Document Detail


Synthesis of omega 9-tetracosynoic and omega 9-octacosynoic acids as entries into tritiated metabolic precursors of cis-9-tricosene and cis-9-heptacosene in the housefly.
MedLine Citation:
PMID:  2093144     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The syntheses of 15-tetracosynoic acid (omega 9-tetracosynoic acid) and 19-octacosynoic acid (omega 9-octacosynoic acid) are described. These alkynoic acids are to be tritiated to the corresponding alkenoic acids, which will be used as metabolic precursors of housefly pheromone components. The final step in each synthesis involved the coupling of 1-decyne to the lithio-salt of the appropriate omega-bromoacid. Homologation of dibromoalkanes was accomplished with triphasic catalytic displacement of bromide by cyanide ion. Oxidation of a bromo-alcohol to a bromoacid was performed in benzene with KMnO4 and 18-crown-6 ether.
Authors:
J G Pomonis; H Hakk
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Lipids     Volume:  25     ISSN:  0024-4201     ISO Abbreviation:  Lipids     Publication Date:  1990 Dec 
Date Detail:
Created Date:  1991-06-19     Completed Date:  1991-06-19     Revised Date:  2003-11-14    
Medline Journal Info:
Nlm Unique ID:  0060450     Medline TA:  Lipids     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  821-6     Citation Subset:  IM    
Affiliation:
Insect Biochemistry and Physiology, ARS-USDA, Fargo, North Dakota 58105.
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MeSH Terms
Descriptor/Qualifier:
Alkenes / chemistry*
Animals
Fatty Acids, Monounsaturated / chemistry*
Houseflies / metabolism*
Pheromones / chemistry*
Chemical
Reg. No./Substance:
0/Alkenes; 0/Fatty Acids, Monounsaturated; 0/Pheromones; 132861-77-9/15-tetracosynoic acid; 138898-74-5/19-octacosynoic acid; 36258-12-5/9-heptacosene; 52078-48-5/muscalure

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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