See personalized New Product recommendations! Get personalized New Product recommendations! Register or Login for personalized New Product recommendations!

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

(±)17-HDoHE

Cayman Chemical Item Number 33650

17-hydroxy Docosahexaenoic Acid (CAS 90780-52-2)

(±)17-HDoHE (CAS 90780-52-2)

See more

Description

(±)17-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 17(S)-HDoHE could be produced by enzymatic oxidation of DHA using soybean lipoxygenase (LO) and is the putative product of mammalian 15-LOs.5 17(S)-HDoHE was shown to be an inhibitor of U-46619-induced rabbit and rat aortic smooth muscle contraction with IC50 values of 4.9 and 7.2 µM, respectively.6 (±)17-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 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
  • 17-hydroxy Docosahexaenoic Acid
Formal Name (±)17-​hydroxy-​4Z,​7Z,​10Z,​13Z,​15E,​19Z-​docosahexaenoic acid
CAS Number 90780-52-2
Molecular Formula C22H32O3
Formula Weight 344.5
Formulation A solution in ethanol
Purity ≥98%
λmax 236 nm
ε 10
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CC/C=C\CC(O)​\C=C\C=C\C/C=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).

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).

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).

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).

Show all 6 Hide all but first 3

(±)17-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.

Related Products

(±)10-HDoHE
(±)11-HDoHE
(±)11-HEPE
(±)11-HETE
(±)12-HEPE Exclusive
(±)12-HETE
(±)13-HDoHE
(±)13-HODE
(±)14-HDoHE
(±)15-HEPE
(±)15-HETE
(±)16-HDoHE
17(R)-HDoHE Exclusive
17(S)-HpDoHE
(±)20-HDoHE
(±)4-HDoHE
(±)5-HEPE
(±)5-HETE
(±)7-HDoHE
(±)8-HDoHE
(±)8-HEPE
(±)8-HETE
(±)9-HEPE
(±)9-HETE
(±)9-HODE
Docosahexaenoic Acid
Show all 26 Hide all but first 3

Downloads

Batch-specific Information

Login to access batch-specific information

Cayman Chemical is a manufacturer, supplier and vendor of biochemical reagents, assay kits, antibodies, and proteins.

Other Resources
Management Team Company Profile Company History ChemAssistant Tools FAQs Cayman Europe Cayman Pharma CaBRI Cayman Gear Press Releases Illustrations and Charts Key Research Area Posters Article Library Analysis Tools Conference Schedule Order Terms Browser Recommendation Privacy Statement Site Map

Cayman Chemical Company · 1180 East Ellsworth Road · Ann Arbor, Michigan 48108 · USA

Toll Free: (800) 364-9897 (USA and Canada Only) · Fax: (734) 971-3640

Copyright 2012 Cayman Chemical Company

Lost password?