An oxidation product of DHA
Related Products
Enantiomer(s)
1000509917(R)-HDHA
Isomer(s)
33650(±)17-HDHA
Labeled Version(s)
2979717(S)-HDHA-d5
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17(S)-HDHA

Item No. 10009799

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
17(S)-hydroxy-4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoic acid
CAS Number
92693-03-3
Synonyms
  • 17(S)-hydroxy DHA
  • 17(S)-hydroxy Docosahexaenoic Acid
  • 17(S)-HDHE
  • 17(S)-HDoHE
Molecular Formula
C22H32O3
Formula Weight
344.5
Purity
≥98%
Formulation
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: MiscibleDMSO: MiscibleEthanol: MisciblePBS (pH 7.2): 0.8 mg/ml
λmax
237 nm
SMILES
CC/C=C\C[C@H](O)/C=C/C=C\C/C=C\C/C=C\C/C=C\CCC(O)=O
InChi Code
InChI=1S/C22H32O3/c1-2-3-15-18-21(23)19-16-13-11-9-7-5-4-6-8-10-12-14-17-20-22(24)25/h3,5-8,11-16,19,21,23H,2,4,9-10,17-18,20H2,1H3,(H,24,25)/b7-5-,8-6-,13-11-,14-12-,15-3-,19-16+/t21-/m0/s1
InChi Key
SWTYBBUBEPPYCX-YTQNUIGOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    25 µg

    $77

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    50 µg

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    100 µg

    $256

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    250 µg

    $600

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    Product Description

    17(S)-HDHA is a hydroxy fatty acid formed from docosahexaenoic acid (DHA; Item No. 90310) by 15-lipoxygenase (15-LO) and is a precursor to 17(S)-resolvins.1,2 17(S)-HDHA inhibits platelet 12-LO (IC50 = 0.4 μM).2 It inhibits TNF-α-induced expression of IL1B in a human glial cell line (IC50 = ~0.5 nM).1 17(S)-HDHA (100 nM) inhibits NOD-, LRR-, and pyrin domain-containing protein 3 (NLRP3) inflammasome formation induced by homocysteine in podocytes.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hong, S., Gronert, K., Devchand, P.R., et al. Novel docosatrienes and 17S-resolvins generated from docosahexaenoic acid in murine brain, human blood, and glial cells. Autacoids in anti-inflammation. The Journal of Biological Chemisty 278(17), 14677-14687 (2003).

    2. Mitchell, P.D., Hallam, C., Hemsley, P.E., et al. Inhibition of platelet 12-lipoxygenase by hydroxy-fatty acids. Biochem. Soc. Trans. 12, 839-841 (1984).

    3. Li, G., Chen, Z., Bhat, O.M., et al. NLRP3 inflammasome as a novel target for docosahexaenoic acid metabolites to abrogate glomerular injury. J. Lipid Res. 58(6), 1080-1090 (2017).

    Product Citations

    Mainka, M., George, S., Angioni, C., et al. On the biosynthesis of specialized pro-resolving mediators in human neutrophils and the influence of cell integrit. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1867(3), 159093 (2022).

    Meriwether, D., Sulaiman, D., Volpe, C., et al. Apolipoprotein A-I mimetics mitigate intestinal inflammation in COX2-dependent inflammatory bowel disease model. J. Clin. Invest. 130, 3670-3685 (2019).

    Dangi, B., Obeng, M., Nauroth, J.M., et al. Biogenic synthesis, purification, and chemical characterization of anti-inflammatory resolvins derived from docosapentaenoic acid (DPAn-6). The Journal of Biological Chemisty 284, 14744-14759 (2009).