(Z)-Ligustilide is found in Ligusticum chuanxiong Hort and has antibacterial and antifungal activity with an antifungal score of 5.6. (Z)-Ligustilide inhibits the expression of FATP5 and DGAT, inhibits the uptake and esterification of fatty acids in mice, and may be used for studying non-alcoholic fatty liver disease (NAFLD). (Z)-Ligustilide can also reactivate ERα, has epigenetic regulatory effects, and may be utilized in study/research of Tamoxifen-resistant breast cancer.

Physicochemical Properties

Molecular Formula	C12H14O2
Molecular Weight	190.24
Exact Mass	190.099
CAS #	81944-09-4
Related CAS #	(Z)-Ligustilide-d7;(E)-Ligustilide;81944-08-3
PubChem CID	5319022
Appearance	Colorless to light yellow liquid
Density	1.1±0.1 g/cm3
Boiling Point	377.9±11.0 °C at 760 mmHg
Melting Point	168～169℃
Flash Point	158.6±16.7 °C
Vapour Pressure	0.0±0.9 mmHg at 25°C
Index of Refraction	1.545
LogP	2.63
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Heavy Atom Count	14
Complexity	345
Defined Atom Stereocenter Count	0
SMILES	C(=C1/OC(=O)C2C=CCCC/1=2)/CCC
InChi Key	IQVQXVFMNOFTMU-FLIBITNWSA-N
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-
Chemical Name	(3Z)-3-butylidene-4,5-dihydro-2-benzofuran-1-one
Synonyms	cis-Ligustilide; Ligustilide A
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage.(2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References

[1]. 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. [2]. 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. [3]. 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.

Additional Infomation

(Z)-ligustilide is a butenolide. It has a role as a metabolite. Ligustilide has been reported in Apiaceae, Angelica glauca, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO : ≥ 100 mg/mL (~525.65 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (13.14 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (13.14 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (13.14 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.2565 mL	26.2826 mL	52.5652 mL
	5 mM	1.0513 mL	5.2565 mL	10.5130 mL
	10 mM	0.5257 mL	2.6283 mL	5.2565 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.