Docosatetraenoic acid

Adrenic acid
Names
	Preferred IUPAC name (7Z,10Z,13Z,16Z)-Docosa-7,10,13,16-tetraenoic acid
Identifiers
CAS Number	28874-58-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	4593749 ;
PubChem CID	5497181;
UNII	64F675W6EN ;
CompTox Dashboard (EPA)	DTXSID80912354 ;
	InChI InChI=1S/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- Key: TWSWSIQAPQLDBP-DOFZRALJSA-N ; 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- Key: TWSWSIQAPQLDBP-DOFZRALJBY;
	SMILES OC(CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O;
Properties
Chemical formula	C22H36O2
Molar mass	332.5 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Docosatetraenoic acid designates any straight chain 22:4 fatty acid. (See Essential fatty acid for nomenclature.)

One isomer is of particular interest:

all-cis-7,10,13,16-docosatetraenoic acid is an ω-6 fatty acid with the common name adrenic acid (AdA). This is a naturally occurring polyunsaturated fatty acid formed through a 2-carbon chain elongation of arachidonic acid. It is one of the most abundant fatty acids in the early human brain.^[1] This unsaturated fatty acid is also metabolized by cells to biologically active products viz., dihomoprostaglandins,^[2] and epoxydocosatrienoic acids (EDTs, also known as dihomo-EETs).^[3] ^[4] ^[5] In addition to being endothelium-derived hyperpolarizing factors, EDTs have demonstrated anti-endoplasmic reticulum stress and anti-nociceptive activities. They are hydrolyzed by the soluble epoxide hydrolase (sEH) to dihydroxydocosatrienoic acids (DHDTs) and hence might play a role in the efficacy of sEH inhibitors.

References

^ Martinez M (1992). "Tissue levels of polyunsaturated fatty acids during early human development". J Pediatr. 120 (4 Pt 2): S129–38. doi:10.1016/S0022-3476(05)81247-8. PMID 1532827.
^ Campbell WB, Falck JR, Okita JR, Johnson AR, Callahan KS (1985). "Synthesis of dihomoprostaglandins from adrenic acid (7,10,13,16-docosatetraenoic acid) by human endothelial cells". Biochim. Biophys. Acta. 837 (1): 67–76. doi:10.1016/0005-2760(85)90086-4. PMID 3931686.
^ Kopf PG, Zhang DX, Gauthier KM, Nithipatikom K, Yi XY, Falck JR, Campbell WB (2010). "Adrenic acid metabolites as endogenous endothelium-derived and zona glomerulosa-derived hyperpolarizing factors". Hypertension. 55 (2): 547–54. doi:10.1161/HYPERTENSIONAHA.109.144147. PMC 2819927. PMID 20038752.
^ Yi XY, Gauthier KM, Cui L, Nithipatikom K, Falck JR, Campbell WB (May 2007). "Metabolism of adrenic acid to vasodilatory 1alpha,1beta-dihomo-epoxyeicosatrienoic acids by bovine coronary arteries". Am J Physiol Heart Circ Physiol. 292 (5): H2265–74. doi:10.1152/ajpheart.00947.2006. PMID 17209008.
^ Singh N, Barnych B, Wagner KM, Wan D, Morisseau C, Hammock BD (March 2021). "Adrenic Acid-Derived Epoxy Fatty Acids Are Naturally Occurring Lipids and Their Methyl Ester Prodrug Reduces Endoplasmic Reticulum Stress and Inflammatory Pain". ACS Omega. 6 (10): 7165–7174. doi:10.1021/acsomega.1c00241. PMC 7970556. PMID 33748630.