A monoterpene lactone with diverse biological activities
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Loliolide

Item No. 34196

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(6S,7aR)-5,6,7,7a-tetrahydro-6-hydroxy-4,4,7a-trimethyl-2(4H)-benzofuranone
CAS Number
5989-02-6
Synonyms
  • (–)-Loliolide
  • NSC 289632
Molecular Formula
C11H16O3
Formula Weight
196.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
C[C@]12C(C(C)(C[C@@H](C1)O)C)=CC(O2)=O
InChi Code
InChI=1S/C11H16O3/c1-10(2)5-7(12)6-11(3)8(10)4-9(13)14-11/h4,7,12H,5-6H2,1-3H3/t7-,11+/m0/s1
InChi Key
XEVQXKKKAVVSMW-WRWORJQWSA-N
Origin
Plant/Eucommia ulmoides leaves
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $229

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    1 mg

    $435

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    Product Description

    Loliolide is a monoterpene lactone that has been found in P. urinaria and has diverse biological activities.1,2,3,4 It scavenges DPPH (Item No. 14805) and peroxide radicals in cell-free assays when used at concentrations ranging from 62.5 to 250 µM and reduces peroxide-induced apoptosis in Vero cells.1 Loliolide (10 µg/ml) inhibits LPS-induced proliferation of isolated mouse T and B cells.2 It reduces hepatitis C virus (HCV) infectivity in Huh7.5 cells (EC50 = 2.48 µM) and inhibits HCV binding to Huh7.5 cells when used at concentrations of 10 and 50 µM.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yang, X., Kang, M.-C., Lee, K.-W., et al. Antioxidant activity and cell protective effect of loliolide isolated from Sargassum ringgoldianum subsp. coreanum. Algae 26(2), 201-208 (2011).

    2. Okada, N., Shirata, K., Niwano, M., et al. Immunosuppressive activity of a monoterpene from Eucommia ulmoides. Phytochemistry 37(1), 281-282 (1994).

    3. Chung, C.-Y., Liu, C.-H., Burnouf, T., et al. Activity-based and fraction-guided analysis of Phyllanthus urinaria identifies loliolide as a potent inhibitor of hepatitis C virus entry. Antiviral Res. 130, 58-68 (2016).

    4. Okunade, A.L., and Wiemer, D.F. (–)-Loliolide, an ant-repellent compound from Xanthoxyllum setulosum. J. Nat. Prod. 48(3), 472-473 (1985).