D-Glucose, reaction products with alcohols C16-18 (even numbered)

Water solubility

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

water solubility

Type of information:

calculation (if not (Q)SAR)

Adequacy of study:

weight of evidence

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

accepted calculation method

Qualifier:

no guideline required

Principles of method if other than guideline:

- Software tool(s) used including version: ACD Perfecta, Release 14.0.0 (Build 2726, Nov 2014)

GLP compliance:

no

Type of method:

other: Calculation

Key result

Water solubility:

0.08 mg/L

Temp.:

25 °C

pH:

< 11.4

Remarks on result:

other: Calculated value for C16-alkyl monoglucoside

Key result

Water solubility:

0.008 mg/L

Temp.:

25 °C

pH:

< 11.4

Remarks on result:

other: Calculated value for C18-alkyl monoglucoside

Key result

Water solubility:

0.07 mg/L

Temp.:

25 °C

pH:

< 10.7

Remarks on result:

other: Calculated value for C16-alkyl diglucoside

Key result

Water solubility:

0.02 mg/L

Temp.:

25 °C

pH:

< 11.1

Remarks on result:

other: Calculated value for C18-alkyl diglucoside

Key result

Water solubility:

2.06 mg/L

Temp.:

25 °C

pH:

< 10.4

Remarks on result:

other: Calculated value for C16-alkyl triglucoside

Key result

Water solubility:

0.8 mg/L

Temp.:

25 °C

pH:

< 11.6

Remarks on result:

other: Calculated value for C18-alkyl triglucoside

Calculated solubilities

Constituent	CAS-No.	Calculated solubility @ 25 °C, [mg/L]	Value from literature
Glucose	50-99-7	385 g/L (pH < 9)	818 g/kg(15 °C)^[1]
Cetyl alcohol	36653-82-4	0.02	0.03 mg/kg^[2](25°C)
Stearyl alcohol	112-92-5	0.005	0.11 mg/kg^[2](34°C)
C16-alkyl monoglucoside	54549-27-8	0.08 (pH < 11,4)
C18-alkyl monoglucoside	27836-65-3	0.008 (pH < 11,4)
C16-alkyl diglucoside	-	0.07 (pH < 10,7)
C18-alkyl diglucoside	-	0.02 (pH < 11,1)
C16-alkyl triglucoside	-	2.06 (pH < 10,4)
C18-alkyl triglucoside	-	0.8 (pH <11,6)

[1] Stephen, H. and Stephen, T., Solubilities of organic and Inorganic Compounds, MacMillan, New York, 1963

[2] Solubility Data Series, International Union of Pure and Applied Chemistry, Vol. 15, Pergamon press, Oxford, 1982

Conclusions:

The calculated water solubilities of the alkyl glucosides constituents of the substance at 25 °C were found in the range from 0.008 mg/L (C18-alkyl monoglucoside) to 2.06 mg/L (C16-alkyl triglucoside).

Executive summary:

The substance is composed of a number of components including starting components. It is therefore not appropriate to determine the water solubility by experimental methods. Instead, the water solubility was determined for individual reaction products of D-glucose and C16/C18 alkylalcohols by using a calculation method provided by the software ACD PERCEPTA. The calculated water solubilities at 25 °C relating to the individual C16-alkyl and C18-alkyl glucosides are as follows:

C16-alkyl monoglucoside: 0.08 mg/L (pH < 11.4)

C18-alkyl monoglucoside: 0.008 mg/L (pH < 11.4)

C16-alkyl diglucoside: 0.07 mg/L (pH < 10.7)

C18-alkyl diglucoside: 0.02 mg/L (pH < 11.1)

C16-alkyl triglucoside: 2.06 mg/L (pH < 10.4)

C18-alkyl triglucoside: 0.8 mg/L (pH < 11.6)

Reference 2

Endpoint:

water solubility

Type of information:

calculation (if not (Q)SAR)

Adequacy of study:

weight of evidence

Study period:

2017-11-30

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

results derived from a valid (Q)SAR model and falling into its applicability domain, with adequate and reliable documentation / justification

Justification for type of information:

1. SOFTWARE
EPISUITE v4.11

2. MODEL (incl. version number) WSKOW v1.42

3. SMILES OR OTHER IDENTIFIERS USED AS INPUT FOR THE MODEL: see field "Specific details on test material used for the study"

4. SCIENTIFIC VALIDITY OF THE (Q)SAR MODEL
For detailed information about the used model please refer to the attached justification.

