Caryophyllene, Reaction product with Acetic anhydride and acetic acid

Water solubility

Administrative data

Endpoint:

water solubility

Type of information:

experimental study

Adequacy of study:

key study

Study period:

May 12 - September 26, 2017

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Data source

Reference

Reference Type:

study report

Title:

Unnamed

Year:

2017

Report date:

2017

Materials and methods

Test guideline

Qualifier:

according to guideline

Guideline:

OECD Guideline 105 (Water Solubility)

GLP compliance:

yes (incl. QA statement)

Type of method:

other: the slow stirring experiment method

Test material

Test material information

Constituent 1

Reference substance name:

[1R-(1α,2α,5β,8β)]-4,4,8-trimethyltricyclo[6.3.1.02,5]dodecan-1-yl acetate

EC Number:

260-555-1

EC Name:

[1R-(1α,2α,5β,8β)]-4,4,8-trimethyltricyclo[6.3.1.02,5]dodecan-1-yl acetate

Cas Number:

57082-24-3

Molecular formula:

C17H28O2

IUPAC Name:

4,4,8-trimethyltricyclo[6.3.1.0~2,5~]dodec-1-yl acetate

Constituent 2

Reference substance name:

1-((1S,2S,5R)-1,4,4-trimethyltricyclo[6.3.1.02,5]dodec-8-en-9-yl)ethan-1-one

Molecular formula:

C17H26O

IUPAC Name:

1-((1S,2S,5R)-1,4,4-trimethyltricyclo[6.3.1.02,5]dodec-8-en-9-yl)ethan-1-one

Constituent 3

Reference substance name:

(3S,3aS,7R,9aS)-1,1,7-trimethyldecahydro-3a,7-methanocyclopenta[8]annulen-3-yl acetate

Cas Number:

77346-43-1

Molecular formula:

C17H28O2

IUPAC Name:

(3S,3aS,7R,9aS)-1,1,7-trimethyldecahydro-3a,7-methanocyclopenta[8]annulen-3-yl acetate

Constituent 4

Reference substance name:

1-((1S,2S,5R,9S)-1,4,4-trimethyltricyclo[6.3.1.02,5]dodec-7-en-9-yl)ethan-1-one

Cas Number:

Not applicable

Molecular formula:

C17H26O

IUPAC Name:

1-((1S,2S,5R,9S)-1,4,4-trimethyltricyclo[6.3.1.02,5]dodec-7-en-9-yl)ethan-1-one

Constituent 5

Reference substance name:

4,4,8-trimethyltricyclo[6.3.1.02,5]dodecan-1-ol

EC Number:

207-458-2

EC Name:

4,4,8-trimethyltricyclo[6.3.1.02,5]dodecan-1-ol

Cas Number:

472-97-9

Molecular formula:

C15H26O

IUPAC Name:

4,4,8-trimethyltricyclo[6.3.1.0~2,5~]dodecan-1-ol

Constituent 6

Reference substance name:

(3S,3aS,7R,9aS)-1,1,7-trimethyldecahydro-3a,7-methanocyclopenta[8]annulen-3-ol

Cas Number:

62560-57-0

Molecular formula:

C15H26O

IUPAC Name:

(3S,3aS,7R,9aS)-1,1,7-trimethyldecahydro-3a,7-methanocyclopenta[8]annulen-3-ol

Constituent 7

Reference substance name:

2,2,4,7a-tetramethyl-1,2,3,6,7,7a-hexahydro-1,3a-ethanoindene

Cas Number:

4545-68-0

Molecular formula:

C15H24

IUPAC Name:

2,2,4,7a-tetramethyl-1,2,3,6,7,7a-hexahydro-1,3a-ethanoindene

Constituent 8

Reference substance name:

not applicable

Cas Number:

not applicable

Molecular formula:

not applicable

IUPAC Name:

not applicable

Test material form:

liquid

Specific details on test material used for the study:

Name (as stated in the report): VETYNAL
Batch: VE00473596
Expiration date: March 05, 2019

Results and discussion

Water solubility

Water solubility 1

Key result

Water solubility:

0.981 mg/L

Conc. based on:

test mat.

