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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

(±)11-HDoHE

Cayman Chemical Item Number 33450

11-hydroxy Docosahexaenoic Acid (CAS 87018-59-5)

(±)11-HDoHE (CAS 87018-59-5)

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Description

(±)11-HDoHE 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)-HDoHE by human platelets and canine retina.6,7,8,5 In addition to 11(S)-HDoHE, 14(S)-HDoHE is also produced by platelets.6,8,5 11(S)-HDoHE 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-HDoHE is a potential marker of oxidative stress in brain and retina where DHA is an abundant polyunsaturated fatty acid.

1 VanRollins, M., and Murphy, R.C. Autooxidation of docosahexaenoic acid: Analysis of ten isomers of hydroxydocosahexaenoate. J Lipid Res 25 507-517 (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 214 165-170 (1993).

3 VanRollins, M., Baker, R.C., Sprecher, H., et al. Oxidation of docosahexaenoic acid by rat liver microsomes. J Biol Chem 259 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 B 652 123-136 (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 40 473-490 (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. J Biol Chem 258 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 125 741-747 (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. Inhibitory effects of n-6 and n-3 hydroxy fatty acids on thromboxane (U46619)-induced smooth muscle contraction. J Pharmacol Exp Ther 270 1105-1109 (1994).

Synonyms
  • 11-hydroxy Docosahexaenoic Acid
Formal Name (±)11-​hydroxy-​4Z,​7Z,​9E,​13Z,​16Z,​19Z-​docosahexaenoic acid
CAS Number 87018-59-5
Molecular Formula C22H32O3
Formula Weight 344.5
Formulation A solution in ethanol
Purity ≥98%
λmax 237 nm
ε 24
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CC/C=C\C/C=C\C/C=C\CC(O)​\C=C\C=C\C/C=C\CCC(=O)​O

Background Reading

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

VanRollins, M., Baker, R.C., Sprecher, H., et al. Oxidation of docosahexaenoic acid by rat liver microsomes. J Biol Chem 259 5776-5783 (1984).

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

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).

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 125 741-747 (1984).

Hatmi, M., Lussiana, J.P., Junien, J.L., et al. Interference of eicosapentaenoic and docosahexaenoic acids with arachidonate-and U46619-induced platelet activation and desensitization. Biochem Pharmacol 37 481-489 (1988).

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

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 214 165-170 (1993).

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 B 652 123-136 (1994).

Sprecher, H., and Careaga, M.M. Metabolism of (n-6) and (n-3) polyunsaturated fatty acids by human platelets. Prostaglandins Leukot Med 23 129-134 (1986).

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).

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. J Biol Chem 258 9339-9343 (1983).

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(±)11-HDoHE is available in the following screening library:

Size Price Quantity Subtotal
25 µg $40.00 $0.00
50 µg $76.00 $0.00
100 µg $144.00 $0.00
250 µg $320.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

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Pricing updated 2012-02-08. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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