Docosatetraenoic acid

Adrenic acid

Names
IUPAC name 7Z,10Z,13Z,16Z-docosatetraenoic acid
Identifiers
CAS Number	28874-58-0
3D model (Jmol)	Interactive image
ChemSpider	4593749
PubChem	5497181
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).
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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 trivial 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] dihomo-epoxyeicosatrienoic acids, ^[3] and dihomo-EETs.^[4]

See also

• Polyunsaturated fatty acids
• Docosanoid#DTA-derived docosanoids

References

1. 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.
2. 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.
3. 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.
4. 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.

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).