Isopropanol → Citronellal

HRID 1644156Notes

Reaction equation

HRID 1644156 reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][C:7](=[CH:9][CH:10]=[O:11])[CH3:8])[CH3:3].C(O)(C)C>C1(C)C=CC=CC=1>[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][CH:7]([CH2:9][CH:10]=[O:11])[CH3:8])[CH3:3]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 88433,7-Dimethylocta-2,6-Dienal2×

Product 1

HCID 7794Citronellal

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prior to the biotransformation, 0.5 ml of permeabilized cells were vortexed with 0.15 ml toluene in 2 ml screw capped glass vials and incubated for 10 min at room temperature. The other components were then added to give 1 ml of aqueous phase with the same composition as the aqueous/NADPH system, with only citral and isopropanol omitted. The reaction was started by addition of 0.05 ml of 0.4 M citral in toluene and the vials were turned vertically on a wheel at 30° C. After 3 h the complete sample was extracted with 0.4 ml freshly prepared solution of 0.15% [v/v] 1-octanol (internal GC standard) in chloroform. After centrifugation 0.4 ml of the lower organic phase (toluene/chloroform mixture) was removed for GC analysis. Strains that formed citronellal were compared in a toluene and a methyl tertiary-butylether (MTBE) two-phase system as detailed below.

Workup

  1. customwere turned vertically on a wheel at 30° C
  2. extractionAfter 3 h the complete sample was extracted with 0.4 ml freshly prepared solution of 0.15% [v/v] 1-octanol (internal GC standard) in chloroform
  3. customAfter centrifugation 0.4 ml of the lower organic phase (toluene/chloroform mixture) was removed for GC analysis

Sources & evidence

ORD record
ord-2c12195641a940d2ba0fe90beb7e92fc
Source dataset
uspto-grants-2012_02
Patent number
US08124387B2

Reaction notes

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