TERPENOIDS: II. CEANOTHENIC ACID: A C29 A-NORLUPANE DERIVATIVE
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Extraction of Ceanothus americanus (Jersey Tea) has afforded a new pentacyclic triterpenoid of the empirical formula C29H42O4. It is a dicarboxylic acid containing two ethylenic linkages. The environment of one carboxyl group and one ethylenic linkage has been shown by diagnostic transformations characteristic of ring E of the lupeol–betulin series. The other ethylenic linkage has been shown to be present in a contracted ring A from which one carbon atom has been lost. The position of the second carboxyl group has been established by introduction of the 11-oxo-12-ene system, when monodecarboxylation occurred under mild conditions. This and other evidence establishes ceanothenic acid to be A-norlupa-1,22-diene-14,17-dicarboxylic acid.
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2012 ◽
Vol 4
(6)
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pp. 319-330
2005 ◽
Vol 8
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pp. 878-881
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1964 ◽
Vol 19
(9)
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pp. 781-783
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1964 ◽
Vol 16
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pp. 298-305
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1934 ◽
Vol 59
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pp. 751-768
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