Registration Dossier

Administrative data

Endpoint:
additional ecotoxicological information
Type of information:
experimental study
Adequacy of study:
supporting study
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: Experimental results from a study according to acceptable scientific standards and reported in a peer-reviewed journal

Data source

Reference
Reference Type:
publication
Title:
Asymmetric synthesis of both enantiomers of secondary alcohols by reduction with a single microbe
Author:
Nakamura K, Takenaka K, Fujii M, Ida Y
Year:
2002
Bibliographic source:
Tetrahedron Letters 43, 3629-3631

Materials and methods

Principles of method if other than guideline:
To obtain the (S)-alcohol, cells from the microbe Geotrichum candidum IFO 5767 were cultivated in glycerol medium for 24 hours, then filtered from the growth medium and then mixed with the test substance, the polymer XAD-7 and water (15 g wet weight cells, 300 mg test substance, 18 g polymer, 90 mL water). The test mixture was shaken at 130 rpm for 1 day at 30 °C under a nitrogen atmosphere. To obtain the (R)-alcohol, cells from the same microbe (20 g wet weight) were mixed with the test substance (200 mg) and water (100 mL) in an open Sakaguchi flask. The test mixture was shaken at 130 rpm for 1 day at 30 °C.
GLP compliance:
no
Type of study / information:
Experiment to obtain alcohols from ketones by reduction with a single microbe

Test material

Constituent 1
Chemical structure
Reference substance name:
4-phenylbutan-2-one
EC Number:
219-847-4
EC Name:
4-phenylbutan-2-one
Cas Number:
2550-26-7
Molecular formula:
C10H12O
IUPAC Name:
4-phenylbutan-2-one
Details on test material:
not reported

Results and discussion

Any other information on results incl. tables

The first method yielded 98% (S)-alcohol with an enantiomeric purity of >99%. The second method yielded 61% (R)-alcohol with an enantiomeric purity of 85%.

Applicant's summary and conclusion

Conclusions:
The microbe Geotrichum candidum reduces the substance 4-phenylbutan-2-one to alcohol with the help of enzymes. The degree of biotransformation is high under aerobic and anaerobic conditions.
Executive summary:

The biotransformation of the substance 4-phenylbutan-2-one by the microbe Geotrichum candidum was studied both under aerobic and anaerobic conditions. To obtain the (S)-alcohol, cells from the microbe Geotrichum candidum IFO 5767 were cultivated in glycerol medium for 24 hours, then filtered from the growth medium and then mixed with the test substance, the polymer XAD-7 and water (15 g wet weight cells, 300 mg test substance, 18 g polymer, 90 mL water). The test mixture was shaken at 130 rpm for 1 day at 30 °C under a nitrogen atmosphere. To obtain the (R)-alcohol, cells from the same microbe (20 g wet weight) were mixed with the test substance (200 mg) and water (100 mL) in an open Sakaguchi flask. The test mixture was shaken at 130 rpm for 1 day at 30 °C.

The first method yielded 98% (S)-alcohol with an enantiomeric purity of >99%. The second method yielded 61% (R)-alcohol with an enantiomeric purity of 85%.