(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid

Water solubility

Administrative data

Endpoint:

water solubility

Type of information:

experimental study

Adequacy of study:

key study

Study period:

Dec. 2013 - Feb. 2014

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

other: Fully documented study according to international guidelines and under GLP guidelines.

Data source

Reference

Reference Type:

study report

Title:

Unnamed

Year:

2014

Report date:

2014

Materials and methods

Test guideline

Test guideline 1

Qualifier:

according to guideline

Guideline:

OECD Guideline 105 (Water Solubility)

Deviations:

yes

Remarks:

The concentrations of at least the last 2 vessels do not differ by more than 15%. The concentrations are alternatively increasing and decreasing. This discrepancy is presumably mainly caused by the application of large dilution factors

Test guideline 2

Qualifier:

according to guideline

Guideline:

EU Method A.6 (Water Solubility)

Deviations:

yes

Remarks:

The concentrations of at least the last 2 vessels do not differ by more than 15%. The concentrations are alternatively increasing and decreasing. This discrepancy is presumably mainly caused by the application of large dilution factors

Principles of method if other than guideline:

Although, the concentrations of at least the last 2 vessels differ by more than 15%, it was decided to use all 6 determinations for the calculation of the water solubility. The concentrations are alternatively increasing and decreasing. This discrepancy is presumably mainly caused by the application of large dilution factors for the chemical analysis. Since the whole test did not show a tendency of increasing values, the results are acceptable.

GLP compliance:

yes (incl. QA statement)

Type of method:

flask method

Test material

Test material information

Constituent 1

Reference substance name:

(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid

EC Number:

205-334-2

EC Name:

(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid

Cas Number:

138-59-0

Molecular formula:

C7H10O5

IUPAC Name:

(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid

Test material form:

solid: crystalline

Details on test material:

Sample from Batch no. 1329R037, Lot no. 0700791872

Results and discussion

Water solubility

Water solubility:

ca. 267 g/L

Temp.:

29.6 °C

pH:

> 2 - < 2.2

Remarks on result:

other: The last 24 h of the test were at 20.0 ± 0.5°C.

Any other information on results incl. tables

The measured concentrations were as follows:

254 g/l after 48 h (i.e. 24 h at 29.6 ± 0.2°C and 24 h at 20.0 ± 0.5°C), pH 2.1
278 g/l after 72 h (i.e. 48 h at 29.6 ± 0.2°C and 24 h at 20.0 ± 0.5°C), pH 2.2
274 g/l after 96 h (i.e. 72 h at 29.6 ± 0.2°C and 24 h at 20.0 ± 0.5°C) pH 2.0
238 g/l after 172 h (i.e. 144 h at 29.6 ± 0.2°C and 24 h at 20.0 ± 0.5°C) pH 2.1
249 g/l after 192 h (i.e. 168 h at 29.6 ± 0.2°C and 24 h at 20.0 ± 0.5°C) pH 2.2
306 g/l after 216 h (i.e. 192 h at 29.6 ± 0.2°C and 24 h at 20.0 ± 0.5°C) pH 2.1

The water solubility of (-)-Shikimic acid, calculated as the mean value of all six determinations, is 267 g/l.

Although, the concentrations of at least the last 2 vessels differ by more than 15%, it was decided to use all 6 determinations for the calculation of the water solubility. The concentrations are alternatively increasing and decreasing. This discrepancy is presumably mainly caused by the application of large dilution factors for the chemical analysis. Since the whole test did not show a tendency of increasing values, the results are acceptable.

Applicant's summary and conclusion

Conclusions:

Interpretation of results (migrated information): very soluble (> 10000 mg/L)
The water solubility of (-)-Shikimic acid, calculated as the mean value of all six determinations, is 267 g/l.

Executive summary:

The water solubility of (-)-Shikimic acid was determined with the flask method according to OECD 105 and EU method A6.

The water solubility of (-)-Shikimic acidwas investigated by dissolving the test substance in tightly sealed test vessels at 30°C for at least 24 h and equilibration at 20°C for another 24 h, both by using a magnetic stirrer.

The initially added amount of test substance was 500 g per litre deionised water. All samples were filtrated before chemical analysis by HPLC using MILLIPORE AP15 glass fibre filters.

The water solubility of (-)-Shikimic acid, calculated as the mean value of all six determinations, is 267 g/l.

Although, the concentrations of at least the last 2 vessels differ by more than 15%, it was decided to use all 6 determinations for the calculation of the water solubility. The concentrations are alternatively increasing and decreasing. This discrepancy is presumably mainly caused by the application of large dilution factors for the chemical analysis. Since the whole test did not show a tendency of increasing values, the results are acceptable.