCCCCCC(=O)O
• Isomeric SMILES: CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCCCCC(=O)O
• Description: Adrenic acid is a naturally occurring polyunsaturated fatty acid (PUFA) formed through a 2-carbon chain elongation of arachidonic acid. It is present in the adrenal glands, brain, testis, and kidney. Although there is trace metabolism of adrenic acid in the forebrain, the renal medulla is the only tissue which readily metabolizes the acid through cyclooxygenase activity. The primary metabolite of adrenic acid in the rabbit kidney is 1a,1b-dihomo prostaglandin E2.
• Uses: Adrenic acid is considered a sort of storage form of arachidnoic acid because it can be retro-converted into arachidonic acid by enzymes. Arachidonic acid is relatively abundant especially in the phospholipids that are found in cellular membranes, and it is precursor for many hormone-like signaling molecules, e.g. prostaglandins and leukotrienes. It shall be liberated from the phospholipids by phospholipase enzymes before it can be converted into these signaling molecules. Omnivorous humans also consume small amounts of arachidonic acid with the diet, since arachidonic acid is found in small amounts in all animal products. Arachidonic acid is not found in higher plants. Arachidonic acid serves many important functions in the body, e.g. as a structural element in membrane phospholipids, and as precursor for signalling. cis-7,10,13,16-Docosatetraenoic Acid has been identified as a protein kinase inhibitor, affecting serotonin levels in studies.

Technology Process of 7,10,13,16-Docosatetraenoic acid

There total 6 articles about 7,10,13,16-Docosatetraenoic 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:

((5Z,8Z,11Z,14Z)-2-Icosa-5,8,11,14-tetraenyl)-malonic acid → adrenic acid (2091-25-0,28874-58-0)

Guidance literature:

With hydrogenchloride; In diethylene glycol dimethyl ether; at 120 ℃; for 1h; Yield given;

Reference yield:

methyl arachidonate (2566-89-4) → adrenic acid (2091-25-0,28874-58-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 65 percent / LiAlH₄ / diethyl ether / 3 h / Ambient temperature

2: 82 percent / PPh₃*Br₂ / acetonitrile

3: 1.) Na / 1.)diglyme 2.) diglyme 140 deg C, 2h

4: 40percent aq NaOH / H₂O; ethanol / 4 h / Ambient temperature

5: 1.5 M HCl / bis-(2-methoxy-ethyl) ether / 1 h / 120 °C

With hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; sodium; triphenylphosphine dibromide 1:1 addition complex; In diethyl ether; ethanol; diethylene glycol dimethyl ether; water; acetonitrile;

Reference yield:

arachidonyl alcohol (13487-46-2) → adrenic acid (2091-25-0,28874-58-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / PPh₃*Br₂ / acetonitrile

2: 1.) Na / 1.)diglyme 2.) diglyme 140 deg C, 2h

3: 40percent aq NaOH / H₂O; ethanol / 4 h / Ambient temperature

4: 1.5 M HCl / bis-(2-methoxy-ethyl) ether / 1 h / 120 °C

With hydrogenchloride; sodium hydroxide; sodium; triphenylphosphine dibromide 1:1 addition complex; In ethanol; diethylene glycol dimethyl ether; water; acetonitrile;

upstream raw materials:

methyl arachidonate

arachidonyl alcohol

(5Z,8Z,11Z,14Z)-1-bromoeicosa-5,8,11,14-tetraene

((5Z,8Z,11Z,14Z)-2-Icosa-5,8,11,14-tetraenyl)-malonic acid diethyl ester

Downstream raw materials:

docosatetraenoyl ethanolamide

Refernces