Reaction mass of rel-{(1R,2S)-1-methyl-2-[(2R)-5-methylhex-4-en-2-yl]cyclopropyl}methanol and rel-{(1S,2R)-1-methyl-2-[(2R)-5-methylhex-4-en-2-yl]cyclopropyl}methanol

Adsorption / desorption

Link to relevant study record(s)

Reference

Endpoint:

adsorption / desorption: screening

Type of information:

experimental study

Adequacy of study:

key study

Study period:

June - July 2013

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

guideline study with acceptable restrictions

Qualifier:

according to guideline

Guideline:

OECD Guideline 121 (Estimation of the Adsorption Coefficient (Koc) on Soil and on Sewage Sludge using High Performance Liquid Chromatography (HPLC))

Version / remarks:

2001

Deviations:

no

Qualifier:

according to guideline

Guideline:

EU Method C.19 (Estimation of the Adsorption Coefficient (KOC) on Soil and Sewage Sludge Using High Performance Liquid Chromatography (HPLC))

Version / remarks:

2008

Deviations:

no

GLP compliance:

yes (incl. QA statement)

Type of method:

HPLC estimation method

Media:

other: Separation on HPLC column with Reference Substances - simulates soil and sewage sludge

Specific details on test material used for the study:

GR-50-1408 is the Givaudan identification code which was employed for ROSYFOLIA during the early, developmental and testing period.

Radiolabelling:

no

Test temperature:

HPLC column at 35 °C during separation.
The determination was performed at 35 °C (temperature of the column), but the value obtained above can be considered to represent the value at an unspecified, probably ambient temperature since no mention is made in the guidelines of the temperature at which the tabulated reference substances log Koc values were determined. Adsorption coefficients of the test and reference substances are assumed to vary with temperature in the same way.

Details on study design: HPLC method:

Reverse phase High Performance Liquid Chromatography on cyanopropyl-modified silicia stationary phase containing lipophilic and polar moieties, is used.

While passing through the column among with the mobile phase the test substance interacts with the stationary phase. As a result of the partitioning between the mobile and stationary phase the test substance is retarded. The dual-composition of the stationary phase having polar and non-polar sites allows for interaction of polar and non-polar groups of a molecule in a similar way as it is the case for organic matter in soil or sewage sludge matrices. This enables the relationship between the retention time on the column and the adsorption coefficient on organic matter to be established.

A solution of the test substance was prepared (10.0 mg in 25 ml methanol/water 55/45 v/v).

After equilibration of the HPLC system, the calibration mixture was injected first, followed by the test chemical solution twice and the calibration mixture again.

Retention times were measures and averaged and the decimal logarithms of the capacity factors k were calculated. The linear regression parameters of the relationship
log Koc = f(log k)
were also calculated from the data obtained with the calibration mixture and, therewith, log Koc of the test substance was determined from its measured capacity factor.

Finally, solutions of the reference substances were injected individually to confirm the peak assignment.

Details on test conditions:

Equipment
Perkin Elmer (series 200) HPLC system comprising:
- high pressure pump
- auto-sampler
- column compartment
- refractive index detector

Column - 250mm x 4.6mm, Nucleodur® 100-5 CN-RP (Macherey-Nagel)
Mobile phase: methanol / water 55/45 (v/v))
Flow rate: 1.0 ml/min
Column temp: 35°C
Injected volume: 100 µl

Type:

log Koc

Value:

3.41

Temp.:

35 °C

Matrix:

HPLC approach (OECD 121)

Remarks on result:

other: Peak 3 - minor component (5.4% of surface area)

Type:

log Koc

Value:

2.89

Temp.:

35 °C

Matrix:

HPLC approach (OECD 121)

Remarks on result:

other: Peak 1 - minor component (2.5% by surface area)

Key result

Type:

log Koc

Value:

3.14

Temp.:

35 °C

Matrix:

HPLC approach (OECD 121)

Remarks on result:

other: Peak 2 - major component (92.1% by surface area)

Details on results (HPLC method):

Detailed results are given in appendix 1 and illustrated by the graph in appendix 2 of the attached study report.

The chromatograms of GR-50-1408 show three peaks at average retention times of 5.28 minutes (~2.5% peak area, can be assigned to non-cyclopropanates products present in the batch tested); the main peak 5.76 minutes (~92.1% peak area) and 6.45 minutes (~5.4% peak area) corresponding to adsorption coefficients (log value) of 2.89, 3,14 and 3.41.
Therefore Adsorption coefficient of (Koc) of GR-50-1408:
Log Koc = 3.14

Validity criteria fulfilled:

yes

Conclusions:

The chromatograms of GR-50-1408 show three peaks at average retention times of 5.28 minutes (~2.5% peak area, can be assigned to non-cyclopropanates products present in the batch tested); the main peak 5.76 minutes (~92.1% peak area) and 6.45 minutes (~5.4% peak area) corresponding to adsorption coefficients (log value) of 2.89, 3,14 and 3.41.
Therefore Adsorption coefficient of (Koc) of GR-50-1408:

Log Koc = 3.14 / Koc = 1380

Executive summary:

The adsorption coefficient of (Koc) on soil and on sewage sludge of GR-50-1408 was determined by the Reverse Phase High Performance Liquid Chromatographic Method according to the OECD Guidelines for Testing of Chemicals Method No 121.

The result is:

Adsorption coefficient of (Koc) of GR-50-1408:

Log Koc = 3.14

Description of key information

 

The adsorption coefficient of (Koc) on soil and on sewage sludge of GR-50-1408 was determined by the Reverse Phase High Performance Liquid Chromatographic Method according to the OECD Guidelines for Testing of Chemicals Method No 121.

The result is:

Adsorption coefficient of (Koc) of GR-50-1408:

Log Koc = 3.14 / Koc = 1380

Key value for chemical safety assessment

Koc at 20 °C:

1 380