Reaction mass of: N,N'-[1,3-Phenylenebis(methylene)bis[12-hydroxyoctadecanamide], N,N'-hexane-1,6-diylbis(12-hydroxyoctadecanamide) and N,N'-ethane-1,2-diylbis(12-hydroxyoctadecan-1-amide)

Toxicity to aquatic algae and cyanobacteria

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

toxicity to aquatic algae and cyanobacteria

Type of information:

experimental study

Adequacy of study:

key study

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Qualifier:

according to guideline

Guideline:

EU Method C.3 (Algal Inhibition test)

Version / remarks:

EEC Directive 92/69, C.3

GLP compliance:

yes

Specific details on test material used for the study:

- Name of test material (as cited in study report): Amide #71

Details on test solutions:

Identity and concentration of auxiliary solvent for dispersal: none

Test organisms (species):

Raphidocelis subcapitata (previous names: Pseudokirchneriella subcapitata, Selenastrum capricornutum)

Limit test:

no

Total exposure duration:

72 h

Hardness:

24 mg CaCO3/L

Duration:

72 h

Dose descriptor:

EC50

Effect conc.:

ca. 71 mg/L

Conc. based on:

test mat.

Basis for effect:

biomass

Duration:

72 h

Dose descriptor:

EC50

Effect conc.:

ca. 71 mg/L

Conc. based on:

test mat.

Basis for effect:

growth rate

Duration:

72 h

Dose descriptor:

NOEC

Effect conc.:

10 mg/L

Conc. based on:

test mat.

Basis for effect:

biomass

Duration:

72 h

Dose descriptor:

NOEC

Effect conc.:

10 mg/L

Conc. based on:

test mat.

Basis for effect:

growth rate

Details on results:

%Concentration loss over test: 65 ... 27

Validity criteria fulfilled:

not specified

Conclusions:

The EC50 (72 h) of 1,3-bis[12-hydroxy-octadecamide-N-methylene]-benzene for Pseudokirchneriella subcapitata is 71 mg/L. The respective NOEC is 10 mg/L.

Executive summary:

The toxicity for aquatic algae of 1,3-bis[12-hydroxy-octadecamide-N-methylene]-benzene is assessed in a guideline study according to EU Method C.3 using Pseudokirchneriella subcapitata. The EC50 (72 h) is 71 mg/L, which is beyond water solubility of the substance (< 0.64 mg/L). The respective NOEC is 10 mg/L.

Reference 2

Endpoint:

toxicity to aquatic algae and cyanobacteria

Type of information:

experimental study

Adequacy of study:

key study

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Qualifier:

according to guideline

Guideline:

EU Method C.3 (Algal Inhibition test)

Version / remarks:

92/69/EEC, C3 (OECD Guideline No 201)

GLP compliance:

yes

Details on test solutions:

Identity and concentration of auxiliary solvent for dispersal: Sterile nutrient medium.

Test organisms (species):

Selenastrum sp.

Details on test organisms:

Test organism: Selenastrum capricornutum, Strain No. CCAP 278/4
A saturated solution was prepared by stirring test medium containing 100 mg/L (nominal) of test substance for 24 hours. The solution was filtered through filter paper to remove particulate matter.
The test substance could not be analysed since the analytical limit of quantitation (5 µg/L) exceeded the test substance solubility limit.

Water media type:

freshwater

Limit test:

no

Total exposure duration:

72 h

Duration:

72 h

Dose descriptor:

EC50

Conc. based on:

test mat.

Basis for effect:

biomass

Remarks on result:

not determinable because of methodological limitations

Remarks:

The 72 h EbC50 is greater than the limit of solubility.

Duration:

72 h

Dose descriptor:

EC50

Conc. based on:

test mat.

Basis for effect:

growth rate

Remarks on result:

not determinable because of methodological limitations

Remarks:

The 72 h ErC50 is greater than the limit of solubility.

Duration:

72 h

Dose descriptor:

NOEC

Effect conc.:

< 0.5 µg/L

Conc. based on:

test mat.

