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Wikipedia

Biliatresone

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.[1][2][3] 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,[4] and undergoes ready Michael addition of water and methanol.

Biliatresone
Names
Preferred IUPAC name
1-(4,6-Dimethoxy-2H-1,3-benzodioxol-5-yl)-2-(2-hydroxyphenyl)prop-2-en-1-one
Identifiers
  • 1801433-90-8 N
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:131631 Y
ChemSpider
  • 58827638 Y
  • 124079379
  • 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
    Key: SIKIIXNKUAAGAM-UHFFFAOYSA-N
  • O=C(C(C1=C(O)C=CC=C1)=C)C2=C(OC)C3=C(OCO3)C=C2OC
Properties
C18H16O6
Molar mass 328.320 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is YN ?)

References edit

  1. ^ Lorent, K.; et al. (May 2015). "Identification of a plant isoflavonoid that causes biliary atresia". Sci Transl Med. 7 (286): 286ra67. doi:10.1126/scitranslmed.aaa1652. PMC 4784984. PMID 25947162.
  2. ^ Koo, K.A.; et al. (Aug 2015). "Biliatresone, a Reactive Natural Toxin from Dysphania glomulifera and D. littoralis: Discovery of the Toxic Moiety 1,2-Diaryl-2-Propenone". Chem Res Toxicol. 28 (8): 1519–1521. doi:10.1021/acs.chemrestox.5b00227. PMC 4755499. PMID 26175131.
  3. ^ Patman, G. (2015). "Biliary tract: Newly identified biliatresone causes biliary atresia". Nat Rev Gastroenterol Hepatol. 12 (7): 369. doi:10.1038/nrgastro.2015.91. PMID 26008130. S2CID 205488639.
  4. ^ Koo, K.A.; et al. (2016). "Reactivity of biliatresone, a natural biliary toxin, with glutathione, histamine, and amino acids". Chem. Res. Toxicol. 29 (2): 142–9. doi:10.1021/acs.chemrestox.5b00308. PMC 4757443. PMID 26713899.

biliatresone, example, very, rare, type, naturally, occurring, isoflavonoid, related, diaryl, propenone, found, dysphania, glomulifera, littoralis, been, found, cause, extrahepatic, biliary, atresia, zebrafish, model, enone, moiety, biliatresone, particularly,. 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 1 2 3 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 4 and undergoes ready Michael addition of water and methanol Biliatresone NamesPreferred IUPAC name 1 4 6 Dimethoxy 2H 1 3 benzodioxol 5 yl 2 2 hydroxyphenyl prop 2 en 1 oneIdentifiersCAS Number 1801433 90 8 N3D model JSmol Interactive imageChEBI CHEBI 131631 YChemSpider 58827638 YPubChem CID 124079379InChI 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 3H3Key SIKIIXNKUAAGAM UHFFFAOYSA NSMILES O C C C1 C O C CC C1 C C2 C OC C3 C OCO3 C C2OCPropertiesChemical formula C 18H 16O 6Molar mass 328 320 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N what is Y N Infobox referencesReferences edit Lorent K et al May 2015 Identification of a plant isoflavonoid that causes biliary atresia Sci Transl Med 7 286 286ra67 doi 10 1126 scitranslmed aaa1652 PMC 4784984 PMID 25947162 Koo K A et al Aug 2015 Biliatresone a Reactive Natural Toxin from Dysphania glomulifera and D littoralis Discovery of the Toxic Moiety 1 2 Diaryl 2 Propenone Chem Res Toxicol 28 8 1519 1521 doi 10 1021 acs chemrestox 5b00227 PMC 4755499 PMID 26175131 Patman G 2015 Biliary tract Newly identified biliatresone causes biliary atresia Nat Rev Gastroenterol Hepatol 12 7 369 doi 10 1038 nrgastro 2015 91 PMID 26008130 S2CID 205488639 Koo K A et al 2016 Reactivity of biliatresone a natural biliary toxin with glutathione histamine and amino acids Chem Res Toxicol 29 2 142 9 doi 10 1021 acs chemrestox 5b00308 PMC 4757443 PMID 26713899 Retrieved from https en wikipedia org w index php title Biliatresone amp oldid 1121378002, wikipedia, wiki, book, books, library,

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