| Acid and base-catalyzed hydrolysis of bisphenol A-related compounds. | |
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MedLine Citation:
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PMID: 11219095 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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In order to ascertain whether an estrogenic bisphenol A is produced from bisphenol A-related monomers by chemical-induced hydrolysis and to clarify their hydrolytic mechanisms, bisphenol A dimethacrylate (Bis-DMA) and bisphenol A bis(glycidyl methacrylate) (Bis-GMA) were reacted with phosphoric acid, hydrochloric acid, and sodium hydroxide in methanol or methanol/water mixed media at 37 degrees C. Amounts of monomethacrylate intermediates as well as bisphenol A (BPA) were determined by the use of high-performance liquid chromatography (HPLC), and time-conversion curves of hydrolytic products were prepared. BPA and bisphenol A monomethacrylate were produced by acid-catalyzed hydrolysis of Bis-DMA. Bis-GMA was partly converted into monomethacrylate by phosphoric acid and into monomethacrylate and 2,2-bis[4-(2,3-dihydroxypropoxy) phenyl]propane (BHP) by hydrochloric acid. Hydrolytic reactions by sodium hydroxide were completed almost within 1 day, resulting in the production of BPA from Bis-DMA, and BHP from Bis-GMA. No BPA was formed from Bis-GMA by chemical-induced hydrolysis. The hydrolytic behaviors of these monomers were discussed. |
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Authors:
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Y Kadoma; M Tanaka |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Dental materials journal Volume: 19 ISSN: 0287-4547 ISO Abbreviation: Dent Mater J Publication Date: 2000 Jun |
Date Detail:
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Created Date: 2001-02-21 Completed Date: 2001-03-29 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 8309299 Medline TA: Dent Mater J Country: Japan |
Other Details:
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Languages: eng Pagination: 139-52 Citation Subset: D |
Affiliation:
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Department of Applied Functional Molecules, Division of Biofunctional Molecules, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10, Kanda-surugadai, Chiyoda-ku, Tokyo 101-0062, Japan. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Benzhydryl Compounds
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chemical synthesis Bisphenol A-Glycidyl Methacrylate / chemistry* Chromatography, High Pressure Liquid Estrogens, Non-Steroidal / chemical synthesis* Hydrochloric Acid / chemistry Hydrolysis Methacrylates / chemical synthesis, chemistry Models, Chemical Molecular Structure Phenols / chemical synthesis* Phosphoric Acids / chemistry Propane / analogs & derivatives, chemical synthesis Sodium Hydroxide / chemistry |
| Chemical | |
Reg. No./Substance:
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0/2,2-bis(4-(2,3-dihydroxypropoxy)phenyl)propane; 0/Benzhydryl Compounds; 0/Estrogens, Non-Steroidal; 0/Methacrylates; 0/Phenols; 0/Phosphoric Acids; 1310-73-2/Sodium Hydroxide; 1565-94-2/Bisphenol A-Glycidyl Methacrylate; 3253-39-2/2,2-di(4-methacryloxyphenyl)propane; 74-98-6/Propane; 7647-01-0/Hydrochloric Acid; 7664-38-2/phosphoric acid; 80-05-7/bisphenol A |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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