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

(±)7-HDoHE

Cayman Chemical Item Number 33300

7-hydroxy Docosahexaenoic Acid (CAS 90780-55-5)

(±)7-HDoHE (CAS 90780-55-5)

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Description

(±)7-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 Enzymatic transformation of DHA by RBL-1 cells and human neutrophils also produces 7-HDoHE.6,7 However, the enzymatic product is most likely the S-isomer. (±)7-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 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).

Synonyms
  • 7-hydroxy Docosahexaenoic Acid
Formal Name (±)7-​hydroxy-​4Z,​8E,​10Z,​13Z,​16Z,​19Z-​docosahexaenoic acid
CAS Number 90780-55-5
Molecular Formula C22H32O3
Formula Weight 344.5
Formulation A solution in ethanol
Purity ≥98%
λmax 237 nm
ε 28
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CC/C=C\C/C=C\C/C=C\C/C=C\C=C/C(O)​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).

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).

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).

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).

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).

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).

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(±)7-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.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-02-12. 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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