Synthesis of enantiomeric menthol derivatives for forming and probing chiral surfaces. X-ray crystal and molecular structures of (+)-(1S,2R,5S)-1-(2-tricyanovinyl-1H-pyrrol-1-yl-methoxy)-2-isopropyl-5-methylcyclohexane

Cattaruzza, Fabrizio; Fares, Vincenzo; Flamini, Alberto; Prosperi, T.

doi:10.1016/j.tetasy.2006.04.016

Cited by 2 publications

(1 citation statement)

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“…Among them, l-menthol is not only one of the most important flavoring chemicals used extensively in oral products, pharmaceuticals, tobacco products, confectionaries, and shaving products [1,2], but also a useful chiral resolving reagent [3,4]. In the past two decades, the global demand for l-menthol increased sharply from 6,300 to 20,000 t [5], and the production of l-menthol by extracting from mint can no longer meet the market demands.…”

Section: Introductionmentioning

confidence: 99%

Efficient production of l-menthol in a two-phase system with SDS using an immobilized Bacillus subtilis esterase

Pan

Dang

Zheng

et al. 2014

Bioresour. Bioprocess.

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Background: levo-Menthol is an important flavoring chemical, which can be prepared by enantioselective enzymatic hydrolysis of dl-menthyl esters. A recombinant esterase (BsE) cloned from Bacillus subtilis 0554 shows excellent enantioselectivity to dl-menthyl acetate and has been immobilized using cross-linked enzyme aggregates. Though BsE has relatively high substrate tolerance, the conversion of dl-menthyl acetate decreased sharply with the increase of substrate loading from 1 to 3 M in mono-aqueous system, which might be due to the severe inhibition of enzyme activity at extremely high load of substrate or product. In this work, enzymatic hydrolysis of dl-menthyl acetate with an extremely high load using the immobilized CLEA-BsE was investigated in an organic-aqueous biphasic system containing surfactant to establish a promising bioprocess for large-scale production of l-menthol. Results: An efficient biphasic reaction system of pentanol-water containing sodium dodecyl sulfate (SDS) was developed for improving enantioselective hydrolysis of dl-menthyl acetate to produce l-menthol by immobilized BsE. Under the optimized reaction conditions, l-menthol was produced in >97% enantiomeric excess (ee) at a substrate load of up to 3.0 M with >40% conversion. Conclusions: All the positive features demonstrate the potential applicability of the bioprocess for the large-scale production of l-menthol.

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Section: Introductionmentioning

confidence: 99%