Reaction mass of (3R)-3-[(1R)-4-methyl-3-cyclohexen-1-yl]butanal and (3S)-3-[(1R)-4-methyl-3-cyclohexen-1-yl]butanal

Water solubility

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

water solubility

Remarks:

Critical Micelle Concentration

Type of information:

experimental study

Adequacy of study:

key study

Study period:

07 December - 01 December 2016

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

comparable to guideline study

Remarks:

Non guideline study based on or adapted from: ISO 4311: Anionic and non-ionic surface active agents – Determination of the critical micelle concentration – Method by measuring surface tension with a plate, stirrup or ring. Test conducted in accordance with GLP.

Qualifier:

according to guideline

Guideline:

other: Based on or adapted from: ISO 4311: Anionic and non-ionic surface active agents – Determination of the critical micelle concentration – Method by measuring surface tension with a plate, stirrup or ring.

Deviations:

no

Principles of method if other than guideline:

The critical micelle concentration (CMC) was determined by measuring the surface tension of test item solutions at different test item concentrations. For surface active substances which form micelles in solution, the surface tension decreases with increasing concentration until the CMC is reached. At concentrations above the CMC, the surface tension remains constant.

GLP compliance:

yes (incl. QA statement)

Type of method:

other: Surface tension measured using OECD harmonised ring method

Specific details on test material used for the study:

STABILITY AND STORAGE CONDITIONS OF TEST MATERIAL
- Storage condition of test material: Room temperature
- Stability under test conditions: Assumed stable. Stability at higher temperatures not availbale.
- Solubility and stability of the test substance in the solvent/vehicle: N/A
- Reactivity of the test substance with the solvent/vehicle of the cell culture medium: N/A

Remarks on result:

other: The endpoint is critical micelle concentration, see "details on results"

Details on results:

The response of surface tension of the test solutions as function of increasing concentration shows no transition phase or stationary phase up to the limit of observed solubility. It is therefore concluded that the test item has no critical micelle concentration.

The results of the test on the determination of the surface tension of the test solution are given in Table 2 through Table 4.

 Table 2       Surface Tension for Test Solution at 1 mg/L

Measurement	Time passed after transfer test solution to test vessel [minutes]	Surface tension [mN/m]
		individual	mean	mean multiplied by Φband Harkins-Jordan corrected value
1	15	75.2	74.7^1	74.7
2	16	74.5
3	17	74.9
4	18	74.7
5	19	74.8
6	20	74.7

¹mean calculated from measurements 2 to 6, after equlibrium was reached

Table 3       Surface Tension for Test Solution at 10 mg/L

Measurement	Time passed after transfer test solution to test vessel [minutes]	Surface tension [mN/m]
		individual	mean	mean multiplied by Φband Harkins-Jordan corrected value
1	16	74.6	74.3^1	74.3
2	17	74.3
3	18	75.0
4	19	75.4
5	20	74.4
6	21	74.3
7	22	74.2
8	23	74.4
9	24	74.4

¹mean calculated from measurements 5 to 9, after equlibrium was reached

Table 4       Surface Tension for Test Solution at 50 mg/L

Measurement	Time passed after transfer test solution to test vessel [minutes]	Surface tension [mN/m]
		individual	mean	mean multiplied by Φband Harkins-Jordan corrected value
1	21	71.4	70.1^1	70.0
2	22	70.9
3	23	70.0
4	24	70.1
5	25	70.4
6	26	70.0
7	27	70.1

¹mean calculated from measurements 3 to 7, after equlibrium was reached

 

Conclusions:

The response of surface tension of the test solutions as function of increasing concentration shows no transition phase or stationary phase up to the limit of observed solubility. It is therefore concluded that the test item has no critical micelle concentration.

Executive summary:

The critical micelle concentration of the test item was determined by measuring the surface tension of test item solutions at different test item concentrations in accordance with EU Method A.5. Critical micelle concentration for reaction mass of (3R)-3-[(1R)-4-Methyl-3-cyclohexen-1-yl]butanal and (3S)-3-[(1R)-4-Methyl-3-cyclohexen-1-yl]butanal could not be determined, hence it can be concluded that the test item has no critical micelle concentration.

Reference 2

Endpoint:

water solubility

Type of information:

experimental study

Adequacy of study:

key study

Study period:

21 October - 30 November 2016

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Remarks:

The study was conducted in accordance with international guidelines and in accordance with GLP. All relevant validity criteria were met.

