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The ability of Armillariella mellea to transform cyclic monoterpenic alcohols and their acetates

✍ Scribed by B. Draczyńska-Łusiak; Prof. Dr. A. Siewiński


Book ID
102388571
Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
419 KB
Volume
31
Category
Article
ISSN
0233-111X

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✦ Synopsis


An Armillariella mellea culture was found to transform trans-sobrerol to a very small extent, whereas menthol resisted its action altogether. Acetylation of both alcohols, on the other hand, reappointed their reactivity in the same A . rnellea culture. Thus, trans-sobrerol -monoacetate and menthyl acetate underwent a two-step transformation involving hydroxylation (preserving the acetate link) to 3-acetoxy-6,8-p-methen-diol and 8-hydroxymenthyl acetate, respectively, which were converted by hydrolysis to 3,6,8-p-menthen-trioI and 8-hydroxymenthol, respectively.

The transformation of racemic menthyl acetate was enantiospecific; (-) 8-hydroxymenthol that was formed after 21 days contained 98% of enantiomer l R , 3R, 4s.


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