{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 428833652 | Name = Adrenic acid | ImageFile = adrenic acid.png | ImageSize = 200px | PIN = (7''Z'',10''Z'',13''Z'',16''Z'')-Docosa-7,10,13,16-tetraenoic acid | OtherNames = |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 28874-58-0 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 64F675W6EN | PubChem = 5497181 | SMILES = OC(CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 4593749 | 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- | InChIKey = TWSWSIQAPQLDBP-DOFZRALJBY | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 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- | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = TWSWSIQAPQLDBP-DOFZRALJSA-N }} |Section2={{Chembox Properties | Formula = C<sub>22</sub>H<sub>36</sub>O<sub>2</sub> | MolarMass = 332.5 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''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.<ref name=Martinez >{{cite journal |author=Martinez M |title=Tissue levels of polyunsaturated fatty acids during early human development |journal=J Pediatr |volume=120 |issue=4 Pt 2 |pages=S129–38 |year=1992 |pmid=1532827 |doi=10.1016/S0022-3476(05)81247-8}}</ref> This unsaturated fatty acid is also metabolized by cells to biologically active products viz., dihomoprostaglandins,<ref name=Campbell>{{cite journal |vauthors=Campbell WB, Falck JR, Okita JR, Johnson AR, Callahan KS|author2-link=John R. Falck |title=Synthesis of dihomoprostaglandins from adrenic acid (7,10,13,16-docosatetraenoic acid) by human endothelial cells |journal=Biochim. Biophys. Acta |volume=837 |issue=1 |pages=67–76 |year=1985 |pmid=3931686 |doi=10.1016/0005-2760(85)90086-4}}</ref> and epoxydocosatrienoic acids (EDTs, also known as dihomo-EETs).<ref name="pmid20038752">{{cite journal | vauthors = Kopf PG, Zhang DX, Gauthier KM, Nithipatikom K, Yi XY, Falck JR, Campbell WB | title = Adrenic acid metabolites as endogenous endothelium-derived and zona glomerulosa-derived hyperpolarizing factors | journal = Hypertension | volume = 55 | issue = 2 | pages = 547–54 | year = 2010 | pmid = 20038752 | pmc = 2819927 | doi = 10.1161/HYPERTENSIONAHA.109.144147 }}</ref><ref name=Yi>{{cite journal |journal= Am J Physiol Heart Circ Physiol |date =May 2007| volume=292|issue=5|pages=H2265–74 | title=Metabolism of adrenic acid to vasodilatory 1alpha,1beta-dihomo-epoxyeicosatrienoic acids by bovine coronary arteries. |vauthors=Yi XY, Gauthier KM, Cui L, Nithipatikom K, Falck JR, Campbell WB |pmid=17209008 | doi=10.1152/ajpheart.00947.2006}}<!--|accessdate=2007-10-30 --></ref><ref name=Singh>{{cite journal |journal= ACS Omega |date =March 2021| volume=6|issue=10|pages=7165–7174 | title=Adrenic Acid-Derived Epoxy Fatty Acids Are Naturally Occurring Lipids and Their Methyl Ester Prodrug Reduces Endoplasmic Reticulum Stress and Inflammatory Pain. |vauthors=Singh N, Barnych B, Wagner KM, Wan D, Morisseau C, Hammock BD | doi=10.1021/acsomega.1c00241|pmc=7970556|doi-access=free|pmid =33748630}}</ref> 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.
==See also== *Polyunsaturated fat *{{slink|Docosanoid|DTA-derived docosanoids}}
==References== {{reflist}}
==Further reading== *Ferretti, A., Flanagan, V.P. Mass spectrometric evidence for the conversion of exogenous adrenate to dihomo-prostaglandins by seminal vesicle cyclo-oxygenase. A comparative study of two animal species. J Chromatogr 383 241-250 (1986). *Sprecher, H., VanRollins, M., Sun, F., et al. Dihomo-prostaglandins and -thromboxane. A prostaglandin family from adrenic acid that may be preferentially synthesized in the kidney. J Biol Chem 257 3912-3918 (1982).
{{fatty acids}}
Category:Fatty acids Category:Alkenoic acids