5793-28-2

Upstream product

• 60594-23-2 4α,5α-epoxyisocaryophyllene 
• 2649-65-2 Isocaryolanediol 
• 87-44-5 β-caryophyllene 
• 79236-30-9 (1S,2R,5R,8R)-1-Hydroxy-4,4,8-trimethyl-tricyclo[6.3.1.0^2,5]dodecan-9-one 

Downstream Products

• 2649-65-2 (1S,2R,5R,8R,9S)-4,4,8-Trimethyl-tricyclo[6.3.1.0^2,5]dodecane-1,9-diol 

Relevant academic research and scientific papers

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.