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Partition coefficient

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Endpoint:
partition coefficient
Type of information:
experimental study
Adequacy of study:
key study
Study period:
Jan 2012-Sept 2012
Reliability:
1 (reliable without restriction)
Rationale for reliability incl. deficiencies:
guideline study
Qualifier:
according to guideline
Guideline:
OECD Guideline 107 (Partition Coefficient (n-octanol / water), Shake Flask Method)
Deviations:
no
GLP compliance:
yes
Type of method:
other: OSA is a surface-active material and OECD Guideline 107 states that, for a surface-active material, Kow is determined by dividing the n-octanol solubility value by the water solubility value.
Partition coefficient type:
octanol-water
Analytical method:
other: electron impact gas chromatorgraphy/mass spectrophotometry (EI-GC/MS)
Type:
Pow
Partition coefficient:
>= 48 328.1
Temp.:
22 °C
pH:
7
Type:
log Pow
Partition coefficient:
>= 4.68
Temp.:
22 °C
pH:
7
Details on results:
A clear solution was observed at a test concentration of 20 mg/L of OSA in pH 7 buffer, indicating that the solubility of OSA is approximately 20 mg/L. This was further confirmed by EI-GC/MS analysis, where the recovery of the test substance was determined to be 10.44 mg/L or 52.2%, w/v with the low recovery rate due to partial hydrolysis.
A visual observation of the solubility of OSA in n-octanol indicated that OSA seemed to be completely soluble regardless of the ratio of OSA in n-octanol. This was further confirmed by EI-GC/MS analysis, where the recovery of the test solution was determined to be 101% at a concentration of 50% in n-octanol (w/v). It was also confirmed that no degradation was observed while the sample was setting for 10 minutes prior to further dilutions.
Buffer quality control samples resulted in measurements ranging from 95.5 to 97.1% (N = 2) during testing. The results of the n-octanol quality control samples resulted in measurements ranging from 109 to 117% (N = 2). Based on these results, it was established that the appropriate quality control was maintained during the analyses.
 

The partition coefficient (Kow) was estimated based on the EI-GC/MS analysis of the solubility of the test substance in the pure solvents to be ≥ 48328.1 and log Kow to be ≥ 4.68.

(The partition coefficient (Kow) was also estimated based on the EI-GC/MS analysis of the solubility of the test substance inn-octanol and visual estimate of solubility in pH 7 buffer to be ≥ 25238.9 and log Kow to be ≥ 4.40.)

Visual observation of OSA in pH 7 buffer solution

Concentration (mg/L)

Visual Observations

 

0 minutes

3 minutes

5

-

-

10

-

-

20

-

-

30

+

+

Note: “-” = clear (transparent).

“+” = cloudy (hazy, immiscible microdroplets).

 

Partition coefficient (Kow) determination of OSA in n-octanol and pH 7 buffer by EI-GC/MS

Matrix

Sample ID

Retention Time (min)

Analyzed Concentration (mg/L)

Kow

Log Kow

n-Octanol

OSA –Octanol, 1 minute

6.996

504778.7

48328.1 (25238.9)d

4.68 (4.40)d

OSA –Octanol, 10 minutes

6.998

555129.9

53148.8 (27756.5)d

4.73(4.44)d

pH 7 buffer

OSA _ Sa, 20 mg/L

Nab

10.4 (52.2%)c

NA

a S = Solubility.

b NA = Not Applicable.

c The percent low recovery rate by EI-GC/MS may be attributed to partial hydrolysis.

d Value was calculated based on the ratio of analyzed concentration inn-octanol/visual solubility without hydrolysis.

Note: The values presented in this table were calculated based on unrounded experimental results.

 

 

 

Conclusions:
The partition coefficient (Kow) for octenyl succinic anhyride was estimated based on the solubilities of the material in n-octanol and in aqueous buffer pH 7 at 22 degrees C. Solubility in water was determined by visual observation and by quantitation by EI-GC/MS analysis. The partition coefficient was ≥ 48328.1, and log Kow was ≥ 4.68 based on levels determined by analytic quantitation. The partition coefficient (Kow) was also estimated based on the analytically determined values of the solubility of the test substance in n-octanol and visual estimate of solubility in pH 7 buffer. This less precise value was ≥ 25238.9, and log Kow was ≥ 4.40.
Endpoint:
partition coefficient
Type of information:
(Q)SAR
Adequacy of study:
supporting study
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: Validated QSAR model from U.S. EPA EPI Suite.
Justification for type of information:
QSAR prediction: migrated from IUCLID 5.6
Principles of method if other than guideline:
Validated QSAR model contained in U.S. EPA EPI Suite.
GLP compliance:
no
Type of method:
other: QSAR model
Partition coefficient type:
octanol-water
Type:
log Pow
Partition coefficient:
3.42
Remarks on result:
other: QSAR prediction, not conducted at controlled temperature or pH condition.
Details on results:
Log Kow(version 1.68 estimate): 3.42

SMILES : O=C(CCC(=O)OCCCCCCC=C)O
CHEM : Octenyl succinate
MOL FOR: C12 H20 O4
MOL WT : 228.29
-------+-----+--------------------------------------------+---------+--------
TYPE | NUM | LOGKOW FRAGMENT DESCRIPTION | COEFF | VALUE
-------+-----+--------------------------------------------+---------+--------
Frag | 8 | -CH2- [aliphatic carbon] | 0.4911 | 3.9288
Frag | 1 | =CH2 [olefinic carbon] | 0.5184 | 0.5184
Frag | 1 | =CH- or =C< [olefinc carbon] | 0.3836 | 0.3836
Frag | 1 | -COOH [acid, aliphatic attach] |-0.6895 | -0.6895
Frag | 1 | -C(=O)O [ester, aliphatic attach] |-0.9505 | -0.9505
Const | | Equation Constant | | 0.2290
-------+-----+--------------------------------------------+---------+--------
Log Kow = 3.4198

------------------------------------------------------------------------------
Conclusions:
The octanol-water partition coefficient of octenyl succinate (the hydrolysis product of octenyl succinic anhydride) was estimated by QSAR to be log Kow = 3.42. Data can be read-across among members of the C8-12 Alkenyl Succinic Anhydrides Category, based on common functional groups, similar break-down products and potency patterns among carbon-chain length. This is adequate to fulfill the information requirements, to be the basis for classification and labelling decisions, and for risk assessment.

Description of key information

The log Kow is ≥ 4.68. 

Key value for chemical safety assessment

Log Kow (Log Pow):
4.68
at the temperature of:
22 °C

Additional information

The n-octanol:water partition coefficient of Tetrapropenyl succinic anhydride (TPSA) was experimentally determined according to an OECD 107 protocol for surface-active substances. The solubilities of the substance in n-octanol and in pH 7 aqueous buffer were individually determined by EI-GC/MS analysis and the ratio (n:octanol to buffer) was calculated. The Kow was estimated to be ≥ 48328.1 and the log Kow to be ≥ 4.68.