An autoxidation product of DHA and potential marker of oxidative stress
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(±)11-HDHA

Item No. 33450

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)11-hydroxy-4Z,7Z,9E,13Z,16Z,19Z-docosahexaenoic acid
CAS Number
87018-59-5
Synonyms
  • 11-hydroxy Docosahexaenoic Acid
  • (±)11-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\CC(O)\C=C\C=C\C/C=C\CCC(=O)O
InChi Code
InChI=1S/C22H32O3/c1-2-3-4-5-6-7-9-12-15-18-21(23)19-16-13-10-8-11-14-17-20-22(24)25/h3-4,6-7,10-16,19,21,23H,2,5,8-9,17-18,20H2,1H3,(H,24,25)/b4-3-,7-6-,13-10-,14-11-,15-12-,19-16+
InChi Key
LTERDCBCHFKFRI-BGKMTWLOSA-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

    $301

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    250 µg

    $663

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    Product Description

    (±)11-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 DHA is metabolized to 11(S)-HDHA by human platelets and canine retina.6,7,8,5 In addition to 11(S)-HDHA, 14(S)-HDHA is also produced by platelets.6,8,5 11(S)-HDHA was shown to be an inhibitor of U-46619-induced human platelet aggregation and rabbit and rat aortic smooth muscle contraction with IC50 values of about 50, 4.7, and 7.5 µM, respectively.8,9 (±)11-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. Aveldaño, M.I., and Sprecher, H. Synthesis of hydroxy fatty acids from 4,7,10,13,16,19-[1-14C] docosahexaenoic acid by human platelets. The Journal of Biological Chemisty 258(15), 9339-9343 (1983).

    7. Bazan, N.G., Birkle, D.L., and Reddy, T.S. Docosahexaenoic acid (22:6, n-3) is metabolized to lipoxygenase reaction products in the retina. Biochem. Biophys. Res. Commun. 125(2), 741-747 (1984).

    8. Lagarde, M., Croset, M., Guichardant, M., et al. Role of lipoxygenase products in platelet function: Relation to fatty acid modified phospholipids. Adv. Exp. Med. Biol. 192, 327-335 (1985).

    9. Karanian, J.W., Kim, H.Y., and Salem, N., Jr. Inhibitory effects of n-6 and n-3 hydroxy fatty acids on thromboxane (U46619)-induced smooth muscle contraction. J. Pharmacol. Exp. Ther. 270(3), 1105-1109 (1994).

    Product Citations

    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).