28874-58-0

Basic information

• Product Name: ADRENIC ACID
• Synonyms: 7Z,10Z,13Z,16Z-DOCOSATETRAENOIC ACID;ADRENIC ACID;CIS-7,10,13,16,19-DOCOSA-TETRAENOIC ACID;CIS-7,10,13,16-DOCOSA-TETRAENOIC ACID;DOCOSATETRAENOIC ACID;DOCOSA-7Z,10Z,13Z,16Z-PENTAENOIC ACID;DOCOSA-7Z,10Z,13Z,16Z-TETRAENOIC ACID;cis-7,10,13,16-Docosatetraenoic acid, C22:4n6
• CAS NO: 28874-58-0
• Molecular Formula: C22H36O2
• Molecular Weight: 332.52
• Product Categories: Omega 6 fatty acids and derivatives;Polyunsaturated;Unsaturated fatty acids and derivatives;DJ - DZUnsaturated fatty acids and derivatives;Alphabetic;D
• Mol File: 28874-58-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 439.5°Cat760mmHg
• Flash Point: 336.2°C
• Appearance: /
• Density: 0.921g/cm³
• Vapor Pressure: 5.94E-09mmHg at 25°C
• Refractive Index: 1.498
• Storage Temp.: −20°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 4.76±0.10(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: ADRENIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: ADRENIC ACID(28874-58-0)
• EPA Substance Registry System: ADRENIC ACID(28874-58-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 28874-58-0(Hazardous Substances Data)

Usage

Description

Adrenic acid, also known as cis-7,10,13,16-docosatetraenoic acid, is a naturally occurring polyunsaturated fatty acid (PUFA) formed through a 2-carbon chain elongation of arachidonic acid. It is an ω-6 fatty acid and is one of the most abundant fatty acids in the early human brain. Adrenic acid is present in the adrenal glands, brain, testis, and kidney, playing a crucial role in various physiological processes.

Uses

1. Used in the Human Body:
Adrenic acid is used as a structural element in membrane phospholipids for maintaining cellular integrity and as a precursor for hormone-like signaling molecules, such as prostaglandins and leukotrienes, which are essential for various physiological functions.
2. Used in the Renal Medulla:
Adrenic acid is used as a substrate for cyclooxygenase activity in the renal medulla, where it is metabolized to produce 1a,1b-dihomo prostaglandin E2, a primary metabolite with potential physiological roles.
3. Used in the Brain:
Adrenic acid is used as a component of the early human brain, where it contributes to the development and functioning of the central nervous system.
4. Used in Protein Kinase Inhibition Studies:
Adrenic acid is used as a protein kinase inhibitor in research studies, affecting serotonin levels and providing insights into the molecular mechanisms underlying various physiological processes.

Enzyme inhibitor

This long-chain, unsaturated fatty acid (FWfree-acid = 332.53 g/mol; CAS 28874-58-0), also known as adrenic acid and (7Z,10Z,13Z,16Z)- docosatetraenoic acid, inhibits arachidonyl-CoA synthetase, orarachidonate:CoA ligase and prostaglandin biosynthesis.

InChI:InChI=1/C22H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-,16-15-

Upstream product

• 2566-89-4 methyl arachidonate 
• 339570-70-6 ((5Z,8Z,11Z,14Z)-2-Icosa-5,8,11,14-tetraenyl)-malonic acid diethyl ester 
• 108803-63-0 (5Z,8Z,11Z,14Z)-1-bromoeicosa-5,8,11,14-tetraene 
• 13487-46-2 arachidonyl alcohol 

Downstream Products

• 150314-35-5 docosatetraenoyl ethanolamide 

Relevant articles and documents

Synthesis of C2-elongated polyunsaturated fatty acids

The synthesis by a modified malonic ester procedure of C2-elongated polyunsaturated fatty acids from their natural precursors was described. Using the suggested Scheme 1, (7Z,11Z,14Z)-7,11,14-eicosatrienoic, (8Z,11Z,14Z,17Z)-8,11,14,17-eicosatetraenoic, (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoic, (8Z,11Z,14Z,17Z)-8,11,14,17-docosatetraenoic, (7Z,10Z,13Z,16Z,19Z)-7,10,13,16,19-docosapentaenoic, and (6Z,9Z,12Z,15Z,18Z,21Z)-6,9,12,15,18,21-tetracosahexaenoic acids were synthesized. Their structures were confirmed by GC, UV, and MS data, which coincided with those of natural compounds. The target compounds were shown to be free from by-products, which could result from Z-E isomerization or migration of double bonds. The overall yields of the four-step synthesis of C2-elongated polyenoic acids were 25-30%.