An aspirin-triggered epimer of resolvin D3
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Isomer(s)
13834Resolvin D3
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17(R)-Resolvin D3

Item No. 9002880

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4S,5Z,7E,9E,11R,13Z,15E,17R,19Z)-4,11,17-trihydroxy-5,7,9,13,15,19-docosahexaenoic acid
CAS Number
1427475-53-3
Synonyms
  • Aspirin-triggered Resolvin D3
  • 17-epi-Resolvin D3
  • AT-RvD3
  • 17(R)-RvD3
Molecular Formula
C22H32O5
Formula Weight
376.5
Purity
≥90%
Formulation (Request formulation change)
A 50 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: unstableEthanol: 50 mg/mlPBS (pH 7.2): 0.5 mg/ml
λmax
240, 272, 283 nm
SMILES
O[C@H](C/C=C\CC)/C=C/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCC(O)=O
InChi Code
InChI=1S/C22H32O5/c1-2-3-7-12-19(23)14-10-6-11-15-20(24)13-8-4-5-9-16-21(25)17-18-22(26)27/h3-11,13-14,16,19-21,23-25H,2,12,15,17-18H2,1H3,(H,26,27)/b5-4+,7-3-,11-6-,13-8+,14-10+,16-9-/t19-,20+,21-/m1/s1
InChi Key
QBTJOLCUKWLTIC-AXRBAIMGSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    10 µg

    $169

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    25 µg

    $400

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    50 µg

    $758

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    100 µg

    $1,347

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    Product Description

    17(R)-Resolvin D3 (17(R)-RvD3) is an aspirin-triggered epimer of resolvin D3 (Item No. 13834).1 It is produced from docosahexaenoic acid (DHA; Item No. 90310) by COX-2 in the presence of aspirin via a 17(R)-hydroperoxy DHA (17(R)-HDHA; Item No. 10005099) intermediate and has been found in mouse inflammatory exudates.1,2 17(R)-RvD3 reduces transmigration of isolated human polymorphonuclear cells (PMNs) and induces efferocytosis of apoptotic PMNs by macrophages.2 17(R)-RvD3 (10 ng/animal) reduces transmigration of neutrophils into the peritoneal cavity, as well as decreases the levels of IL-6 and increases the levels of IL-10 in inflammatory exudate in a mouse model of zymosan-induced peritonitis. It activates GPR32 in a β-arrestin reporter assay and increases phagocytosis to a greater degree in CHO cells overexpressing GPR32 compared to mock-transfected cells. 17(R)-RvD3 increases phagocytosis of etoposide-generated tumor cell debris by monocyte-derived macrophages in H460 human lung carcinoma cells in a concentration-dependent manner.3 It also inhibits tumor growth in a mouse model of Lewis lung carcinoma when administered at a dose of 0.6 µg/kg per day.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Winkler, J.W., Uddin, J., Serhan, C.N., et al. Stereocontrolled total synthesis of the potent anti-inflammatory and pro-resolving lipid mediator resolvin D3 and its aspirin-triggered 17R-epimer. Org. Lett. 15(7), 1424-1427 (2013).

    2. Dalli, J., Winkler, J.W., Colas, R.A., et al. Resolvin D3 and aspirin-triggered resolvin D3 are potent immunoresolvents. Chem. Biol. 20(2), 188-201 (2013).

    3. Gilligan, M.M., Gartng, A., Sulcier, M.L., et al. Aspirin-triggered proresolving mediators stimulate resolution in cancer. Proc. Natl. Acad. Sci. USA 116(13), 6292-6297 (2019).