WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H329885
CAS#: 1801433-90-8
Description: Biliatresone is an example of a very rare type of a naturally occurring isoflavonoid-related 1,2-diaryl-2-propenone found in Dysphania glomulifera and D. littoralis. It has been found to cause extrahepatic biliary atresia in a zebrafish model. The enone moiety of biliatresone is particularly reactive, being enhanced by the methylenedioxy, methoxy and hydroxy groups, and undergoes ready Michael addition of water and methanol.
Hodoodo Cat#: H329885
Name: Biliatresone
CAS#: 1801433-90-8
Chemical Formula: C18H16O6
Exact Mass: 328.09
Molecular Weight: 328.320
Elemental Analysis: C, 65.85; H, 4.91; O, 29.24
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Synonym: Biliatresone;
IUPAC/Chemical Name: 1-(4,6-dimethoxy-1,3-benzodioxol-5-yl)-2-(2-hydroxyphenyl)prop-2-en-1-one
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
SMILES Code: C=C(C1=CC=CC=C1O)C(C2=C(OC)C=C(OCO3)C3=C2OC)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 328.32 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Zhao X, Lorent K, Wilkins BJ, Marchione DM, Gillespie K, Waisbourd-Zinman O, So J, Koo KA, Shin D, Porter JR, Wells RG, Blair I, Pack M. Glutathione antioxidant pathway activity and reserve determine toxicity and specificity of the biliary toxin biliatresone in zebrafish. Hepatology. 2016 Sep;64(3):894-907. doi: 10.1002/hep.28603. Epub 2016 Jun 11. PubMed PMID: 27102575; PubMed Central PMCID: PMC5251204.
2: Waisbourd-Zinman O, Koh H, Tsai S, Lavrut PM, Dang C, Zhao X, Pack M, Cave J, Hawes M, Koo KA, Porter JR, Wells RG. The toxin biliatresone causes mouse extrahepatic cholangiocyte damage and fibrosis through decreased glutathione and SOX17. Hepatology. 2016 Sep;64(3):880-93. doi: 10.1002/hep.28599. Epub 2016 May 20. PubMed PMID: 27081925; PubMed Central PMCID: PMC4992464.
3: Koo KA, Waisbourd-Zinman O, Wells RG, Pack M, Porter JR. Reactivity of Biliatresone, a Natural Biliary Toxin, with Glutathione, Histamine, and Amino Acids. Chem Res Toxicol. 2016 Feb 15;29(2):142-9. doi: 10.1021/acs.chemrestox.5b00308. Epub 2016 Jan 13. PubMed PMID: 26713899; PubMed Central PMCID: PMC4757443.
4: Davenport M. Biliary atresia: From Australia to the zebrafish. J Pediatr Surg. 2016 Feb;51(2):200-5. doi: 10.1016/j.jpedsurg.2015.10.058. Epub 2015 Nov 4. Review. PubMed PMID: 26653951.
5: Koo KA, Lorent K, Gong W, Windsor P, Whittaker SJ, Pack M, Wells RG, Porter JR. 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. doi: 10.1021/acs.chemrestox.5b00227. Epub 2015 Jul 20. PubMed PMID: 26175131; PubMed Central PMCID: PMC4755499.
6: Patman G. Biliary tract: Newly identified biliatresone causes biliary atresia. Nat Rev Gastroenterol Hepatol. 2015 Jul;12(7):369. doi: 10.1038/nrgastro.2015.91. Epub 2015 May 26. PubMed PMID: 26008130.
7: Lorent K, Gong W, Koo KA, Waisbourd-Zinman O, Karjoo S, Zhao X, Sealy I, Kettleborough RN, Stemple DL, Windsor PA, Whittaker SJ, Porter JR, Wells RG, Pack M. Identification of a plant isoflavonoid that causes biliary atresia. Sci Transl Med. 2015 May 6;7(286):286ra67. doi: 10.1126/scitranslmed.aaa1652. PubMed PMID: 25947162; PubMed Central PMCID: PMC4784984.
