1,2,3-Propanetricarboxylic acid, 2-hydroxy-, tri-C12-13-branched alkyl esters

Bioaccumulation: aquatic / sediment

Administrative data

Endpoint:

bioaccumulation in aquatic species: fish

Type of information:

(Q)SAR

Adequacy of study:

key study

Study period:

2015

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Accepted calculation method on constituents

Justification for type of information:

QSAR prediction: migrated from IUCLID 5.6

Data source

Reference

Title:

No information

Year:

2015

Bibliographic source:

Reference: US EPA. Estimation Programs Interface Suite for Microsoft® Windows, v 4.10 or insert version used]. United States Environmental Protection Agency, Washington, DC, USA.

Materials and methods

Test guideline

Guideline:

other: REACh guidance on QSARs R6, May, July 2008

Principles of method if other than guideline:

General model for BCF. The BCFBAF program estimates BCF of an organic compound using the compound's log octanol-water partition coefficient (Kow).

Test material

Test material information

Constituent 1

Reference substance name:

tristridecyl 2-hydroxypropane-1,2,3-tricarboxylate

IUPAC Name:

tristridecyl 2-hydroxypropane-1,2,3-tricarboxylate

Constituent 2

Reference substance name:

trisdodecyl-2-hydroxypropane-1,2,3-tricarboxylate

IUPAC Name:

trisdodecyl-2-hydroxypropane-1,2,3-tricarboxylate

Constituent 3

Reference substance name:

CCCCCCCCCCC(C)COC(=O)CC(O)(C(=O)OCC(C)CCCCCCCCCC)CC(=O)OCC(C)CCCCCCCCCC

IUPAC Name:

CCCCCCCCCCC(C)COC(=O)CC(O)(C(=O)OCC(C)CCCCCCCCCC)CC(=O)OCC(C)CCCCCCCCCC

Constituent 4

Reference substance name:

CCCCCCCCCC(C)COC(=O)CC(O)(C(=O)OCC(C)CCCCCCCCC)CC(=O)OCC(C)CCCCCCCCC

IUPAC Name:

CCCCCCCCCC(C)COC(=O)CC(O)(C(=O)OCC(C)CCCCCCCCC)CC(=O)OCC(C)CCCCCCCCC

Constituent 5

Reference substance name:

CCCCCC(CCCCC)COC(=O)CC(O)(C(=O)OCC(CCCCC)CCCCC)CC(=O)OCC(CCCCC)CCCCC

IUPAC Name:

CCCCCC(CCCCC)COC(=O)CC(O)(C(=O)OCC(CCCCC)CCCCC)CC(=O)OCC(CCCCC)CCCCC

Test material form:

other: not specified

Test organisms

Test organisms (species):

other: Model based on fish data

Test conditions

Details on estimation of bioconcentration:

BASIS FOR CALCULATION OF BCF

The BCFBAF version 3.01 programme of the EPI Suite software (EPISuite (v4.11) was used to predict the BCF either regression-based estimate or Arnot-Gobas upper trophic estimate.

INSERTION PARAMETERS FOR MODEL
Tristridecyl 2-hydroxypropane-1,2,3-tricarboxylate, tridecyl with the following branching alcohol part 2-methydodecyl:
- SMILES : CCCCCCCCCCC(C)COC(=O)CC(O)(C(=O)OCC(C)CCCCCCCCCC)CC(=O)OCC(C)CCCCCCCCCC
- Molecular formular: C45 H86 O7
- Molecular weight : 739.18
- Result based on calculated log Pow of: 16.32

Log BCF from regression-based method = 0.500 (BCF = 3.162 L/kg wet-wt)
Log BCF Arnot-Gobas method (upper trophic) = -0.049 (BCF = 0.893)
Log BAF Arnot-Gobas method (upper trophic) = -0.049 (BAF = 0.893)

and:
Tristridecyl 2-hydroxypropane-1,2,3-tricarboxylate, tridecyl with the following branched alcohol part 2-pentyloctyl:
- Smiles: CCCCCCC(CCCCC)COC(=O)CC(O)(C(=O)OCC(CCCCC)CCCCCC)CC(=O)OCC(CCCCC)CCCCCC
- Molecular formular: C45 H86 O7
- Molecular weight : 739.18
- Result based on calculated log Pow of: 16.32

