127156-28-9

Basic information

• Product Name: 2β-acetoxyclovan-9α(R)-ol
• CAS NO: 127156-28-9
• Molecular Weight: 280.408
• Mol File: 127156-28-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2β-acetoxyclovan-9α(R)-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2β-acetoxyclovan-9α(R)-ol(127156-28-9)
• EPA Substance Registry System: 2β-acetoxyclovan-9α(R)-ol(127156-28-9)

Safety Data

• Hazardous Substances Data: 127156-28-9(Hazardous Substances Data)

Upstream product

• 60594-23-2 4α,5α-epoxyisocaryophyllene 
• 2649-64-1 clovanediol 
• 108-24-7 acetic anhydride 

Relevant articles and documents

Constituents of Sindora sumatrana MIQ. II. Five new sesquiterpenoids from the dried pods

Further investigation of the neutral fraction of the methanolic extract of Sindora sumatrana MIQ. (Leguminosae) has yielded five new sesquiterpenoids: a new trans-isodaucane diol (1), two caryophyllane-type epoxydiols (2, 3), the diacetate of a caryophyllane-type trialcohol (4) and a caryolane-type hydroxy-ketone (5) which possesses an α-C-12 methano bridge. The structure elucidation of the compounds was based mainly on two-dimensional NMR techniques. The biosynthetic significance of the acid-catalyzed rearrangement of 5 to give a clovane-type hydroxyketone (10) is also discussed.

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.