5. APPLICABILITY DOMAIN
For detailed information about the used model please refer to the attached justification.

6. ADEQUACY OF THE RESULT
For detailed information about the used model please refer to the attached justification.

Principles of method if other than guideline:

- Software tool(s) used including version: EPI Suite v4.1
- Model(s) used: WSKOW v1.42
- Model description: see field 'Attached justification'
- Justification of QSAR prediction: see field 'Attached justification'

GLP compliance:

no

Type of method:

other: computational

Specific details on test material used for the study:

SMILES code used for calculation:
Mono-C18-glucoside
C1(OCCCCCCCCCCCCCCCCCC)C(O)C(O)C(O)C(CO)O1

Mono-C16-glucoside
C1(OCCCCCCCCCCCCCCCC)C(O)C(O)C(O)C(CO)O1

Di-C18-glucoside
C(C(CO)OC(O)C1(O))(OC(C(CO)OC(OC(CCCCCCCCCCCCCCCCC))C2(O))C2O)C1O

Di-C16-glucoside
C(C(CO)OC(O)C1(O))(OC(C(CO)OC(OC(CCCCCCCCCCCCCCC))C2(O))C2O)C1O

Tri-C16-glucoside
C(C(CO)OC(OC(C(COC(C(COCCCCCCCCCCCCCCCC)OC(O)C1(O))C1O)OC(O)C2(O))C2O)C3(O))(O)C3O

Tri-C18-glucoside
C(C(CO)OC(OC(C(COC(C(COCCCCCCCCCCCCCCCC)OC(O)C1(O))C1O)OC(O)C2(O))C2O)C3(O))(O)C3O

Key result

Water solubility:

0.202 mg/L

Temp.:

25 °C

Remarks on result:

other: QSAR with C16-alkyl monoglucoside

Key result

Water solubility:

0.02 mg/L

Temp.:

25 °C

Remarks on result:

other: QSAR with C18-alkyl monoglucoside

Key result

Water solubility:

0.116 mg/L

Temp.:

25 °C

Remarks on result:

other: QSAR with C16-alkyl diglucoside

Key result

Water solubility:

0.011 mg/L

Temp.:

25 °C

Remarks on result:

other: QSAR with C18-alkyl diglucoside

Key result

Water solubility:

85.86 mg/L

Temp.:

25 °C

Remarks on result:

other: QSAR with C16-alkyl triglucoside

Key result

Water solubility:

8.076 mg/L

Temp.:

25 °C

Remarks on result:

other: QSAR with C18-alkyl triglucoside

Calculated water solubilities of individual constituents:

Constituent	CAS-No.	Calculated solubility, 25°C, [mg/L]	Value from literature
Glucose	50-99-7	1000 g/L	818 g/kg(15°C)^[1] 1200g/L (30°C)^[3]
Cetyl alcohol	36653-82-4	0.1495	0.03 mg/kg (25°C)^[2] 0.0411 mg/L (25°C)^[4]
Stearyl alcohol	112-92-5	0.0151	0.11 mg/kg(34°C)^[2] 0.0011 mg/L (25°C)^[5]
C16-alkyl monoglucoside	54549-27-8	0.2018
C18-alkyl monoglucoside	27836-65-3	0.01954
C16-alkyl diglucoside	-	0.1164
C18-alkyl diglucoside	-	0.01106
C16-alkyl triglucoside	-	85.86
C18-alkyl triglucoside	-	8.076

 

[1] Stephen, H. and Stephen, T., Solubilities of organic and Inorganic Compounds, MacMillan, New York, 1963

[2]Solubility Data Series, International Union of Pure and Applied Chemistry, Vol. 15, Pergamon press, Oxford, 1982

