17-oxo-4(Z),7(Z),10(Z),13(Z),15(E),19(Z)-Docosahexaenoic Acid

• CAT Number: R067396
• CAS Number: 1233715-28-0
• Molecular Formula: C22H30O3
• Molecular Weight: 342.5
• Purity: ≥95%
• Synonyms: EFOX;17-oxo-4(Z),7(Z),10(Z),13(Z),15(E),19(Z)-DHA;17-oxo-DHA
• Storage: -80°C
• InChI: InChI=1S/C22H30O3/c1-2-3-15-18-21(23)19-16-13-11-9-7-5-4-6-8-10-12-14-17-20-22(24)25/h3,5-8,11-16,19H,2,4,9-10,17-18,20H2,1H3,(H,24,25)/b7-5-,8-6-,13-11-,14-12-,15-3-,19-16+
• InChIKey: QCEBQMMZCFADMF-VIIQGJSXSA-N
• SMILES: CC/C=CCC(=O)/C=CC=CC/C=CC/C=CC/C=CCCC(=O)O

Docosahexaenoic acid (DHA; Item No. 90310) is an essential fatty acid and the most abundant ω-<wbr></wbr>3 fatty acid in neural tissues, especially in the retina and brain. 17-<wbr></wbr>keto-<wbr></wbr>4(Z),7(Z),10(Z),13(Z),15(E),19(Z)-<wbr></wbr>DHA is a metabolite of lipoxygenase-<wbr></wbr>mediated oxidation of DHA that is produced endogenously by aspirin-<wbr></wbr>enhanced COX-<wbr></wbr>2 activity. It has been shown to activate Nrf2-<wbr></wbr>dependent antioxidant gene expression, to act as a PPARγ agonist (EC50 = ~200 nM), and to inhibit pro-<wbr></wbr>inflammatory cytokine and nitric oxide production at biological concentration ranges (5-<wbr></wbr>25 µM).

Reference

1.Butovich, I.A. A one-step method of 10,17-dihydro(pero)xydocosahexa-4Z,7Z,11E,13Z,15E,19Z-enoic acid synthesis by soybean lipoxygenase. Journal of Lipid Research 47, 854-863 (2006).