| Identification | Back Directory | [Name]
Z-LIGUSTILIDE | [CAS]
81944-09-4 | [Synonyms]
Ligustilide A
cis-Ligustilide
Z-Ligustilide - in acetonitrile
(Z)-Ligustilide (Chloroform Solution)
cis-Ligustilide
DISCONTINUED. See L397900
(E)-6,7-transdihydroxyChemicalbookligustilide
LIGUSTILIDE, Z-(IN ACETONITRILE)(10.2Mg/ML)(P)
(Z)-3-butylidene-4,5-dihydroisobenzofuran-1(3H)-one
(3Z)-3-Butylidene-4,5-dihydro-1(3H)-isobenzofuranone
1(3H)-Isobenzofuranone, 3-butylidene-4,5-dihydro-, (3Z)- | [Molecular Formula]
C12H14O2 | [MDL Number]
MFCD01861511 | [MOL File]
81944-09-4.mol | [Molecular Weight]
190.24 |
| Chemical Properties | Back Directory | [Boiling point ]
168 °C | [density ]
1.10±0.1 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
-20°C, protect from light, stored under nitrogen | [solubility ]
DMF:1.0(Max Conc. mg/mL);5.26(Max Conc. mM)
DMSO:50.5(Max Conc. mg/mL);265.45(Max Conc. mM) | [form ]
Liquid | [color ]
Colorless to light yellow | [LogP]
1.710 (est) |
| Hazard Information | Back Directory | [Uses]
(Z)-Ligustilide is extracted from Ligusticum chuanxiong Hort, has antimicrobial and antifungal activity, exhibits an average antifungal score of 5.6[1]. (Z)-Ligustilide is orally active, it inhibits the expression of FATP5 and DGAT, inhibits fatty acid uptake and esterification in mice and has potential as therapeutics for nonalcoholic fatty liver disease (NAFLD) [2]. (Z)-Ligustilide is also able to reactivate ERα, has epigenetic regulation, and is used in the study of tamoxifen-resistant breast cancer[3]. | [Definition]
ChEBI: (Z)-ligustilide is a butenolide. It has a role as a metabolite. | [in vivo]
Z-ligustilide (50 mg/kg, p.o., once daily for 6 weeks) significantly reduces hepatic lipid accumulation in high-fat diet-induced fatty liver mice, inhibiting fatty acid uptake and esterification, demonstrating potential application value for non-alcoholic fatty liver disease (NAFLD)[2]. | Animal Model: |
High-fat diet (HFD)-induced fatty liver model in male C57BL/6 mice[2] | | Dosage: | 50 mg/kg | | Administration: | Oral gavage (p.o.), once daily for 6 weeks | | Result: | Significantly reduced high-fat diet (HFD)-induced hepatic fat accumulation in mice, as confirmed by hepatic TG assay, H&E staining, and Oil Red O staining, showing a marked decrease in liver lipid content.
Significantly inhibited the expression of fatty acid uptake-related genes CD36 and DGAT2, and reduced the expression of SREBP1c and its downstream target genes FAS and SCD1, thereby decreasing lipid production in the liver. |
| [IC 50]
ERα | [References]
[1] Rodrigues AMS, et al. The antifungal potential of (Z)-ligustilide and the protective effect of eugenol demonstrated by a chemometric approach. Sci Rep. 2019 Jun 19;9(1):8729. doi: 10.1038/s41598-019-45222-y DOI:10.1038/s41598-019-45222-y
[2] Lee W, et al. Z-ligustilide and n-Butylidenephthalide Isolated from the Aerial Parts of Angelica tenuissima Inhibit Lipid Accumulation In Vitro and In Vivo. Planta Med. 2019 Jul;85(9-10):719-728. DOI:10.1055/a-0901-1307
[3] Ma H, et al. Z-ligustilide restores tamoxifen sensitivity of ERa negative breast cancer cells by reversing MTA1/IFI16/HDACs complex mediated epigenetic repression of ERa. Oncotarget. 2017 Apr 25;8(17):29328-29345. DOI:10.18632/oncotarget.16440 |
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