| Synthesis of anacardic acids, 6-[8(Z),11(Z)-pentadecadienyl]salicylic acid and 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid. | |
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MedLine Citation:
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PMID: 11201219 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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11-Chloro-3-methoxy-2-undecenal was synthesized from 8-bromooctanol, and an annelation reaction with this aldehyde and ethyl acetoacetate proceeded to give the ethyl 6-(8-chlorooctyl)salicylate. Ethyl 6-(8-chlorooctyl)salicylate was converted to ethyl 6-(7-formylheptyl)-2-methoxybenzoate through the iodide after protection of the phenolic hydroxyl group. Finally, the Wittig reaction with the aldehyde and triphenylphosphonium iodides in the presence of BuLi gave the methoxybenzoates, and then treatments of these methoxybenzoates with BBr3 in CH2Cl2 and 10% NaOH in ethanol gave 6-18(Z),11(Z)-pentadecadienyllsalicylic acid (anacardic acid 3) and 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid (anacardic acid 4) which were isolated from plants of the anacardiaceae. |
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Authors:
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M Satoh; N Takeuchi; T Nishimura; T Ohta; S Tobinaga |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Chemical & pharmaceutical bulletin Volume: 49 ISSN: 0009-2363 ISO Abbreviation: Chem. Pharm. Bull. Publication Date: 2001 Jan |
Date Detail:
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Created Date: 2001-01-26 Completed Date: 2001-03-29 Revised Date: 2004-11-17 |
Medline Journal Info:
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Nlm Unique ID: 0377775 Medline TA: Chem Pharm Bull (Tokyo) Country: Japan |
Other Details:
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Languages: eng Pagination: 18-22 Citation Subset: IM |
Affiliation:
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Showa Pharmaceutical Univercity, Machida, Tokyo, Japan. ms@ac.shoyaku.ac.jp |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Alkenes
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chemical synthesis* Anacardic Acids* Salicylic Acids / chemical synthesis* Spectrum Analysis |
| Chemical | |
Reg. No./Substance:
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0/6-(8,11,14-pentadecadienyl)salicylic acid; 0/6-(8,11-pentadecadienyl)salicylic acid; 0/Alkenes; 0/Anacardic Acids; 0/Salicylic Acids; 18654-18-7/anacardic acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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