Log BCF from regression-based method = 0.500 (BCF = 3.162 L/kg wet-wt)
Log BCF Arnot-Gobas method (upper trophic) = -0.049 (BCF = 0.893)
Log BAF Arnot-Gobas method (upper trophic) = -0.049 (BAF = 0.893)

and:
Trisdodecyl 2-hydroxypropane-1,2,3-tricarboxylate, tridecyl with the following branching alcohol part 2-methyundecyl:
- Smiles: CCCCCCCCCC(C)COC(=O)CC(O)(C(=O)OCC(C)CCCCCCCCC)CC(=O)OCC(C)CCCCCCCCC
- Molecular formular: C42 H80 O7
- Molecular weight : 697.10
- Result based on calculated log Pow of: 14.85

Log BCF from regression-based method = 0.500 (BCF = 3.162 L/kg wet-wt)
Log BCF Arnot-Gobas method (upper trophic) = -0.049 (BCF = 0.893)
Log BAF Arnot-Gobas method (upper trophic) = -0.049 (BAF = 0.893)

and:
Trisdodecyl 2-hydroxypropane-1,2,3-tricarboxylate, tridecyl with the following branched alcohol part 2-pentylheptanyl:
- Smiles: CCCCCC(CCCCC)COC(=O)CC(O)(C(=O)OCC(CCCCC)CCCCC)CC(=O)OCC(CCCCC)CCCCC
- Molecular formular: C42 H80 O7
- Molecular weight : 697.10
- Result based on calculated log Pow of: 14.85

Log BCF from regression-based method = 0.500 (BCF = 3.162 L/kg wet-wt)
Log BCF Arnot-Gobas method (upper trophic) = -0.049 (BCF = 0.893)
Log BAF Arnot-Gobas method (upper trophic) = -0.049 (BAF = 0.893)

Results and discussion

Bioaccumulation factor

Bioaccumulation factor 1

Key result

Type:

BCF

Value:

3.162 L/kg

Basis:

whole body w.w.

Calculation basis:

other: calculation

Remarks on result:

other: regression-based estimate

Bioaccumulation factor 2

Key result

Type:

BAF

Value:

0.893 L/kg

Basis:

whole body w.w.

Calculation basis:

other: calculation

Remarks on result:

other: Arnot-Gobas upper trophic

Details on kinetic parameters:

Biotransformation Rate Constant:
kM (Rate Constant): 0.116 /day (10 gram fish)
kM (Rate Constant): 0.06522 /day (100 gram fish)
kM (Rate Constant): 0.03668 /day (1 kg fish)
kM (Rate Constant): 0.02062 /day (10 kg fish)

Metabolites:

===========================================================
Whole Body Primary Biotransformation Rate Estimate for Fish:
===========================================================
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | LOG BIOTRANSFORMATION FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 3 | Linear C4 terminal chain [CCC-CH3] | 0.0341 | 0.1024
Frag | 3 | Ester [-C(=O)-O-C] | -0.7605 | -2.2816
Frag | 1 | Carbon with 4 single bonds & no hydrogens | -0.2984 | -0.2984
Frag | 6 | Methyl [-CH3] | 0.2451 | 1.4706
Frag | 32 | -CH2- [linear] | 0.0242 | 0.7740
Frag | 3 | -CH- [linear] | -0.1912 | -0.5737
L Kow| * | Log Kow = 16.32 (KowWin estimate) | 0.3073 | 5.0157
MolWt| * | Molecular Weight Parameter | | -1.8955
Const| * | Equation Constant | | -1.5371
============+============================================+=========+=========
RESULT | LOG Bio Half-Life (days) | | 0.7764

Details on results:

The BCFBAF version 3.01 programme of the EPI Suite software (EPISuite 4.10) was used to predict either a log BCF of 0.5 (BCF of 3.16 L/kg) based on a regression estimate or a log BAF of - 0.05 (BAF of 0.893 L/kg) based on the Arnot-Gobas upper trophic model both using the smiles codes of tristirdedecyl 2-hydroxypropane-1,2,3-tricarboxylate and trisdodecyl 2-hydroxypropane-1,2,3-tricarboxylate representing Cosmacol ECI.