Qualifier:

according to guideline

Guideline:

OECD Guideline 105 (Water Solubility)

Deviations:

no

Qualifier:

according to guideline

Guideline:

EU Method A.6 (Water Solubility)

Deviations:

no

Qualifier:

according to guideline

Guideline:

EPA OPPTS 830.7840 (Water Solubility)

Deviations:

no

GLP compliance:

yes (incl. QA statement)

Type of method:

flask method

Specific details on test material used for the study:

STABILITY AND STORAGE CONDITIONS OF TEST MATERIAL
- Storage condition of test material: Room temperature
- Stability under test conditions: Assumed stable. Stability at higher temperatures not availbale.
- Solubility and stability of the test substance in the solvent/vehicle: N/A
- Reactivity of the test substance with the solvent/vehicle of the cell culture medium: N/A

Key result

Water solubility:

0.266 g/L

Conc. based on:

test mat. (dissolved fraction)

Incubation duration:

96 h

Temp.:

20 °C

pH:

>= 6.6 - <= 7.5

Prelim test

The content of the test item dissolved in the water sample was 0.0850 g/L.

Main Test

The results of anaysis from 24, 48, 72 and 96 h sampling are shown in Table 1.

The maximum difference (MD) of the concentrations determined in the 24, 48, 72 and 96 hour test samples was>15%. Based on this, the water solubility of the test item is given as the mean value of the 72- and 96-hour measurements.

Table 1       Water Solubility of the Test Item

Stirring Time (h)	Analysed Concentration (g/L)	Mean^1 (g/L)	MD (%)	pH
24	0.196			6.6
48	0.190			6.6
72	0.254			6.6
96	0.279	0.266	9.4	7.5

¹mean value of the 72 and 96 h measurements

No test item was detected in the blank water sample.

 

Conclusions:

The slow-stirring flask method was applied for the determination of the water solubility of Reaction mass of (3R)-3-[(1R)-4-Methyl-3-cyclohexen-1-yl]butanal and (3S)-3-[(1R)-4-Methyl-3-cyclohexen-1-yl]butanal.

The water solubility of the test item at 20 °C was 0.266 g/L. The pH of the aqueous samples was 6.6 – 7.5.

Executive summary:

The water solubility of the test substance was determined in accordance with EU Method A.6 using the slow stir method- appropriate for test substances with a water solubility below 0.2 mg/L.

The water solubility of the test substance at 20°C was 0.266 g/L. The pH of the aqueous samples was 6.6 - 7.5.

 

Description of key information

Water Solublity.: 0.266 g/L at 20 ºC, EU Method A.6, Anon, 2017.

Critical Micelle Concentration: No critical micelle concentration, ISO 4311 Anionic and non-ionic surface active agents- Determination of the critical micelle concentration- Method by measuring surface tension with a plate, stirrup or ring., Anon, 2017.

Key value for chemical safety assessment

Water solubility:

0.266 g/L

at the temperature of:

20 °C

Additional information

Attempts to determine the critical micelle concentration of the test substance were made by measuring the surface tension of test item solutions at increasing test item concentrations in accordance with EU Method A.5. Critical micelle concentration for reaction mass of (3R)-3-[(1R)-4-Methyl-3-cyclohexen-1-yl]butanal and (3S)-3-[(1R)-4-Methyl-3-cyclohexen-1-yl]butanal could not be determined at the limit of observed solubility. It can be concluded that the test item has no critical micelle concentration.

 

The critical micelle concentration assay was conducted in response to the surface tension measurement as a surrogate for water solubility, the surface tension measurement of 57.9 mN/m indicated that the substance was borderline surface-active. As no critical micelle concentration could be determined, it was concluded that the substance does not behave like a surfactant, and the low surface tension measurement was potentially an artefact of surface active impurities (trace carboxylic acid or an alkoxy- equivalent) with a higher water solubility than the test item, causing a false positive in the OECD 115 surface tension measurement at 90 % saturation.

 

The surface tension measurement of < 60 mN/m was therefore not considered to preclude the use of EU Method A.6. for water solubility.

 

The water solubility of the test substance was determined in accordance with EU Method A.6 using the slow stir method- appropriate for test substances with a water solubility below 0.2 mg/L.

 

The water solubility of the test substance at 20°C was 0.266 g/L. The pH of the aqueous samples was 6.6 - 7.5.