An autoxidation product of DHA and potential marker of oxidative stress
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(±)7-HDHA

Item No. 33300

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)7-hydroxy-4Z,8E,10Z,13Z,16Z,19Z-docosahexaenoic acid
CAS Number
90780-55-5
Synonyms
  • 7-hydroxy Docosahexaenoic Acid
  • (±)7-HDoHE
Molecular Formula
C22H32O3
Formula Weight
344.5
Purity
≥98%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
0.1 M Na2CO3: 2 mg/mlDMF: MiscibleDMSO: MiscibleEthanol: MisciblePBS (pH 7.2): 0.8 mg/ml
λmax
237 nm
SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C=C/C(O)C/C=C\CCC(=O)O
InChi Code
InChI=1S/C22H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-21(23)19-16-14-17-20-22(24)25/h3-4,6-7,9-10,12-16,18,21,23H,2,5,8,11,17,19-20H2,1H3,(H,24,25)/b4-3-,7-6-,10-9-,13-12-,16-14-,18-15+
InChi Key
OZXAIGIRPOOJTI-XJAVJPOHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $85

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    50 µg

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    100 µg

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    250 µg

    $673

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    Product Description

    (±)7-HDHA is an autoxidation product of docosahexaenoic acid (DHA) in vitro.1,2 It is also produced from incubations of DHA in rat liver, brain, and intestinal microsomes.3,4,5 Enzymatic transformation of DHA by RBL-1 cells and human neutrophils also produces 7-HDHA.6,7 However, the enzymatic product is most likely the S-isomer. (±)7-HDHA is a potential marker of oxidative stress in brain and retina where DHA is an abundant polyunsaturated fatty acid.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. VanRollins, M., and Murphy, R.C. Autooxidation of docosahexaenoic acid: Analysis of ten isomers of hydroxydocosahexaenoate. J. Lipid Res. 25(5), 507-517 (1984).

    2. Reynaud, D., Thickitt, C.P., and Pace-Asciak, C.R. Facile preparation and structural determination of monohydroxy derivatives of docosahexaenoic acid (HDoHE) by α-tocopherol-directed autoxidation. Anal. Biochem. 214(1), 165-170 (1993).

    3. VanRollins, M., Baker, R.C., Sprecher, H., et al. Oxidation of docosahexaenoic acid by rat liver microsomes. The Journal of Biological Chemisty 259(9), 5776-5783 (1984).

    4. Yamane, M., Abe, A., and Yamane, S. High-performance liquid chromatography-thermospray mass spectrometry of epoxy polyunsaturated fatty acids and epoxyhydroxy polyunsaturated fatty acids from an incubation mixture of rat tissue homogenate. J. Chromatogr. 652(2), 123-136 (1994).

    5. Kim, H.Y., Karanian, J.W., Shingu, T., et al. Sterochemical analysis of hydroxylated docosahexaenoates produced by human platelets and rat brain homogenate. Prostaglandins 40(5), 473-490 (1990).

    6. Corey, E.J., Shih, C., and Cashman, J.R. Docosahexaenoic acid is a strong inhibitor of prostaglandin but not leukotriene biosynthesis. Proc. Natl. Acad. Sci. USA 80, 3581-3584 (1983).

    7. Fischer, S., Schacky, C.V., Siess, W., et al. Uptake, release and metabolism of docosahexaenoic acid (DHA, C22:6ω3) in human platelets and neutrophils. Biochem. Biophys. Res. Commun. 120, 907-918 (1984).

    Product Citations

    Wu, Z., Xiao, H., Rao, D., et al. Analytical strategy for oxylipin annotation by combining chemical derivatization-based retention index algorithm and feature tandem mass spectrometric fragmentation as a biomarker discovery tool. Anal. Chem. 95(43), 15933-15942 (2023).

    Dalli, J., Colas, R.A., Walker, M.E., et al. Lipid Mediator Metabolomics via LC-MS/MS Profiling and Analysis. Clinical Metabolomics 59-72 (2018).

    Aoyagi, R., Ikeda, K., Isobe, Y., et al. Comprehensive analyses of oxidized phospholipids using a measured MS/MS spectra library. J. Lipid. Res. 58(11), 2229-2237 (2017).

    Morgan, A.H., Hammond, V.J., Morgan, L., et al. Quantitative assays for esterified oxylipins generated by immune cells. Nat. Protoc. 5(12), 1919-1931 (2010).