Based on the expected kinetic behaviour in the body substantial amounts of Cosmacol ECI will not accumulate in the body, because it will be hydrolysed, absorbed and efficiently metabolised into water soluble metabolites, which is supported by the molecular structure of Cosmcaol ECI and its physico-chemical properties.

Arnot-Gobas BCF & BAF Methods (including biotransformation rate estimates):
Estimated Log BCF (upper trophic) = -0.049 (BCF = 0.893 L/kg wet-wt)
Estimated Log BAF (upper trophic) = -0.049 (BAF = 0.893 L/kg wet-wt)
Estimated Log BCF (mid trophic) = -0.031 (BCF = 0.9315 L/kg wet-wt)
Estimated Log BAF (mid trophic) = -0.031 (BAF = 0.9316 L/kg wet-wt)
Estimated Log BCF (lower trophic) = -0.027 (BCF = 0.9402 L/kg wet-wt)
Estimated Log BAF (lower trophic) = -0.027 (BAF = 0.9404 L/kg wet-wt)

Arnot-Gobas BCF & BAF Methods (assuming a biotransformation rate of zero):
Estimated Log BCF (upper trophic) = -0.049 (BCF = 0.893 L/kg wet-wt)
Estimated Log BAF (upper trophic) = 0.041 (BAF = 1.1 L/kg wet-wt)


RESULT | LOG Bio Half-Life (days) | | 0.7764
RESULT | Bio Half-Life (days) | | 5.976
NOTE | Bio Half-Life Normalized to 10 g fish at 15 deg C |

Log BCF (regression-based estimate): 0.50 (BCF = 3.16 L/kg wet-wt)
Biotransformation Half-Life (days) : 5.98 (normalized to 10 g fish)
Log BAF (Arnot-Gobas upper trophic): -0.05 (BAF = 0.893 L/kg wet-wt)

Reported statistics:

The BCFBAF model had the following statistics:
Training Set
number = 527
correlation coef (r2) = 0.833
Validation Set
number = 158
correlation coef (r2) = 0.82

Any other information on results incl. tables

Summary Results:

Log BCF (regression-based estimate): 0.50 (BCF = 3.16 L/kg wet-wt)

Biotransformation Half-Life (days) : 5.98 (normalized to 10 g fish)

Log BAF (Arnot-Gobas upper trophic): -0.05 (BAF = 0.893 L/kg wet-wt)

Log Kow used by BCF estimates: 16.32

Equation Used to Make BCF estimate: Log BCF = -0.49 log Kow + 7.554 + Correction Correction(s): Value No Applicable Correction Factors Minimum Log BCF of 0.50 applied when Log Kow > 7

Estimated Log BCF = 0.500 (BCF = 3.162 L/kg wet-wt)

Applicant's summary and conclusion

Conclusions:

It is concluded that Cosmacol ECI will not accumulate in the body.

Executive summary:

The BCFBAF version 3.01 programme of the EPI Suite software (v 4.10) was used to predict either a log BCF of 0.5 (BCF of 3.16 L/kg) based on a regression estimate or a log BAF of - 0.05 (BAF of 0.893 L/kg) based on the Arnot-Gobas upper trophic model both using the smiles codes of tristridecyl 2 -hydroxypropane-1,2,3 -tricarboxylate and tridodecyl 2 -hydroxypropane-1,2,3 -tricarboxylate representing Cosmacol ECI . Because the Arnot-Gobas upper trophic model takes also into account metabolism of the substance by the organism it is lower. The QSAR-data are supported by the results of the pharmacokinetics. Cosmacol ECI will be hydrolysed, absorbed and efficiently metabolised into water soluble metabolites, which is supported by the molecular structure of Cosmacol ECI and its physico-chemical properties.

It is concluded that Cosmacol ECI will not accumulate in the body.