A neolignan with antioxidative and antiparasitic activities
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Dieugenol

Item No. 27557

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,3'-dimethoxy-5,5'-di-2-propen-1-yl-[1,1'-biphenyl]-2,2'-diol
CAS Number
4433-08-3
Synonyms
  • Bis-Eugenol
  • Dehydrodieugenol
Molecular Formula
C20H22O4
Formula Weight
326.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: solubleDMSO: solubleMethanol: soluble
SMILES
OC1=C(C2=C(O)C(OC)=CC(CC=C)=C2)C=C(CC=C)C=C1OC
InChi Code
InChI=1S/C20H22O4/c1-5-7-13-9-15(19(21)17(11-13)23-3)16-10-14(8-6-2)12-18(24-4)20(16)22/h5-6,9-12,21-22H,1-2,7-8H2,3-4H3
InChi Key
KETPSFSOGFKJJY-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $63

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    5 mg

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    10 mg

    $481

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    Cayman Chemical
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    Product Description

    Dieugenol is a neolignan that has been found in N. leucantha and has antioxidative and antiprotozoal activities.1,2 It inhibits the formation of thiobarbituric acid reactive substances (TBARS) and scavenges superoxide anions, but not hydroxyl radicals, in cell-free assays.1 It has anti-trypanosomal activity against T. cruzi amastigotes and trypomastigotes (IC50s = 15.1 and 11.5 µM, respectively) but is cytotoxic to NCTC L-929 fibroblasts with a 50% cytotoxic concentration (CC50) value of 58.2 µM.2 Dieugenol (15 µM) disrupts the integrity of the T. cruzi trypomastigote plasma membrane but does not induce the production of reactive oxygen species (ROS) in trypomastigotes or LPS-stimulated and unstimulated isolated mouse peritoneal macrophages.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ogata, M., Hoshi, M., Urano, S., et al. Antioxidant activity of eugenol and related monomeric and dimeric compounds. Chem. Pharm. Bull. (Tokyo) 48(10), 1467-1469 (2000).

    2. Grecco, S.S., Costa-Silva, T.A., Jerz, G., et al. Antitrypanosomal activity and evaluation of the mechanism of action of dehydrodieugenol isolated from Nectandra leucantha (Lauraceae) and its methylated derivative against Trypanosoma cruzi. Phytomedicine 24, 62-67 (2017).