Basis for effect:

not specified

Remarks on result:

not determinable because of methodological limitations

Remarks:

The observed inhibition was shown to be statistically significant and therefore the 72 h NOEC should be taken as less than the analytical limit of detection (0.5 µg/l).

Validity criteria fulfilled:

not specified

Conclusions:

The EC50 (72 h) of 12-hydroxyoctadecanoic acid, reaction products with 1,3-benzenedimethanamine and hexamethylenediamine for Selenastrum capricornutum is greater than the limit of solubility. The respective NOEC is less than the limit of detection (< 0.5 µg/L).

Executive summary:

The toxicity for aquatic algae of 12-hydroxyoctadecanoic acid, reaction products with 1,3-benzenedimethanamine and hexamethylenediamine is assessed in a guideline study according to EU Method C.3 using Selenastrum capricornutum. The EC50 (72 h) is greater than the limit of solubility. The respective NOEC is less than the limit of detection (< 0.5 µg/L).

Reference 3

Endpoint:

toxicity to aquatic algae and cyanobacteria

Data waiving:

study scientifically not necessary / other information available

Justification for data waiving:

other:

Reference 4

Endpoint:

toxicity to aquatic algae and cyanobacteria

Type of information:

(Q)SAR

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

accepted calculation method

Justification for type of information:

The toxicity to aquatic algae is estimated based on EPI Suite, ECOSAR v1.11. Two models are available, the estimation from the class (Amides) and the Baseline Toxicity (neutral organic structure activity relationship).

Principles of method if other than guideline:

The toxicity to aquatic algae is estimated based on EPI Suite, ECOSAR v1.11. Two models are available, the estimation from the class (Amides) and the Baseline Toxicity (neutral organic structure activity relationship).

GLP compliance:

no

Specific details on test material used for the study:

Calculation is based on the structure of the test material.
- Name of test material (as cited in study report): Octadecanamide, N,N -1,2-ethanediylbis[12-hydroxy-

Analytical monitoring:

not required

Vehicle:

not specified

Test organisms (species):

other: Green algae, calculated

Test type:

other: estimation by calculation

Water media type:

not specified

Duration:

96 h

Dose descriptor:

EC50

Remarks:

(Class: Amides)

Effect conc.:

0 mg/L

Nominal / measured:

not specified

Conc. based on:

not specified

Basis for effect:

other: estimation by calculation

Remarks on result:

other: Note: Chemical may not be soluble enough to measure this predicted effect.

Duration:

96 h

Dose descriptor:

EC50

Remarks:

(Neutral Organic SAR)

Effect conc.:

0 mg/L

Nominal / measured:

not specified

Conc. based on:

not specified

Basis for effect:

other: estimation by calculation

Remarks on result:

other: Note: Chemical may not be soluble enough to measure this predicted effect.

Dose descriptor:

other: ChV

Remarks:

(Class: Amides)

Effect conc.:

0 mg/L

Nominal / measured:

not specified

Conc. based on:

not specified

Basis for effect:

other: estimation by calculation

Remarks on result:

other: ChV (chronic value, QSAR)

Remarks:

Note: Chemical may not be soluble enough to measure this predicted effect.

Dose descriptor:

other: ChV

Remarks:

(Neutral Organic SAR)

Effect conc.:

0 mg/L

Nominal / measured:

not specified

Conc. based on:

not specified

Basis for effect:

other: estimation by calculation

Remarks on result:

other: ChV (chronic value, QSAR)

Remarks:

Note: Chemical may not be soluble enough to measure this predicted effect.

Details on results:

ChV = 10^([log (LOEC x NOEC)]/2)

ECOSAR Program (v1.11) Results:

===============================

ECOSAR Version 1.11 Results Page

 

SMILES : O=C(NCCNC(=O)CCCCCCCCCCC(O)CCCCCC)CCCCCCCCCCC(O)CCCCCC

CHEM  : Octadecanamide, N,N -1,2-ethanediylbis[12-hydroxy-

CAS Num:

ChemID1:

MOL FOR: C38 H76 N2 O4

MOL WT : 625.04

Log Kow: 11.311    (EPISuite Kowwin v1.68 Estimate)

Log Kow:           (User Entered)

