A phthalide with diverse biological activities
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(Z)-Ligustilide

Item No. 26908

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3Z-butylidene-4,5-dihydro-1(3H)-isobenzofuranone
CAS Number
81944-09-4
Synonyms
  • cis-Ligustilide
  • Ligustilide A
Molecular Formula
C12H14O2
Formula Weight
190.2
Purity
≥95%
Formulation (Request formulation change)
A neat oil
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 1 mg/mlEthanol: Miscible
λmax
285, 322 nm
SMILES
O=C1O/C(C2=C1C=CCC2)=C\CCC
InChi Code
InChI=1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h5,7-8H,2-4,6H2,1H3/b11-8-
InChi Key
IQVQXVFMNOFTMU-FLIBITNWSA-N
Origin
Plant/Angelica sinensis
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

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    25 mg

    $169

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    50 mg

    $319

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    100 mg

    $602

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    Cayman Chemical
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    Product Description

    (Z)-Ligustilide is a phthalide that has been found in A. graveolens and T. montana roots and has diverse biological activities.1,2,3,4 It inhibits autophagy and restores Nurr77 expression and sensitivity to tamoxifen (Item No. 13258) in tamoxifen-resistant MCF-7 cells.2 (Z)-Ligustilide (8-32 mg/kg) increases cerebral expression of Nrf2 and HO-1 and reduces infarct volume and neuronal loss in a rat model of cerebral ischemia and reperfusion injury.5 It decreases mechanical and thermal hyperalgesia in a rat model of inflammatory pain induced by complete Freund's adjuvant (CFA).3 (Z)-Ligustilide restores gait coordination, reduces spinal cord inducible nitric oxide synthase (iNOS) expression, and inhibits production of prostaglandin E2 (PGE2; Item No. 14010), TNF-α, and IL-1β in a rat model of spinal cord injury.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gijbels, M.J.M., Fischer, F.C., Scheffer, J.J.C., et al. Phthalides in roots of Anethum graveolens and Todaroa montana. Scientia Pharmaceutica 51(4), 414-417 (1983).

    2. Qi, H., Jiang, Z., Wang, C., et al. Sensitization of tamoxifen-resistant breast cancer cells by Z-ligustilide through inhibiting autophagy and accumulating DNA damages. Oncotarget 8(17), 29300-29317 (2017).

    3. Wang, Y.-R., Xu, H., Tao, M., et al. Ligustilide relieves complete Freund’s adjuvant-induced mechanical hyperalgesia through inhibiting the activation of spinal c-Jun N-terminal kinase/c-Jun pathway in rats. Pharmacogn. Mag. 13(52), 634-638 (2017).

    4. Xiao, W., Yu, A., Liu, D., et al. Ligustilide treatment promotes functional recovery in a rat model of spinal cord injury via preventing ROS production. Int. J. Clin. Exp. Pathol. 8(10), 12005-12013 (2015).

    5. Peng, B., Zhao, P., Lu, Y.-P., et al. Z-ligustilide activates the Nrf2/HO-1 pathway and protects against cerebral ischemia-reperfusion injury in vivo and in vitro. Brain Res. 1520, 168-177 (2013).