An active metabolite of arachidonic acid
Related Products
Enantiomer(s)
3457012(S)-HETE
Isomer(s)
34550(±)12-HETE
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12(R)-HETE

Item No. 34560

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
12R-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid
CAS Number
82337-46-0
Synonyms
  • 12(R)-Hydroxyeicosatetraenoic Acid
Molecular Formula
C20H32O3
Formula Weight
320.5
Purity
≥98%
Formulation
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
236 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-/m1/s1
InChi Key
ZNHVWPKMFKADKW-ZYBDYUKJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $156

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    50 µg

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    100 µg

    $432

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    Product Description

    12(R)-HETE is an endogenous active metabolite of the ω-6 PUFA and eicosanoid precursor arachidonic acid.1,2 It is formed from arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) by 12R-lipoxygenase (12R-LO), as well as cytochrome P450s (CYPs). 12(R)-HETE binds to the TP receptor in washed isolated human platelets (IC50 = 0.734 µM) and inhibits platelet aggregation induced by the TP receptor agonist I-BOP (Item No. 19600; IC50 = 3.6 µM).3 It also selectively binds to leukotriene B4 (LTB4) receptor 2 (BLT2) over BLT1 at 5 µM in CHO cell membranes expressing the human receptors.4 It increases the proliferation of HT-29 colon cancer cells when used at a concentration of 1 µM.5 12(R)-HETE inhibits the bovine corneal Na+/K+-ATPase in a concentration-dependent manner and decreases intraocular pressure in rabbits when administered topically at doses of 1, 10, or 50 µg/eye.6,7 Intracerebroventricular administration of 12(R)-HETE (10 µg/animal) decreases LPS-induced pyresis in rats.8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hawkins, D.J., and Brash, A.R. Eggs of the sea urchin, Strongylocentrotus purpuratus, contain a prominent (11R) and (12R) lipoxygenase activity. The Journal of Biological Chemisty 262(16), 7629-7634 (1987).

    2. Capdevila, J., Yadagiri, P., Manna, S., et al. Absolute configuration of the hydroxyeicosatetraenoic acids (HETEs) formed during catalytic oxygenation of arachidonic acid by microsomal cytochrome P-450. Biochem. Biophys. Res. Commun. 141(3), 1007-1011 (1986).

    3. Mais, D.E., Saussy, D.L., Jr., Magee, D.E., et al. Interaction of 5-HETE, 12-HETE, 15-HETE and 5,12-diHETE at the human platelet thromboxane A2/prostaglandin H2 receptor. Eicosanoids 3(2), 121-124 (1990).

    4. Yokomizo, T., Kato, K., Hagiya, H., et al. Hydroxyeicosanoids bind to and activate the low affinity leukotriene B4 receptor, BLT2. The Journal of Biological Chemisty 276(15), 12454-12459 (2001).

    5. Bortuzzo, C., Hanif, R., Kashfi, K., et al. The effect of leukotrienes B and selected HETEs on the proliferation of colon cancer cells. Biochim. Biophys. Acta 1300(3), 240-246 (1996).

    6. Schwartzman, M.L., Balazy, M., Masferrer, J., et al. 12(R)-Hydroxyeicosatetraenoic acid: A cytochrome P450-dependent arachidonate metabolite that inhibits Na+,K+-ATPase in the cornea. Proc. Natl. Acad. Sci. USA 84(22), 8125-8129 (1987).

    7. Masferrer, J.L., Dunn, M.W., and Schwartzman, M.L. 12(R)-Hydroxyeicosatetraenoic acid, an endogenous corneal arachidonate metabolite, lowers intraocular pressure in rabbits. Invest. Ophthalmol. Vis. Sci. 31(3), 535-539 (1990).

    8. Kozak, W., Kluger, M.J., Kozak, A., et al. Role of cytochrome P-450 in endogenous antipyresis. Am. J. Physiol. Regul. Integr. Comp. Physiol. 279(2), R455-R460 (2000).