Log Kow:           (PhysProp DB exp value - for comparison only)

Melt Pt:           (User Entered for Wat Sol estimate)

Melt Pt:           (deg C, PhysProp DB exp value for Wat Sol estimate)

Wat Sol: 2.409E-008 (mg/L, EPISuite WSKowwin v1.43 Estimate)

Wat Sol:           (User Entered)

Wat Sol:           (PhysProp DB exp value)

 

 

--------------------------------------

Values used to Generate ECOSAR Profile

--------------------------------------

Log Kow: 11.311    (EPISuite Kowwin v1.68 Estimate)

Wat Sol: 2.409E-008 (mg/L, EPISuite WSKowwin v1.43 Estimate)

------------------------------

Class Specific LogKow Cut-Offs

------------------------------

If the log Kow of the chemical is greater than the endpoint specific cut-offs

presented below, then no effects at saturation are expected for those endpoints.

 

Amides :

-------

Maximum LogKow: >8.5 (LC50)

Maximum LogKow: >8.0 (EC50,ChV)

 

Baseline Toxicity SAR Limitations:

---------------------------------

Maximum LogKow: 5.0 (Fish 96-hr LC50; Daphnid LC50)

Maximum LogKow: 6.4 (Green Algae EC50)

Maximum LogKow: 8.0 (ChV)

Note: Chemical may not be soluble enough to measure this predicted effect. If the effect level exceeds the water solubility by 10X, typically no effects at saturation (NES)are reported.

Validity criteria fulfilled:

not applicable

Conclusions:

The calculated EC50 (96 h) for green algae of 12-hydroxy-N-[2-(12-hydroxyoctadecanoylamino)ethyl]octadecanamide is 9.61E-6 mg/L based on ECOSAR class Amides. The predicted EC50 (96 h) for the baseline toxicity (Neutral Organic SAR) is 7.79E-5 mg/L. The calculated chronic values (ChV) are 4.59E-4 mg/L (class Amides) and 1.38E-4 mg/L (Neutral Organic SAR), respectively. The chemical may not be soluble enough to measure the predicted effects.

Executive summary:

The aquatic toxicity for green algae of 12-hydroxy-N-[2-(12-hydroxyoctadecanoylamino)ethyl]octadecanamide is calculated by ECOSAR (v1.11), using EPI Suite. The calculated EC50 (96 h) is 9.61E-6 mg/L based on ECOSAR class Amides. The predicted EC50 (96 h) for the baseline toxicity (Neutral Organic SAR) is 7.79E-5 mg/L. The calculated chronic values (ChV) are 4.59E-4 mg/L (class Amides) and 1.38E-4 mg/L (Neutral Organic SAR), respectively. These values reflect high toxicity. However, the chemical may not be soluble enough to measure this predicted effect. Nevertheless, the estimation by calculation only provides an approximation and cannot replace empirical studies. The EPA recommends that EPI Suite is a screening-level tool and should not be used if acceptable measured values are available.

Reference 5

Endpoint:

toxicity to aquatic algae and cyanobacteria

Type of information:

(Q)SAR

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

accepted calculation method

Justification for type of information:

The toxicity to aquatic algae is estimated based on EPI Suite, ECOSAR v1.11. Two models are available, the estimation from the class (Amides) and the Baseline Toxicity (neutral organic structure activity relationship).

Principles of method if other than guideline:

The toxicity to aquatic algae is estimated based on EPI Suite, ECOSAR v1.11. Two models are available, the estimation from the class (Amides) and the Baseline Toxicity (neutral organic structure activity relationship).

GLP compliance:

no

Specific details on test material used for the study:

Calculation is based on the structure of the test material.
- Name of test material (as cited in study report): N,N'-(Benzene-1,3-diyldimethanediyl)bis(12-hydroxyoctadecanamide)

Analytical monitoring:

not required

Vehicle:

not specified

Test organisms (species):

other: Green algae, calculated

Test type:

other: estimation by calculation

Water media type:

not specified

Duration:

96 h

Dose descriptor:

EC50

Remarks:

(Class: Amides)

Effect conc.:

0 mg/L

Nominal / measured:

not specified

Conc. based on:

not specified

Basis for effect:

other: estimation by calculation

Remarks on result:

other: Note: Chemical may not be soluble enough to measure this predicted effect.

