An inhibitor of 5-LO
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Isomer(s)
70750Caffeic Acid phenylethyl ester
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2,5-Dihydroxycinnamic Acid phenethyl ester

Item No. 29736

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E)-3-(2,5-dihydroxyphenyl)-2-propenoic acid, 2-phenylethyl ester
CAS Number
179691-97-5
Molecular Formula
C17H16O4
Formula Weight
284.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/ml
λmax
251, 280, 362 nm
SMILES
O=C(OCCC1=CC=CC=C1)/C=C/C2=CC(O)=CC=C2O
InChi Code
InChI=1S/C17H16O4/c18-15-7-8-16(19)14(12-15)6-9-17(20)21-11-10-13-4-2-1-3-5-13/h1-9,12,18-19H,10-11H2/b9-6+
InChi Key
OQKRMXDGEFRBAJ-RMKNXTFCSA-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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    1 mg

    $49

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    5 mg

    $190

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    10 mg

    $329

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    25 mg

    $762

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    Product Description

    2,5-Dihydroxycinnamic acid phenethyl ester is an inhibitor of 5-lipoxygenase (5-LO) with an IC50 value of 0.33 µM for inhibition of 5-LO product synthesis in polymorphonuclear leukocytes (PMNLs) stimulated with the sarcoendoplasmic reticulum calcium ATPase (SERCA) inhibitor thapsigargin (Item No. 10522).1 It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals (IC50 = 16.41 µM) in a cell-free assay. 2,5-Dihydroxycinnamic acid phenethyl ester selectively decreases viability of RCC4 and 786-O cells lacking the Von Hippel-Lindau (VHL) tumor suppressor gene (IC50s = 8 and 34.8 µM, respectively) over cells homozygously expressing VHL (IC50s = 99.6 and >100 µM, respectively). However, it also decreases viability of RCC10 VHL-/- and RCC10 VHL+/+ cells (IC50s = 5.04 and 0.96 µM, respectively). It increases the levels of pro-caspase-3a, LC3B-I, and LC3B-II in RCC4 VHL-/- cells in a concentration-dependent manner.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Selka, A., Doiron, J.A., Lyons, P.A., et al. Discovery of a novel 2,5-dihydroxycinnamic acid-based 5-lipoxygenase inhibitor that induces apoptosis and may impair autophagic flux in RCC4 renal cancer cells. Eur. J. Med. Chem. 179, 347-357 (2019).