Dimethyl maleate

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

(Q)SAR

Adequacy of study:

other information

Study period:

22 March 2023

Reliability:

2 (reliable with restrictions)

Prediction of biodegradability using BIOWIN

BIOWIN v4.10 predictions

SMILES : O=C(OCC)C=CC(=O)OCC
CHEM :
MOL FOR: C8 H12 O4
MOL WT : 172.18
--------------------------- BIOWIN v4.10 Results ----------------------------
Biowin1 (Linear Model Prediction) : Biodegrades Fast
Biowin2 (Non-Linear Model Prediction): Biodegrades Fast
Biowin3 (Ultimate Biodegradation Timeframe): Weeks
Biowin4 (Primary Biodegradation Timeframe): Days
Biowin5 (MITI Linear Model Prediction) : Readily Degradable
Biowin6 (MITI Non-Linear Model Prediction): Readily Degradable
Biowin7 (Anaerobic Model Prediction): Biodegrades Fast
Ready Biodegradability Prediction: YES
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin1 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 0.1742 | 0.3484
MolWt| * | Molecular Weight Parameter | | -0.0820
Const| * | Equation Constant | | 0.7475
============+============================================+=========+=========
RESULT | Biowin1 (Linear Biodeg Probability) | | 1.0139
============+============================================+=========+=========
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin2 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 4.0795 | 8.1590
MolWt| * | Molecular Weight Parameter | | -2.4450
============+============================================+=========+=========
RESULT | Biowin2 (Non-Linear Biodeg Probability) | | 0.9998
============+============================================+=========+=========
A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast
A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast
------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin3 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 0.1402 | 0.2804
MolWt| * | Molecular Weight Parameter | | -0.3805
Const| * | Equation Constant | | 3.1992
============+============================================+=========+=========
RESULT | Biowin3 (Survey Model - Ultimate Biodeg) | | 3.0991
============+============================================+=========+=========
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin4 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 0.2290 | 0.4579
MolWt| * | Molecular Weight Parameter | | -0.2484
Const| * | Equation Constant | | 3.8477
============+============================================+=========+=========
RESULT | Biowin4 (Survey Model - Primary Biodeg) | | 4.0572
============+============================================+=========+=========
Result Classification: 5.00 -> hours 4.00 -> days 3.00 -> weeks
(Primary & Ultimate) 2.00 -> months 1.00 -> longer
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin5 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 0.3437 | 0.6875
Frag | 2 | Methyl [-CH3] | 0.0004 | 0.0008
Frag | 2 | -CH2- [linear] | 0.0494 | 0.0988
Frag | 2 | -C=CH [alkenyl hydrogen] | 0.0062 | 0.0124
MolWt| * | Molecular Weight Parameter | | -0.5122
Const| * | Equation Constant | | 0.7121
============+============================================+=========+=========
RESULT | Biowin5 (MITI Linear Biodeg Probability) | | 0.9994
============+============================================+=========+=========
------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin6 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 2.4462 | 4.8923
Frag | 2 | Methyl [-CH3] | 0.0194 | 0.0389
Frag | 2 | -CH2- [linear] | 0.4295 | 0.8590
Frag | 2 | -C=CH [alkenyl hydrogen] | 0.0285 | 0.0570
MolWt| * | Molecular Weight Parameter | | -4.9707
============+============================================+=========+=========
RESULT |Biowin6 (MITI Non-Linear Biodeg Probability)| | 0.9678
============+============================================+=========+=========
A Probability Greater Than or Equal to 0.5 indicates --> Readily Degradable
A Probability Less Than 0.5 indicates --> NOT Readily Degradable
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin7 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 0.1719 | 0.3437
Frag | 2 | Methyl [-CH3] | -0.0796 | -0.1591
Frag | 2 | -CH2- [linear] | 0.0260 | 0.0520
Frag | 2 | -C=CH [alkenyl hydrogen] | -0.0735 | -0.1470
Const| * | Equation Constant | | 0.8361
============+============================================+=========+=========
RESULT | Biowin7 (Anaerobic Linear Biodeg Prob) | | 0.9256
============+============================================+=========+=========
A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast
A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast

Results of BIOWIN prediction for this substance:
Biowin3 (Ultimate Biodegradation Timeframe): Weeks
Biowin5 (MITI Linear Model Prediction): Readily Degradable

Conclusions:

Based on the above criteria, the prediction for this substance is: readily biodegradable.

