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Docosatetraenoic acid: Difference between revisions

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Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (
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{{Chembox
{{Chembox
| Verifiedfields = changed
⚫
| verifiedrevid = 371527947
| Watchedfields = changed
⚫
| verifiedrevid = 428833652
| Name = Adrenic acid
| Name = Adrenic acid
| ImageFile = adrenic acid.png
| ImageFile = adrenic acid.png
| ImageSize = 200px
| ImageSize = 200px
| IUPACName = 7''Z'',10''Z'',13''Z'',16''Z''-docosatetraenoic acid
| PIN = (7''Z'',10''Z'',13''Z'',16''Z'')-Docosa-7,10,13,16-tetraenoic acid
| OtherNames =
| OtherNames =
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 28874-58-0
| CASNo = 28874-58-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 64F675W6EN
| PubChem = 5497181
| PubChem = 5497181
| SMILES = OC(CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O
| 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
|Section2={{Chembox Properties
| Formula = C<sub>22</sub>H<sub>36</sub>O<sub>2</sub>
| Formula = C<sub>22</sub>H<sub>36</sub>O<sub>2</sub>
| MolarMass = 332.5 g/mol
| MolarMass = 332.5 g/mol
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| BoilingPt =
| BoilingPt =
| Solubility = }}
| Solubility = }}
| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| Autoignition = }}
| AutoignitionPt = }}
}}
}}


'''Docosatetraenoic acid''' designates any straight chain 22:4 [[fatty acid]]. (''See'' [[essential fatty acid#nomenclature| essential fatty acid]] for nomenclature.)
'''Docosatetraenoic acid''' designates any straight chain 22:4 [[fatty acid]]. (''See'' [[Essential fatty acid#Nomenclature and terminology|Essential fatty acid]] for nomenclature.)


One isomer is of particular interest:
One isomer is of particular interest:
* all-''cis''-7,10,13,16-docosatetraenoic acid is an [[omega-6_fatty acid|&omega;-6 fatty acid]] with the [[trivial name]] '''adrenic acid'''. 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>
* all-''cis''-7,10,13,16-docosatetraenoic acid is an [[omega-6 fatty acid|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-[[Epoxyeicosatrienoic acid|EET]]s).<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}}</ref> In addition to being [[endothelium-derived hyperpolarizing factor]]s, 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==
==See also==
*[[Polyunsaturated fatty acid]]s
*[[Polyunsaturated fat]]
*{{slink|Docosanoid|DTA-derived docosanoids}}


==References==
==References==
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==Further reading==
==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).
*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).
*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:Fatty acids]]
[[Category:Alkenoic acids]]
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