An oxylipin
Related Products
Isomer(s)
33550(±)14-HDHA
Labeled Version(s)
900276414(S)-HDHA-d5
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14(S)-HDHA

Item No. 15253

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
14S-hydroxy-4Z,7Z,10Z,12E,16Z,19Z-docosahexaenoic acid
CAS Number
119433-37-3
Synonyms
  • FA 22:6;O
  • 14(S)-HDHE
  • 14(S)-hydroxy-4(Z),7(Z),10(Z),12(E),16(Z),19(Z)-DHE
  • 14(S)-hydroxy-cis-4,7,10,16,19-trans-10-Docosahexaenoic Acid
  • 14(S)-Hydroxydocosahexaenoic Acid
Molecular Formula
C22H32O3
Formula Weight
344.5
Purity
≥98%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
0.1 M Na2CO3: 2 mg/mlDMF: MiscibleDMSO: MiscibleEthanol: MisciblePBS (pH 7.2): 0.5 mg/ml
λmax
236 nm
SMILES
CC/C=C\C/C=C\C[C@H](O)/C=C/C=C\C/C=C\C/C=C\CCC(O)=O
InChi Code
InChI=1S/C22H32O3/c1-2-3-4-5-12-15-18-21(23)19-16-13-10-8-6-7-9-11-14-17-20-22(24)25/h3-4,6-7,10-16,19,21,23H,2,5,8-9,17-18,20H2,1H3,(H,24,25)/b4-3-,7-6-,13-10-,14-11-,15-12-,19-16+/t21-/m0/s1
InChi Key
ZNEBXONKCYFJAF-OUKOMXQNSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    25 µg

    $90

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    50 µg

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    100 µg

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    Product Description

    14(S)-HDHA is an oxylipin formed by reduction of 14(S)-HpDHA, a 12-lipoxygenase-derived metabolite of DHA (Item Nos. 90310 | 17932).1 It increases PKA activity in isolated human platelets at 10 µM.2 14(S)-HDHA (5 and 10 µM) inhibits collagen-induced aggregation and convulxin-induced integrin αIIbβ3 activation and α-granule secretion in isolated human platelets. It also delays thrombus formation and reduces thrombus growth in mice at 15 mg/kg. 14(S)-HDHA has been found in mouse peritoneal exudates in a model of zymosan-induced peritonitis.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Serhan, C.N., Yang, R., Martinod, K., et al. Maresins: Novel macrophage mediators with potent antiinflammatory and proresolving actions. J. Exp. Med. 206(1), 15-23 (2009).

    2. Yamaguchi, A., Stanger, L., Freedman, C.J., et al. DHA 12-LOX-derived oxylipins regulate platelet activation and thrombus formation through a PKA-dependent signaling pathway. J. Thromb. Haemost. 19(3), 839-851 (2021).

    Product Citations

    Wu, Z., Xiao, H., Rao, D., et al. Analytical strategy for oxylipin annotation by combining chemical derivatization-based retention index algorithm and feature tandem mass spectrometric fragmentation as a biomarker discovery tool. Anal. Chem. 95(43), 15933-15942 (2023).

    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).