Duration:

96 h

Dose descriptor:

EC50

Remarks:

(Neutral Organic SAR)

Effect conc.:

0 mg/L

Nominal / measured:

not specified

Conc. based on:

not specified

Basis for effect:

other: estimation by calculation

Remarks on result:

other: Note: Chemical may not be soluble enough to measure this predicted effect.

Dose descriptor:

other: ChV

Remarks:

(Class: Amides)

Effect conc.:

0 mg/L

Nominal / measured:

not specified

Conc. based on:

not specified

Basis for effect:

other: estimation by calculation

Remarks on result:

other: ChV (chronic value, QSAR)

Remarks:

Note: Chemical may not be soluble enough to measure this predicted effect.

Dose descriptor:

other: ChV

Remarks:

(Neutral Organic SAR)

Effect conc.:

0 mg/L

Nominal / measured:

not specified

Conc. based on:

not specified

Basis for effect:

other: estimation by calculation

Remarks on result:

other: ChV (chronic value, QSAR)

Remarks:

Note: Chemical may not be soluble enough to measure this predicted effect.

Details on results:

ChV = 10^([log (LOEC x NOEC)]/2)

ECOSAR Program (v1.11) Results:

===============================

ECOSAR Version 1.11 Results Page

 

SMILES : CCCCCCC(CCCCCCCCCCC(=O)NCc1cc(ccc1)CNC(=O)CCCCCCCCCCC(CCCCCC)O)O

CHEM  : N,N'-(Benzene-1,3-diyldimethanediyl)bis(12-hydroxyoctadecanamide)

CAS Num:

ChemID1:

MOL FOR: C44 H80 N2 O4

MOL WT : 701.14

Log Kow: 13.075    (EPISuite Kowwin v1.68 Estimate)

Log Kow:           (User Entered)

Log Kow:           (PhysProp DB exp value - for comparison only)

Melt Pt:           (User Entered for Wat Sol estimate)

Melt Pt:           (deg C, PhysProp DB exp value for Wat Sol estimate)

Wat Sol: 2.351E-010 (mg/L, EPISuite WSKowwin v1.43 Estimate)

Wat Sol:           (User Entered)

Wat Sol:           (PhysProp DB exp value)

 

 

--------------------------------------

Values used to Generate ECOSAR Profile

--------------------------------------

Log Kow: 13.075    (EPISuite Kowwin v1.68 Estimate)

Wat Sol: 2.351E-010 (mg/L, EPISuite WSKowwin v1.43 Estimate)

 

------------------------------

Class Specific LogKow Cut-Offs

------------------------------

If the log Kow of the chemical is greater than the endpoint specific cut-offs

presented below, then no effects at saturation are expected for those endpoints.

 

Amides :

-------

Maximum LogKow: >8.5 (LC50)

Maximum LogKow: >8.0 (EC50,ChV)

 

Baseline Toxicity SAR Limitations:

---------------------------------

Maximum LogKow: 5.0 (Fish 96-hr LC50; Daphnid LC50)

Maximum LogKow: 6.4 (Green Algae EC50)

Maximum LogKow: 8.0 (ChV)

Note: Chemical may not be soluble enough to measure this predicted effect. If the effect level exceeds the water solubility by 10X, typically no effects at saturation (NES)are reported.

Validity criteria fulfilled:

not applicable

Conclusions:

The calculated EC50 (96 h) for green algae of N,N'-[1,3-Phenylenebis(methylene)bis[12-hydroxyoctadecanamide] is 8.64E-7 mg/L based on ECOSAR class Amides. The predicted EC50 (96 h) for the baseline toxicity (Neutral Organic SAR) is 5.25E-6 mg/L. The calculated chronic values (ChV) are 8.68E-5 mg/L (class Amides) and 1.34E-5 mg/L (Neutral Organic SAR), respectively. The chemical may not be soluble enough to measure the predicted effects.

