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MedKoo Cat#: 329885 | Name: Biliatresone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Biliatresone
Biliatresone
CAS#1801433-90-8

Theoretical Analysis

MedKoo Cat#: 329885

Name: Biliatresone

CAS#: 1801433-90-8

Chemical Formula: C18H16O6

Exact Mass: 328.0947

Molecular Weight: 328.32

Elemental Analysis: C, 65.85; H, 4.91; O, 29.24

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
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

Preparing Stock Solutions

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.

Recalculate based on batch purity %
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
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.