The predominant lipoxygenase product of mammalian platelets
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12(S)-HETE

Item No. 34570

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
12S-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid
CAS Number
54397-83-0
Synonyms
  • 12(S)-Hydroxyeicosatetraenoic Acid
Molecular Formula
C20H32O3
Formula Weight
320.5
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: 0.8 mg/ml
λmax
237 nm
SMILES
CCCCC/C=C\C[C@H](O)/C=C/C=C\C/C=C\CCCC(O)=O
InChi Code
InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1
InChi Key
ZNHVWPKMFKADKW-LQWMCKPYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $164

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    50 µg

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    100 µg

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    Product Description

    12(S)-HETE is the predominant lipoxygenase product of mammalian platelets.1 It enhances tumor cell adhesion to endothelial cells, fibronectin, and the subendothelial matrix at 0.1 µM.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hamberg, M., and Samuelsson, B. Prostaglandin endoperoxides. Novel transformations of arachidonic acid in human platelets. Proc. Natl. Acad. Sci. USA 71(9), 3400-3404 (1974).

    2. Grossi, I.M., Fitzgerald, L.A., Umbarger, L.A., et al. Bidirectional control of membrane expression and/or activation of the tumor cell IRGpIIb/IIIa receptor and tumor cell adhesion by lipoxygenase products of arachidonic acid and linoleic acid. Cancer Res. 49(4), 1029-1037 (1989).

    3. 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(5), 413-429 (1992).

    Product Citations

    Misheva, M., Kotzamanis, K., Davies, L.C., et al. Oxylipin metabolism is controlled by mitochondrial β-oxidation during bacterial inflammation. Nat. Commun. 13(1), 139 (2022).

    Banthiya, S., Kalms, J., Yoga, E.G., et al. Structural and functional basis of phospholipid oxygenase activity of bacterial lipoxygenase from Pseudomonas aeruginosa. Biochim. Biophys. Acta 1861, 1681-1692 (2016).

    Honn, K.V., Guo, Y., Cai, Y., et al. 12-HETER1/GPR31, a high-affinity 12(S)-hydroxyeicosatetraenoic acid receptor, is significantly up-regulated in prostate cancer and plays a critical role in prostate cancer progression. The FASEB Journal 30(6), 2360-2369 (2016).

    Sasaki, A., Fukuda, H., Shiida, N., et al. Determination of ω-6 and ω-3 PUFA metabolites in human urine samples using UPLC/MS/MS. Anal. Bioanal. Chem. 407(6), 1625-1639 (2015).

    Morgan, A.H., Hammond, V.J., Morgan, L., et al. Quantitative assays for esterified oxylipins generated by immune cells. Nat. Protoc. 5(12), 1919-1931 (2010).

    Chavis, C., Fraissinet, L., Chanez, P., et al. A method for the measurement of plasma hydroxyeicosatetraenoic acid levels. Anal. Biochem. 271(1), 105-108 (1999).

    Rao, C.V., Desai, D., Rivenson, A., et al. Chemoprevention of colon carcinogenesis by phenylethyl-3-methylcaffeate. Cancer Res. 55(11), 2310-2315 (1995).