Incubation duration:

48 h

Temp.:

20 °C

pH:

5.51

Remarks on result:

other: loading rate 118 to 132 mg test item/L

Water solubility 2

Water solubility:

0.598 mg/L

Conc. based on:

test mat.

Incubation duration:

48 h

Temp.:

20 °C

pH:

5.49

Remarks on result:

other: loading rate of 13 to 15 mg test item/L

Details on results:

The determination of the water solubility of VETYNAL was performed based on the OECD Guideline for the Testing of Chemicals, No. 105: Water Solubility, and adapted to a slow stirring design for test items which could form an emulsion due to their physical properties.

After a stirring time of 24 hours, 48 hours and 72 hours at 30 °C, the samples were equilibrated for another 24 hours at 20 °C. Afterwards, the samples were taken through a tap at the bottom of the flask, extracted with internal standard solution and analyzed by GC with FID detection.

According to the test guideline, the result found after a defined incubation time should not differ by more than 15 % from the result found after a shorter incubation time. The concentrations measured after 72 hours did not exceed by more than 15 % the concentration measured after an
incubation time of 48 hours for both loading rates. The acceptance criterium was thereforefulfilled and the saturation was achieved after 48 hours. The study is therefore valid.

For the loading rate of 13 to 15 mg test item/L, the water solubility of VETYNAL at 20 °C was
found to be 0.598 ± 0.050 mg/L, at a mean pH value of 5.49.
For the loading rate 118 to 132 mg test item/L, the water solubility of VETYNAL at 20 °C was 0.981 ± 0.057 mg/L, at mean pH value of 5.51.

The results of the measurements are given in Table 2. The tabulated values represent rounded results, obtained by calculation using the exact raw data. The test item gave a chromatographic profile consisting of several peaks, thereof two main peaks representing more than 75 % of the total test item area. Since the test item is a complex mixture of several constituents with different solubilities influencing each others, the measured water solubility has to be seen as an approximation. The number of peaks in the chromatograms increased with increasing stirring times and loading rate. It was not part of this study to determine whether these peaks are degradation products or impurities. These peaks were not used for the calculation of the water solubility.

The calibration solutions were verified by a second weighing and dilution into the calibration curve at levels of 2.66 and 24.5 mg/L. Analysis of these solutions gave recoveries of 101 % and 105 % compared to the nominal values.

The extraction method was tested under IES non-GLP study number 20170073. The method led to recoveries of 106 % and 101 % compared to the nominal values (0.109 mg test item /L).

Applicant's summary and conclusion

Conclusions:

During this study, the water solubility of VETYNAL was determined at 20 °C for two loading rates using OECD Guideline for the Testing of Chemicals, No. 105 adapted to a slow stirring design.

For a VETYNAL loading rate of 13 to 15 mg/L, the water solubility was found to be 0.598 ± 0.050 mg/L.

For a VETYNAL loading rate of 118 to 132 mg/L, the water solubility was found to be 0.981 ± 0.057 mg/L.

Since the test item is a complex mixture of several constituents with different solubilities influencing each others, the measured water solubility has to be seen as an approximation.

Executive summary:

During this study the water solubility of VETYNAL was determined based on the OECD Guideline for the Testing of Chemicals, No. 105: Water Solubility, modified to a slow-stirring test design.

VETYNAL is a complex mixture of several constituents. The test item gave a chromatographic profile consisting of several peaks, thereof two representing more than 75 % of the test item (area %). The calculations were based on the sum of these two peaks.

For a VETYNAL loading rate of 13 to 15 mg/L, the water solubility was found to be 0.598 ± 0.050 mg/L.

For a VETYNAL loading rate of 118 to 132 mg/L, the water solubility was found to be 0.981 ± 0.057 mg/L.

Since the test item is a mixture of several constituents with different solubilities, the results should be regarded as an approximated value.