Executive summary:

The aquatic toxicity for green algae of N,N'-[1,3-Phenylenebis(methylene)bis[12-hydroxyoctadecanamide] is calculated by ECOSAR (v1.11), using EPI Suite. The calculated EC50 (96 h) is 8.64E-7 mg/L based on ECOSAR class Amides. The predicted EC50 (96 h) for the baseline toxicity (Neutral Organic SAR) is 5.25E-6 mg/L. The calculated chronic values (ChV) are 8.68E-5 mg/L (class Amides) and 1.34E-5 mg/L (Neutral Organic SAR), respectively. These values reflect high toxicity. However, the chemical may not be soluble enough to measure this predicted effect. Nevertheless, the estimation by calculation only provides an approximation and cannot replace empirical studies. The EPA recommends that EPI Suite is a screening-level tool and should not be used if acceptable measured values are available.

Reference 6

Endpoint:

toxicity to aquatic algae and cyanobacteria

Type of information:

(Q)SAR

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

accepted calculation method

Justification for type of information:

The toxicity to aquatic algae is estimated based on EPI Suite, ECOSAR v1.11. Two models are available, the estimation from the class (Amides) and the Baseline Toxicity (neutral organic structure activity relationship).

Principles of method if other than guideline:

The toxicity to aquatic algae is estimated based on EPI Suite, ECOSAR v1.11. Two models are available, the estimation from the class (Amides) and the Baseline Toxicity (neutral organic structure activity relationship).

GLP compliance:

no

Specific details on test material used for the study:

Calculation is based on the structure of the test material.
- Name of test material (as cited in study report): Octadecanamide, N,N'-1,6-hexanediylbis 12-hydroxy-

Analytical monitoring:

not required

Vehicle:

not specified

Test organisms (species):

other: Green algae, calculated

Test type:

other: estimation by calculation

Water media type:

not specified

Duration:

96 h

Dose descriptor:

EC50

Remarks:

(Class: Amides)

Effect conc.:

0 mg/L

Nominal / measured:

not specified

Conc. based on:

not specified

Basis for effect:

other: estimation by calculation

Remarks on result:

other: Note: Chemical may not be soluble enough to measure this predicted effect.

Duration:

96 h

Dose descriptor:

EC50

Remarks:

(Neutral Organic SAR)

Effect conc.:

0 mg/L

Nominal / measured:

not specified

Conc. based on:

not specified

Basis for effect:

other: estimation by calculation

Remarks on result:

other: Note: Chemical may not be soluble enough to measure this predicted effect.

Dose descriptor:

other: ChV

Remarks:

(Class: Amides)

Effect conc.:

0 mg/L

Nominal / measured:

not specified

Conc. based on:

not specified

Basis for effect:

other: estimation by calculation

Remarks on result:

other: ChV (chronic value, QSAR)

Remarks:

Note: Chemical may not be soluble enough to measure this predicted effect.

Dose descriptor:

other: ChV

Remarks:

(Neutral Organic SAR)

Effect conc.:

0 mg/L

Nominal / measured:

not specified

Conc. based on:

not specified

Basis for effect:

other: estimation by calculation

Remarks on result:

other: ChV (chronic value, QSAR)

Remarks:

Note: Chemical may not be soluble enough to measure this predicted effect.

Details on results:

ChV = 10^([log (LOEC x NOEC)]/2)

ECOSAR Program (v1.11) Results:

===============================

ECOSAR Version 1.11 Results Page

 

SMILES : O=C(NCCCCCCNC(=O)CCCCCCCCCCC(O)CCCCCC)CCCCCCCCCCC(O)CCCCCC

CHEM  : Octadecanamide, N,N'-1,6-hexanediylbis 12-hydroxy-

CAS Num:

ChemID1:

MOL FOR: C42 H84 N2 O4

MOL WT : 681.15

Log Kow: 13.276    (EPISuite Kowwin v1.68 Estimate)

Log Kow:           (User Entered)

Log Kow:           (PhysProp DB exp value - for comparison only)

Melt Pt:           (User Entered for Wat Sol estimate)

Melt Pt:           (deg C, PhysProp DB exp value for Wat Sol estimate)

