A lactone form of (±)5(6)-DiHET
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(±)5(6)-DiHET lactone

Item No. 51212

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
tetrahydro-6-[(3Z,6Z,9Z)-1-hydroxy-3,6,9-pentadecatrien-1-yl]-2H-pyran-2-one
CAS Number
213126-92-2
Synonyms
  • (±)5,6-DiHETrE lactone
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)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS pH 7.2: 1 mg/ml
SMILES
O=C(O1)CCC[C@@H]1[C@H](O)C/C=C\C/C=C\C/C=C\CCCCC
InChi Code
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18(21)19-16-14-17-20(22)23-19/h6-7,9-10,12-13,18-19,21H,2-5,8,11,14-17H2,1H3/b7-6-,10-9-,13-12-/t18-,19-/m1/s1
InChi Key
FVXUUVSFGPLNBJ-GMKBZGQBSA-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

    $102

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    50 µg

    $192

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    100 µg

    $357

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    250 µg

    $791

    Add
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    Product Description

    5,6-DiHET lactone is a lactonized form of 5,6-EET and 5,6-DiHET. In solution, 5(6)-EET degrades into 5(6)-DiHET and 5(6)-δ-lactone, which can be converted to 5(6)-DiHET and quantified by GC-MS.1 5,6-DiHET potently induces vasodilation of isolated canine coronary arterioles, with 41 and 100% inhibition occurring at 0.01 and 100 pM, respectively.2 It also induces vasodilation in isolated human microvessels and increases intracellular calcium levels in a dose-dependent manner, an effect that can be blocked by the nitric oxide scavenger L-NAME (Item No. 80210).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rashid, M., Manivet, P., Nishio, H., et al. Identification of the binding sites and selectivity of sarpogrelate, a novel 5-HT2 antagonist, to human 5-HT2A, 5-HT2B and 5-HT2C receptor subtypes by molecular modeling. Life Sci. 73(2), 193-207 (2003).

    2. Oltman, C.L., Weintraub, N.L., VanRollins, M., et al. Epoxyeicosatrienoic acids and dihydroxyeicosatrienoic acids are potent vasodilators in the canine coronary microcirculation. Circ. Res. 83(9), 932-939 (1998).

    3. Levi-Rosenzvig, R., Beyer, A.M., Hockenberry, J., et al. 5,6-δ-DHTL, a stable metabolite of arachidonic acid, is a potential EDHF that mediates microvascular dilation. Free Rad. Biol. Med. 103, 87-94 (2017).

    Product Citations

    Levi-Rosenzvig, R., Beyer, A.M., Hockenberry, J., et al. 5,6-δ-DHTL, a stable metabolite of arachidonic acid, is a potential EDHF that mediates microvascular dilation. Free Rad. Biol. Med. 103, 87-94 (2017).