Executive summary:

The ready biodegradability of the substance was predicted using BIOWIN v4.10.1 The biodegradability prediction for this substance is: readily biodegradable
This prediction report solely displays the output of BIOWIN v4.10. It serves the intention to be used as supporting information for a registration of an intermediate under EU REACH according to Art. 17, i.e. no formal data information requirements apply.

Reference 2

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

experimental study

Adequacy of study:

other information

Reliability:

4 (not assignable)

Rationale for reliability incl. deficiencies:

secondary literature

Qualifier:

according to guideline

Guideline:

OECD Guideline 301 B (Ready Biodegradability: CO2 Evolution Test)

GLP compliance:

yes

Interpretation of results:

readily biodegradable

Reference 3

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

experimental study

Adequacy of study:

other information

Reliability:

3 (not reliable)

Rationale for reliability incl. deficiencies:

significant methodological deficiencies

Remarks:

Validity criteria not fullfilled as the difference between two replicates is > 20%.

Qualifier:

according to guideline

Guideline:

OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I))

Deviations:

no

GLP compliance:

not specified

Oxygen conditions:

aerobic

Inoculum or test system:

other: sludge sampling from different sewage plants, natural waterbodies and soil

Details on inoculum:

1. Sludge sampling sites and time

1.1. Time: in March, June, September, and December, sludge was sampled
1.2. Sites (Japan): 1. Fukogawa city sewage plant, 2. Fukashiba industry sewage plant, 3. Nakahama city sewage plant, 4. Ochiai city sewage plant, 5. Kitakami river, 6. Shinano river, 7. Yoshino river, 8. Lake Biwa, 9. Hiroshima bay, 10. Dookai bay
A mixture composed of city and industry sewage and river, lake and sea surface water and soil was tested.

2. Sludge sampling method

2.1. City sewage: Returned sludge from sewage plants was taken.
2.2. Rivers, lake and sea: Surface water and surface soil which were in contact with atmosphere were collected.

3. Method of cultivation

3.1. Mixing of fresh and old activated sludge: 5 L of the filtrate of the supernatant of old activated sludge was mixed with 500 mL of the filtrate of the supernatant of new sludge and cultured at pH 7.0 ± 1.0 under sufficient aeration using prefiltered open air.

3.2. Culture: About 30 minutes after ceasing aeration to the sludge mixture, supernatant corresponding to about 1/3 of the whole volume was removed. Then the equal volume of dechlorinated water was added to the remaining portion and aerated again, followed by addition of synthetic sewage at aconcentration of 0.1% (w/v). This procedure was repeated once every day. The culturing was carried out at 25 ± 2 °C.

3.3. Control: During the cultivation, appearance of the supernatant, precipitability, formation of flock, pH, dissolved oxygen concentration in the solution and temperature were checked and necessary adjustments were made, Microflora in the activated sludge was microscopically observed and sludge with no abnormal symptom was used for the test.

4. Inspection of activity

Activity of the sludge was inspected to use reference substance. And the relation between new and old activated sludge was taken account.

5. Adaptation

There is no specific statement about the adaptation of the used microorganisms but the sampling sides and culture conditions suggest not adapted microorganisms.

6. Concentration of sludge: 30 mg/L

Duration of test (contact time):

28 d

Initial conc.:

100 mg/L

Based on:

test mat.

