An internal standard for the quantification of (S)-bromoenol lactone
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Unlabeled Version(s)
10006801(S)-Bromoenol lactone
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(S)-Bromoenol lactone-d7

Item No. 10535

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6E-(bromoethylene)tetrahydro-3S-(1-naphthalenyl-2,3,4,5,6,7,8-d7)-2H-pyran-2-one
Synonyms
  • (S)-BEL-d7
Molecular Formula
C16H6BrD7O2
Formula Weight
324.2
Purity
≥99% deuterated forms (d1-d7)
Formulation (Request formulation change)
A 1 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 25 mg/mlEthanol: 5 mg/mlPBS (pH 7.2): 0.05 mg/ml
λmax
280 nm
SMILES
[2H]C1=C([2H])C([2H])=C2C(C([2H])=C([2H])C([2H])=C2[C@@]3([H])C(O/C(CC3)=C/Br)=O)=C1[2H]
InChi Code
InChI=1S/C16H13BrO2/c17-10-12-8-9-15(16(18)19-12)14-7-3-5-11-4-1-2-6-13(11)14/h1-7,10,15H,8-9H2/b12-10+/t15-/m0/s1/i1D,2D,3D,4D,5D,6D,7D
InChi Key
BYUCSFWXCMTYOI-LJJQZJCESA-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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    100 µg

    $41

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    500 µg

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    1 mg

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    Product Description

    (S)-Bromoenol lactone-d7 ((S)-BEL-d7) is intended for use as an internal standard for the quantification of (S)-BEL by GC- or LC-MS. The phospholipases are an extensive family of lipid hydrolases that function in cell signaling, digestion, membrane remodeling, and as venom components.1 The calcium-independent phospholipase A2 (iPLA2) are a PLA2 subfamily closely associated with the release of arachidonic acid in response to physiologic stimuli. (S)-Bromoenol lactone ((S)-BEL) is an irreversible, chiral, mechanism-based inhibitor of iPLA2β that inhibits the vasopressin-induced release of arachidonate from cultured rat aortic smooth muscle (A10) cells with an IC50 value of 2 µM.2 (S)-BEL is more than 1,000-fold selective for iPLA2 versus cPLA2, and is 10-fold selective for iPLA2β versus iPLA2γ.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Balsinde, J., Balboa, M.A., Insel, P.A., et al. Regulation and inhibition of phospholipase A2. Annu. Rev. Pharmacol. Toxicol. 39, 175-189 (1999).

    2. Jenkins, C.M., Han, X., Mancuso, D.J., et al. Identification of calcium-independent phospholipase A2 (iPLA2) β, and not iPLA2γ, as the mediator of arginine vasopressin-induced arachidonic acid release in A-10 smooth muscle cells. The Journal of Biological Chemisty 277(36), 32807-32814 (2002).