LIPID MAPS

Structure Database (LMSD)

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Common Name

(+/-)-7-HDoHE

Systematic Name

(+/-)-7-hydroxy-4Z,8E,10Z,13Z,16Z,19Z-docosahexaenoic acid

Synonyms

(+/-)7-HDHA

LM ID

LMFA04000025

Formula

C₂₂H₃₂O₃

Exact Mass

Calculate m/z

344.235146

Sum Composition

FA 22:6;O

Status

Curated

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Classification

Biological Context

(±)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.

This information has been provided by Cayman Chemical

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. 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).

3. 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).

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. 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).

6. 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).

7. 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).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010

Pubmed ID: 20671299

DOI: 10.1194/jlr.M009449

String Representations

InChiKey (Click to copy)

OZXAIGIRPOOJTI-XJAVJPOHSA-N

InChi (Click to copy)

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+

SMILES (Click to copy)

C(CC/C=C\CC(O)/C=C/C=C\C/C=C\C/C=C\C/C=C\CC)(=O)O