2649-64-1

Usage

Uses

Clovanediol is a natural product found in cloves and other plant species.

Upstream product

• 1139-30-6 Caryophyllene oxide 
• 60594-23-2 4α,5α-epoxyisocaryophyllene 
• 1139-30-6 caryophyllene oxide 
• 100-53-8 phenylmethanethiol 
• 103475-43-0 caryophyllene-1β,10α-epoxide 

Downstream Products

• 2649-68-5 (1S,2S,5S,8R,9R)-2,9-diacetoxyclovane 
• 127156-28-9 2β-acetoxyclovan-9α(R)-ol 

Relevant academic research and scientific papers

Synthesis and oxidation of sulfides based on caryophyllene oxide and phenylmethanethiol

Lewis acid-catalyzed reaction of (–)-caryophyllene oxide with phenylmethanethiol gave sulfides with clovane and caryophyllane structure which were oxidized to the corresponding sulfoxides and sulfones in 74 and 84% yield, respectively.

MOLECULAR REARRANGEMENTS OF CARYOPHYLLENE AND ISOCARYOPHYLLENE 4,5-EPOXIDES IN SUPERACIDIC MEDIA

Enantiomeric stable carbocations were generated from the epimeric pair of optically active isocaryophyllene 4β,5β- and 4α,5α-epoxides in the superacid.The subsequent molecular rearrangement path is determined by participation of the ? and ? bonds in opening of the epoxide ring.For the case of caryophyllene 4β,5α- and 4α,5β-epoxides it was shown that rearrangement to compounds with the clovane or caryolane skeleton respectively is possible.The rearrangement of a compound of the caryophyllane type to compounds of the selinane group was realized for the first time.For the case of caryophyllene 4β,5α-epoxide it was shown that the generation temperature of the ions has a significant effect on the preferred position of the cationic center.

REARRANGED CARYOPHYLLENES BY BIOTRANSFORMATION WITH CHAETOMIUM COCHLIODES

Biotransformation of caryophyllene by Chaetomium cochliodes DSM 1909 (=ATCC 10195) leads to 4,5-epoxy-caryophyllene-7,12-diol as the main product.The hydroxylation of the geminal methyl groups is not very stereospecific, but as with Diploida gossypina the main product possesses the 11R-configuration.Side-reactions are ring contraction or formation of clovanes, probably via epoxide rearrangements.The use of mono- or diepoxy-caryophyllene as the substrate does not increase the yields significantly.Instead, diepoxy-caryophyllene gave a punctatin derivative.The same molecular framework, but with a different configuration, was observed among the fermentation products from Diplodia gossypina, which supports the assumption that a caryophyllane is the precursor of this class of antibiotics.