Parameter followed for biodegradation estimation:

O2 consumption

Remarks:

(indirect analysis, expressed as BOD)

Parameter followed for biodegradation estimation:

TOC removal

Remarks:

(direct analysis, expressed as TOC)

Parameter followed for biodegradation estimation:

test mat. analysis

Remarks:

(direct analysis, analytical method: GC)

Details on study design:

Test performed in open system: no
Preparation of basal culture medium (sludge):
- Suspended solids concentration: determined according to Method Japanese Industrial Standards (JIS) K 0102-1986-14.1
- Composition of basal culture medium: 3 mL each of four stock solutions, as described in JIS K 0102-1986-21, are diluted to 1000 mL with purified water
- pH of basal culture medium: 7.0
- pH adjusted: yes
Test system:
- Abiotic sterile control: 300 ml purified water + 30 mg test substance
- Test solution: 300 ml basal culture medium (sludge) + 30 mg test substance
- Reference: 300 ml basal culture medium (sludge) + 30 mg aniline
- Inoculum blank: 300 ml sludge
Test instruments and conditions:
- Culturing apparatus: Closed system oxygen consumption measuring apparatus (Coulometer: Ohkura Electric Co., Ltd.)
- Vessel size: 300 mL in volume
- absorbent for evolving carbon dioxide: Soda lime No .l (extra pure reagent, Wako Pure Chemical Industries, Ltd.).
- stirring method: test solution was stirred by a magnetic stirrer
- cultivating temperature: 25 ± 1°C
- reference substance: aniline
Analysis after termination of the test:
- TOC
- test substance
- pH

Degradation (%) was obtained from the following equations:
BOD: Degradation (%) = (BOD-B)/ThOD x 100 BOD (mg):
BOD in (sludge + m-Nitrotoluene system)
B (mg): BOD in sludge blank
ThOD: theoretical oxygen demand
required when m-Nitrotoluene was completely oxidized.

Reference substance:

aniline

Parameter:

% degradation (O2 consumption)

Value:

50 - 72

Sampling time:

28 d

Parameter:

% degradation (TOC removal)

Value:

65 - 97

Sampling time:

28 d

Parameter:

% degradation (test mat. analysis)

Value:

63 - 100

Sampling time:

28 d

Interpretation of results:

readily biodegradable

Conclusions:

In a modified MITI I test according to OECD guideline 301 C a non adapted mixed microbial inoculum mineralised 50 -72 % on the upward trend of the initial test substance concentration within 28 days (MITI, 1992). The interpretation of results as "Judgement: Ready biodegradability" is provided by the National Institute of Technology and Evaluation (NITE) in its on-line release, and December 28th, 1989 is reported as the "published date".

Reference 4

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

(Q)SAR

Adequacy of study:

other information

Study period:

22 March 2023

Reliability:

2 (reliable with restrictions)

Prediction of biodegradability using BIOWIN
BIOWIN v4.10 predictions
SMILES : O=C(OC)C=CC(=O)OC
CHEM :
MOL FOR: C6 H8 O4
MOL WT : 144.13

--------------------------- BIOWIN v4.10 Results ----------------------------
Biowin1 (Linear Model Prediction) : Biodegrades Fast
Biowin2 (Non-Linear Model Prediction): Biodegrades Fast
Biowin3 (Ultimate Biodegradation Timeframe): Weeks
Biowin4 (Primary Biodegradation Timeframe): Days
Biowin5 (MITI Linear Model Prediction) : Readily Degradable
Biowin6 (MITI Non-Linear Model Prediction): Readily Degradable
Biowin7 (Anaerobic Model Prediction): Biodegrades Fast
Ready Biodegradability Prediction: YES
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin1 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 0.1742 | 0.3484
MolWt| * | Molecular Weight Parameter | | -0.0686
Const| * | Equation Constant | | 0.7475
============+============================================+=========+=========
RESULT | Biowin1 (Linear Biodeg Probability) | | 1.0273
============+============================================+=========+=========
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin2 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 4.0795 | 8.1590
MolWt| * | Molecular Weight Parameter | | -2.0466
============+============================================+=========+=========
RESULT | Biowin2 (Non-Linear Biodeg Probability) | | 0.9999
============+============================================+=========+=========
A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast
A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin3 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 0.1402 | 0.2804
MolWt| * | Molecular Weight Parameter | | -0.3185