[3] Mullin, JW; Crystallisation, BOOKA, 425-426, 1972, CRC Press, Cleveland, OH

[4] Robb, ID; DETERMINATION OF THE AQUEOUS SOLUBILITY OF FATTY ACIDS AND ALCOHOLS.; AUST. J. CHEM.; 19:2281-4; 1966

[5] Yalkowsky, SH & Valvani, SC; SOLUBILITY AND PARTITIONING I: SOLUBILITY OF NONELECTROLYTES IN WATER.; J. PHARM.SCI.; 69:912-22.; 1980

 

Conclusions:

The calculated water solubilities of the alkyl glucosides constituents of the substance at 25 °C were found in the range from 0.01106 mg/l (C18-alkyl diglucoside) to 85.86 mg/l (C16-alkyl triglucoside).

Executive summary:

The substance is composed of a number of components including starting components. It is therefore not appropriate to determine the water solubility by experimental methods. Instead, the water solubility was determined for individual reaction products of D-glucose and C16/C18 alkylalcohols by using a calculation method provided by the software EPI suite 4.1, WSKOW v.1.42. The calculated water solubilities at 25 °C relating to the individual C16-alkyl and C18-alkyl glucosides are as follows:

C16-alkyl monoglucoside: 0.2018 mg/L

C18-alkyl monoglucoside: 0.01954 mg/L

C16-alkyl diglucoside: 0.1164 mg/L

C18-alkyl diglucoside: 0.01106 mg/L

C16-alkyl triglucoside: 85.86 mg/L

C18-alkyl triglucoside: 8.076 mg/L

Description of key information

The substance "Glucose, reaction products with alcohols C16-18" is composed of more than 6 individual chemical components indcluding starting material. The solubility of the components is quite different and were found in the range from 0.01106 mg/l (C18-alkyl diglucoside) to 85.86 mg/l (C16-alkyl triglucoside). According to basic physical-chemical knowledge, the solubility of each component is dependent of the amount of the concentration of each other component. Or, with other words, the solubility of each component is dependent on the loading rate of the total substance.

Therefore a total solubility for this mixture of substances can neither be defined nor measured.

Instead of a measurement, QSAR-calculations with two different calculation programs were made as well as a litereature search for some substances (starting materials).

Only for the calculation of exposure assessment, a value for water solubility is needed. Though there is no physically definable value for this mixture, for the two main components “ether of cetyl or stearyl alcohol with glucose” a value is calculated as follows:

C16-alkyl monoglucoside: mean of the results from WSKOW (0.2018 mg/l) and ACD Percepta (0.08 mg/l) = 0.1409 mg/l

C18-alkyl monoglucoside: mean of the results from WSKOW (0.01954 mg/l) and ACD Percepta (0.008 mg/l) = 0.01377 mg/l

Square root of the sum of quadratic results = 0.142 mg/l

Key value for chemical safety assessment

Water solubility:

0.142 mg/L

at the temperature of:

25 °C

Additional information

ACD PERCEPTA.

The calculated water solubilities at 25 °C relating to the individual C16-alkyl and C18-alkyl glucosides are as follows:

C16-alkyl monoglucoside: 0.08 mg/L (pH < 11.4)

C18-alkyl monoglucoside: 0.008 mg/L (pH < 11.4)

C16-alkyl diglucoside: 0.07 mg/L (pH < 10.7)

C18-alkyl diglucoside: 0.02 mg/L (pH < 11.1)

C16-alkyl triglucoside: 2.06 mg/L (pH < 10.4)

C18-alkyl triglucoside: 0.8 mg/L (pH < 11.6)

EPI suite 4.1, WSKOW v.1.42.

The calculated water solubilities at 25 °C relating to the individual C16-alkyl and C18-alkyl glucosides are as follows:

C16-alkyl monoglucoside: 0.2018 mg/L

C18-alkyl monoglucoside: 0.01954 mg/L

C16-alkyl diglucoside: 0.1164 mg/L

C18-alkyl diglucoside: 0.01106 mg/L

C16-alkyl triglucoside: 85.86 mg/L

C18-alkyl triglucoside: 8.076 mg/L