A stilbene derivative with antioxidant and anticancer activities
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(E)-2-(2-Chlorostyryl)-3,5,6-trimethylpyrazine

Item No. 9003202

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[(1E)-2-(2-chlorophenyl)ethenyl]-3,5,6-trimethyl-pyrazine
CAS Number
1000672-89-8
Synonyms
  • CSTMP
Molecular Formula
C15H15ClN2
Formula Weight
258.8
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 2 mg/mlEthanol: 2 mg/ml
λmax
238, 278, 340 nm
SMILES
CC1=C(C)N=C(C)C(/C=C/C2=CC=CC=C2Cl)=N1
InChi Code
InChI=1S/C15H15ClN2/c1-10-11(2)18-15(12(3)17-10)9-8-13-6-4-5-7-14(13)16/h4-9H,1-3H3/b9-8+
InChi Key
SFDPYTYLNQFVAT-CMDGGOBGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $36

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    5 mg

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    10 mg

    $236

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    25 mg

    $502

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    Cayman Chemical
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    Product Description

    (E)-2-(2-Chlorostyryl)-3,5,6-trimethylpyrazine (CSTMP) is a stilbene derivative with antioxidant and anticancer activities.1,2,3 It stimulates proliferation of hydrogen peroxide-damaged ECV-304 cells (EC50 = 24.9 nM).1 CSTMP reduces hydrogen peroxide-induced release of lactate dehydrogenase (LDH) in and increases viability of human umbilical vein endothelial cells (HUVECs) in a concentration-dependent manner via inhibition of apoptosis.2 It reverses hydrogen peroxide-induced release of malondialdehyde (MDA) and decreases in superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px) activities as well as increases constitutive nitric oxide synthase (cNOS) activity and nitric oxide (NO) production in HUVECs. CSTMP also induces cell death of A549 non-small cell lung cancer (NSCLC) cells in an IRE1α-dependent manner through induction of IRE1α-TRAF2-ASK1 complex-mediated endoplasmic reticulum (ER) stress and mitochondrial apoptosis.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Deng, L., Guo, X., Zhai, L., et al. Ligustrazine derivatives. Part 4: Design, synthesis, and biological evaluation of novel ligustrazine-based stilbene derivatives as potential cardiovascular agents. Chem. Biol. Drug Des. 79(5), 731-739 (2012).

    2. Zhai, L., Zhang, P., Sun, R.-Y., et al. Cytoprotective effects of CSTMP, a novel stilbene derivative, against H2O2-induced oxidative stress in human endothelial cells. Pharmacol. Rep. 63(6), 1469-1480 (2011).

    3. Zhang, J., Liang, Y., Lin, Y., et al. IRE1α-TRAF2-ASK1 pathway is involved in CSTMP-induced apoptosis and ER stress in human non-small cell lung cancer A549 cells. Biomed. Pharmacother. 82, 281-289 (2016).