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12(S)-HEPE

Cayman Chemical Item Number 32550

(CAS 116180-17-7)

12(S)-HEPE (CAS 116180-17-7)

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Description

12(S)-HEPE is a monohydroxy fatty acid synthesized from EPA by the action of 12-LO. Unstimulated neutrophils metabolize 12(S)-HEPE to 12(S),20-diHEPE, whereas stimulated neutrophils produce 5(S),12(S)-HEPE via the 5-lipoxygenase pathway.1 The competitive action of 12(S)-HEPE with arachidonic acid as a substrate for 5-LO in the formation of leukotrienes may provide a basis for the anti-inflammatory potential of ω-3 fatty acids.

1 von Schacky, C., Marcus, A.J., Safier, L.B., et al. Platelet-neutrophil interactions. 12S,20- and 5S,12S-dihydroxyeicosapentaenoic acids: Two novel neutrophil metabolites from platelet-derived 12S-hydroxyeicosapentaenoic acid. J Lipid Res 31 801-810 (1990).

Formal Name 12S-​hydroxy-​5Z,​8Z,​10E,​14Z,​17Z-​eicosapentaenoic acid
CAS Number 116180-17-7
Molecular Formula C20H30O3
Formula Weight 318.5
Formulation A solution in ethanol
Purity ≥98%
λmax 237 nm
ε 23
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CC/C=C\C/C=C\CC(O)​\C=C\C=C\C/C=C\CCCC(=O)​O

Background Reading

Hamberg, M., and Samuelsson, B. Prostaglandin endoperoxides. Novel transformations of arachidonic acid in human platelets. Proc Natl Acad Sci USA 71 3400-3404 (1974).

von Schacky, C., Marcus, A.J., Safier, L.B., et al. Platelet-neutrophil interactions. 12S,20- and 5S,12S-dihydroxyeicosapentaenoic acids: Two novel neutrophil metabolites from platelet-derived 12S-hydroxyeicosapentaenoic acid. J Lipid Res 31 801-810 (1990).

Honn, K.V., Nelson, K.K., Renaud, C., et al. Fatty acid modulation of tumor cell adhesion to microvessel endothelium and experimental metastasis. Prostaglandins 44 413-429 (1992).
Size Price Quantity Subtotal
25 µg $182.00 $0.00
50 µg $346.00 $0.00
100 µg $655.00 $0.00
250 µg $1,456.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

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Pricing updated 2012-05-26. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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Eicosapentaenoic Acid
HEPES Stock Solution (1 M)
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