Agricultural and Biological Chemistry
Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369
Studies on Chrysanthemic Acid
Part IVX. Oxidation Products from (±)-cis-Chrysathemic Acid
Masanao MATSUIHirosuke YOSHIOKA
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1964 Volume 28 Issue 1 Pages 32-37

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Abstract
One of oxidation products from (±)-cis-chrysanthemic acid with aqueous potassium permanganate was an acid melting at 243°C, which had been believed to be an isomer of (±)-cis-dihydroxydihydrochrysanthemic acids, but the structure of the acid was confirmed to be an acetal of (±)-cis-caronhalfaldehydic acid with (±)-cis-dihydroxydihydrochrysanthemic acid. On the other hand, an acid melting at 189°C was isolated from the same oxidation mixture, which afforded a lactol of (±)-cis-caronhalfaldehydic acid by the oxidation with aqueous periodic acid, and afforded (±)-cis-ketol-chrysanthemic acid by the oxidation with aqueous potassium permanganate.
(±)-cis-Ketol-chrysanthemic acid was converted to already known (±)-trans-ketol-chrysanthemic acid on heating with aqueous sodium hydroxide. Now the acid melting at 189°C was confirmed to be an isomer of (±)-cis-dihydroxydihydrochrysanthemic acid.
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