Const| * | Equation Constant | | 3.1992
============+============================================+=========+=========
RESULT | Biowin3 (Survey Model - Ultimate Biodeg) | | 3.1611
============+============================================+=========+=========
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin4 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 0.2290 | 0.4579
MolWt| * | Molecular Weight Parameter | | -0.2079
Const| * | Equation Constant | | 3.8477
============+============================================+=========+=========
RESULT | Biowin4 (Survey Model - Primary Biodeg) | | 4.0977
============+============================================+=========+=========
Result Classification: 5.00 -> hours 4.00 -> days 3.00 -> weeks
(Primary & Ultimate) 2.00 -> months 1.00 -> longer
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin5 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 0.3437 | 0.6875
Frag | 2 | Methyl [-CH3] | 0.0004 | 0.0008
Frag | 2 | -C=CH [alkenyl hydrogen] | 0.0062 | 0.0124
MolWt| * | Molecular Weight Parameter | | -0.4288
Const| * | Equation Constant | | 0.7121
============+============================================+=========+=========
RESULT | Biowin5 (MITI Linear Biodeg Probability) | | 0.9840
============+============================================+=========+=========
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin6 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 2.4462 | 4.8923
Frag | 2 | Methyl [-CH3] | 0.0194 | 0.0389
Frag | 2 | -C=CH [alkenyl hydrogen] | 0.0285 | 0.0570

MolWt| * | Molecular Weight Parameter | | -4.1608
============+============================================+=========+=========
RESULT |Biowin6 (MITI Non-Linear Biodeg Probability)| | 0.9662
============+============================================+=========+=========
A Probability Greater Than or Equal to 0.5 indicates --> Readily Degradable
A Probability Less Than 0.5 indicates --> NOT Readily Degradable
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin7 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 0.1719 | 0.3437
Frag | 2 | Methyl [-CH3] | -0.0796 | -0.1591
Frag | 2 | -C=CH [alkenyl hydrogen] | -0.0735 | -0.1470
Const| * | Equation Constant | | 0.8361
============+============================================+=========+=========
RESULT | Biowin7 (Anaerobic Linear Biodeg Prob) | | 0.8736
============+============================================+=========+=========
A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast
A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast

Results of BIOWIN prediction for this substance:
Biowin3 (Ultimate Biodegradation Timeframe): Weeks
Biowin5 (MITI Linear Model Prediction): Readily Degradable

Conclusions:

Based on the above criteria, the prediction for this substance is: readily biodegradable.

Executive summary:

The ready biodegradability of the substance was predicted using BIOWIN v4.10. The biodegradability prediction for this substance is: readily biodegradable
This prediction report solely displays the output of BIOWIN v4.10. It serves the intention to be used as supporting information for a registration of an intermediate under EU REACH according to Art. 17, i.e. no formal data information requirements apply.

Description of key information

The OECD 301C study to test the biodegradation of dimethyl maleate, indicates that the substance is readily biodegradable. However, the difference between two replicates is > 20% and thus the test is not considered valid.

Therefore, the biodegradation behavior of the analogue structure Diethyl maleate was considered. Diethyl maleate, which has 2 ethyl-moieties wheares dimethyl maleate has 2 methyl-moieties, was tested as readily biodegradable.

To confirm the study results of dimethyl maleat and diethyl maleate and to support the read-across from diethyl maleate to dimethyl maleate, the biodegradation potential was calculated with BIOWIN v4.10. Both substances were predicated as "readily biodegradable". 

Therefore it is plausible to assume that dimethyl maleate is readily biodegradable.