1176877-34-1

Basic information

• Product Name: (-)-(1R,2S,4S)-cyclohexane-1,2,4-triol
• CAS NO: 1176877-34-1
• Molecular Weight: 132.159
• Mol File: 1176877-34-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (-)-(1R,2S,4S)-cyclohexane-1,2,4-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(1R,2S,4S)-cyclohexane-1,2,4-triol(1176877-34-1)
• EPA Substance Registry System: (-)-(1R,2S,4S)-cyclohexane-1,2,4-triol(1176877-34-1)

Safety Data

• Hazardous Substances Data: 1176877-34-1(Hazardous Substances Data)

Upstream product

• 626-02-8 3-Iodophenol 
• 1176877-26-1 (4R,5S)-4,5-dihydroxycyclohex-2-enone 

Relevant articles and documents

Enzyme-Catalysed Synthesis of Cyclohex-2-en-1-one cis-Diols from Substituted Phenols, Anilines and Derived 4-Hydroxycyclohex-2-en-1-ones

Toluene dioxygenase-catalysed cis-dihydroxylations of substituted aniline and phenol substrates, with a Pseudomonas putida UV4 mutant strain and an Escherichia coli pCL-4t recombinant strain, yielded identical arene cis-dihydrodiols, which were isolated as the preferred cyclohex-2-en-1-one cis-diol tautomers. These cis-diol metabolites were predicted by preliminary molecular docking studies, of anilines and phenols, at the active site of toluene dioxygenase. Further biotransformations of cyclohex-2-en-1-one cis-diol and hydroquinone metabolites, using Pseudomonas putida UV4 whole cells, were found to yield 4-hydroxycyclohex-2-en-1-ones as a new type of phenol bioproduct. Multistep pathways, involving ene reductase- and carbonyl reductase-catalysed reactions, were proposed to account for the production of 4-hydroxycyclohex-2-en-1-one metabolites. Evidence for the phenol hydrate tautomers of 4-hydroxycyclohex-2-en-1-one metabolites was shown by formation of the corresponding trimethylsilyl ether derivatives. (Figure presented.).

New families of enantiopure cyclohexenone cis-diol, o-quinol dimer and hydrate metabolites from dioxygenase-catalysed dihydroxylation of phenols

Toluene dioxygenase-catalysed cis-dihydroxylation of phenols has led to the discovery of new enantiopure cyclohexenone cis-diol, o-quinol dimer and phenol hydrate metabolites having synthetic potential.