Wat Sol: 2.153E-010 (mg/L, EPISuite WSKowwin v1.43 Estimate)

Wat Sol:           (User Entered)

Wat Sol:           (PhysProp DB exp value)

 

 

--------------------------------------

Values used to Generate ECOSAR Profile

--------------------------------------

Log Kow: 13.276    (EPISuite Kowwin v1.68 Estimate)

Wat Sol: 2.153E-010 (mg/L, EPISuite WSKowwin v1.43 Estimate)

 

------------------------------

Class Specific LogKow Cut-Offs

------------------------------

If the log Kow of the chemical is greater than the endpoint specific cut-offs

presented below, then no effects at saturation are expected for those endpoints.

 

Amides :

-------

Maximum LogKow: >8.5 (LC50)

Maximum LogKow: >8.0 (EC50,ChV)

 

Baseline Toxicity SAR Limitations:

---------------------------------

Maximum LogKow: 5.0 (Fish 96-hr LC50; Daphnid LC50)

Maximum LogKow: 6.4 (Green Algae EC50)

Maximum LogKow: 8.0 (ChV)

Note: Chemical may not be soluble enough to measure this predicted effect. If the effect level exceeds the water solubility by 10X, typically no effects at saturation (NES)are reported.

Validity criteria fulfilled:

not applicable

Conclusions:

The calculated EC50 (96 h) for green algae of Octadecanamide, N,N'-1,6-hexanediylbis 12-hydroxy- is 6.3E-7 mg/L based on ECOSAR class Amides. The predicted EC50 (96 h) for the baseline toxicity (Neutral Organic SAR) is 3.71E-6 mg/L. The calculated chronic values (ChV) are 6.89E-5 mg/L (class Amides) and 9.87E-6 mg/L (Neutral Organic SAR), respectively. The chemical may not be soluble enough to measure the predicted effects.

Executive summary:

The aquatic toxicity for green algae of Octadecanamide, N,N'-1,6-hexanediylbis 12-hydroxy- is calculated by ECOSAR (v1.11), using EPI Suite. The calculated EC50 (96 h) is 6.3E-7 mg/L based on ECOSAR class Amides. The predicted EC50 (96 h) for the baseline toxicity (Neutral Organic SAR) is 3.71E-6 mg/L. The calculated chronic values (ChV) are 6.89E-5 mg/L (class Amides) and 9.87E-6 mg/L (Neutral Organic SAR), respectively. These values reflect high toxicity. However, the chemical may not be soluble enough to measure this predicted effect. Nevertheless, the estimation by calculation only provides an approximation and cannot replace empirical studies. The EPA recommends that EPI Suite is a screening-level tool and should not be used if acceptable measured values are available.

Description of key information

The substance consists of three structurally similar bisamides: N,N'-ethane-1,2-diylbis(12-hydroxyoctadecanamide), N,N'-hexane-1,6-diylbis(12-hydroxyoctadecanamide) and N,N'-[1,3-phenylenebis(methylene)]bis(12-hydroxyoctadecanamide). Experimental data on this substance are not available. The individual constituents and mixtures of them and similar amides are considered suitable read-across substances. In guideline studies on two read-across substances no toxicity was observed. Saturated solutions of 12-hydroxyoctadecanoic acid, reaction products with 1,3-benzenedimethanamine and hexamethylenediamine did not show adverse effects on Selenastrum capricornutum because the solubility of the test material was too low. In dispersions of 1,3-bis[12-hydroxy-octadecamide-N-methylene]-benzene slight growth inhibition of Pseudokirchneriella subcapitata was observed which was not related to toxicity but physical effects of the dispersed test material particles. Calculations on three constituents of the substance by the QSAR software tool EPI Suite v4.1.1 predicted that no effects at saturation on green algae are expected due to the low water solubility of the bisamides. Based on the experimental results on the read-across substances and the toxicity predictions for individual constituents by EPI Suite, the properties of the multi-constituent substance are expected to be comparable. Experiments on the aquatic toxicity are considered technically not feasible due to the low water solubility and no study was conducted. The CLP criteria are not met and the substance does not need to be classified.