Biliatresone is a natural toxin extracted from the algae Dysphania glomulifera and D. littoralis. Biliatresone is a 1,2-diaryl-2-propanone isoflavone that produces extrahepatic biliary atresia in a zebrafish model.

Physicochemical Properties

Molecular Formula	C18H16O6
Molecular Weight	328.316045761108
Exact Mass	328.094
CAS #	1801433-90-8
PubChem CID	124079379
Appearance	White to yellow viscous liquid
LogP	3.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	5
Heavy Atom Count	24
Complexity	478
Defined Atom Stereocenter Count	0
InChi Key	SIKIIXNKUAAGAM-UHFFFAOYSA-N
InChi Code	InChI=1S/C18H16O6/c1-10(11-6-4-5-7-12(11)19)16(20)15-13(21-2)8-14-17(18(15)22-3)24-9-23-14/h4-8,19H,1,9H2,2-3H3
Chemical Name	1-(4,6-dimethoxy-1,3-benzodioxol-5-yl)-2-(2-hydroxyphenyl)prop-2-en-1-one
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
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

ln Vitro	Primary cilia can be reduced by bilitresone, and microtubule stability can be observed in a number-dependent manner, suggesting that bilitresone can decrease the microtubule stability of primary newborn extrahepatic bile ducts [1]. In mice, biliatresone (2 μg/mL) causes anomalies in the cholangiocytes and ruptures the spheroid lumen [1].
ln Vivo	In zebrafish experiments, the lethal dose of Biliatresone was found to be 1 μg/mL. Biliatresone is toxic at levels between 0.065 and 1.0 μg/mL and is dramatically reduced at higher concentrations [1]. The larvae treated with modest dosages at 5 dpf [0.0625 μg/mL (0.2 μM) and 0.125 μg/mL (0.4 μM)] only displayed severe gallbladder problems, while the larvae treated with the prior group clearly displayed morphological defects related to the gallbladder and extrahepatic ducts [1].
References	[1]. Biliatresone, a Reactive Natural Toxin From Dysphania Glomulifera and D. Littoralis: Discovery of the Toxic Moiety 1,2-Diaryl-2-Propenone. Chem Res Toxicol. 2015 Aug 17;28(8):1519-21. [2]. Identification of a Plant Isoflavonoid That Causes Biliary Atresia. Sci Transl Med. 2015 May 6;7(286):286ra67.
Additional Infomation	Biliatresone is a member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted at positions 5 by a 2-(2-hydroxyphenyl)-3-oxoprop-1-en-3-yl group and at positions 4 and 6 by methoxy groups. A very rare type of isoflavonoid-related 1,2-diaryl-2-propenone found in Dysphania glomulifera (red crumbweed) and D. littoralis, the enone moiety is particularly reactive, undergoing ready Michael addition of water and methanol. Biliatresone has been found to cause extrahepatic biliary atresia (obliteration or discontinuity of the extrahepatic biliary system, resulting in obstruction to bile flow) in a zebrafish model. It has a role as a toxin and a plant metabolite. It is a member of benzodioxoles, an enone, an aromatic ketone, an aromatic ether and a member of phenols.

Solubility Data

Solubility (In Vitro)

DMSO : ~50 mg/mL (~152.29 mM)

Solubility (In Vivo)

Solubility in Formulation 1: 2 mg/mL (6.09 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.0 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 mg/mL (6.09 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 20.0 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 mg/mL (6.09 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 20.0 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	3.0458 mL	15.2290 mL	30.4581 mL
	5 mM	0.6092 mL	3.0458 mL	6.0916 mL
	10 mM	0.3046 mL	1.5229 mL	3.0458 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.