Butane-1,2,3,4-tetracarboxylic acid

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Endpoint:

biodegradation in water: screening tests

Type of information:

(Q)SAR

Adequacy of study:

weight of evidence

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 limited documentation / justification

Justification for type of information:

The supporting QMRF report has been attached.

Qualifier:

according to guideline

Guideline:

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

Principles of method if other than guideline:

Prediction was done using OECD QSAR tool box v.3.3

GLP compliance:

not specified

Specific details on test material used for the study:

- Name( IUPAC): butane-1,2,3,4-tetracarboxylic acid- Name of test material (as cited in study report): 1,2,3,4­Butanetetracarboxylic acid, meso­-Molecular formula: C8H10O8-Molecular weight: 234.159 g/mol-Smilies notation: OC(=O)C[C@H]([C@H](CC(=O)O)C(=O)O)C(=O)O-InChI: 1S/C8H10O8/c9-5(10)1-3(7(13)14)4(8(15)16)2-6(11)12/h3-4H,1-2H2,(H,9,10)(H,11,12)(H,13,14)(H,15,16)/t3-,4+- Substance type: Organic- Physical state: white powder

Oxygen conditions:

aerobic

Inoculum or test system:

other: Microorganisms

Duration of test (contact time):

28 d

Parameter followed for biodegradation estimation:

other: BOD

Key result

Parameter:

other: BOD

Value:

86

Sampling time:

28 d

Remarks on result:

other: other details not available

Details on results:

The test chemical Butane-1,2,3,4-tetracarboxylic acid showed 86 % biodegradation in 28 days by BOD parameter.

The prediction was based on dataset comprised from the following descriptors: BOD
Estimation method: Takes average value from the 5 nearest neighbours
Domain  logical expression:Result: In Domain

((((((((("a" or "b" or "c" or "d" )  and ("e" and ( not "f") )  )  and ("g" and ( not "h") )  )  and ("i" and ( not "j") )  )  and "k" )  and "l" )  and ("m" and ( not "n") )  )  and ("o" and ( not "p") )  )  and ("q" and "r" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Carboxylic acid by Organic Functional groups

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Carboxylic acid by Organic Functional groups (nested)

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Acid, aliphatic attach [-COOH] AND Alcohol, olefinic attach [-OH] AND Aliphatic Carbon [CH] AND Aliphatic Carbon [-CH2-] AND Carbonyl, aliphatic attach [-C(=O)-] AND Miscellaneous sulfide (=S) or oxide (=O) AND Multi alcohol  AND Olefinic carbon [=CH- or =C<] AND Tertiary Carbon by Organic functional groups (US EPA)

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Carbonic acid derivative AND Carboxylic acid AND Carboxylic acid derivative by Organic functional groups, Norbert Haider (checkmol)

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as No alert found by DNA binding by OASIS v.1.3

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as AN2 OR AN2 >> Schiff base formation by aldehyde formed after metabolic activation OR AN2 >> Schiff base formation by aldehyde formed after metabolic activation >> Geminal Polyhaloalkane Derivatives OR AN2 >> Shiff base formation after aldehyde release OR AN2 >> Shiff base formation after aldehyde release >> Specific Acetate Esters OR AN2 >> Shiff base formation for aldehydes OR AN2 >> Shiff base formation for aldehydes >> Geminal Polyhaloalkane Derivatives OR AN2 >> Shiff base formation for aldehydes >> Haloalkane Derivatives with Labile Halogen OR Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> DNA Intercalators with Carboxamide Side Chain OR Radical OR Radical >> Radical mechanism via ROS formation (indirect) OR Radical >> Radical mechanism via ROS formation (indirect) >> Geminal Polyhaloalkane Derivatives OR Radical >> Radical mechanism via ROS formation (indirect) >> Nitrophenols, Nitrophenyl Ethers and Nitrobenzoic Acids OR Radical >> Radical mechanism via ROS formation (indirect) >> p-Substituted Mononitrobenzenes OR SN1 OR SN1 >> Nucleophilic attack after carbenium ion formation OR SN1 >> Nucleophilic attack after carbenium ion formation >> Specific Acetate Esters OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitrophenols, Nitrophenyl Ethers and Nitrobenzoic Acids OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> p-Substituted Mononitrobenzenes OR SN2 OR SN2 >> Acylation OR SN2 >> Acylation >> Specific Acetate Esters OR SN2 >> Acylation involving a leaving group  OR SN2 >> Acylation involving a leaving group  >> Geminal Polyhaloalkane Derivatives OR SN2 >> Acylation involving a leaving group  >> Haloalkane Derivatives with Labile Halogen OR SN2 >> Acylation involving a leaving group after metabolic activation OR SN2 >> Acylation involving a leaving group after metabolic activation >> Geminal Polyhaloalkane Derivatives OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom >> Haloalkane Derivatives with Labile Halogen OR SN2 >> Direct acting epoxides formed after metabolic activation OR SN2 >> Direct acting epoxides formed after metabolic activation >> Quinoline Derivatives OR SN2 >> DNA alkylation OR SN2 >> DNA alkylation >> Vicinal Dihaloalkanes OR SN2 >> Internal SN2 reaction with aziridinium and/or cyclic sulfonium ion formation (enzymatic) OR SN2 >> Internal SN2 reaction with aziridinium and/or cyclic sulfonium ion formation (enzymatic) >> Vicinal Dihaloalkanes OR SN2 >> Nucleophilic substitution at sp3 Carbon atom OR SN2 >> Nucleophilic substitution at sp3 Carbon atom >> Specific Acetate Esters OR SN2 >> Nucleophilic substitution at sp3 carbon atom after thiol (glutathione) conjugation OR SN2 >> Nucleophilic substitution at sp3 carbon atom after thiol (glutathione) conjugation >> Geminal Polyhaloalkane Derivatives OR SN2 >> SN2 at an activated carbon atom OR SN2 >> SN2 at an activated carbon atom >> Quinoline Derivatives by DNA binding by OASIS v.1.3

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as No alert found by DNA binding by OECD

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Michael addition OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Arenes OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Hydroquinones OR SN1 OR SN1 >> Iminium Ion Formation OR SN1 >> Iminium Ion Formation >> Aliphatic tertiary amines OR SN1 >> Nitrenium Ion formation OR SN1 >> Nitrenium Ion formation >> Aromatic azo OR SN1 >> Nitrenium Ion formation >> Primary aromatic amine OR SN1 >> Nitrenium Ion formation >> Secondary aromatic amine OR SN1 >> Nitrenium Ion formation >> Tertiary aromatic amine by DNA binding by OECD

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Non binder, non cyclic structure by Estrogen Receptor Binding

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Non binder, impaired OH or NH2 group OR Non binder, MW>500 OR Non binder, without OH or NH2 group OR Weak binder, OH group by Estrogen Receptor Binding

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as Low (Class I) by Toxic hazard classification by Cramer (original) ONLY

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Bioavailable by Lipinski Rule Oasis ONLY

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Group 14 - Carbon C AND Group 16 - Oxygen O by Chemical elements

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as Group 15 - Nitrogen N OR Group 16 - Sulfur S by Chemical elements

Domain logical expression index: "o"

Referential boundary: The target chemical should be classified as Carboxylic acid by Organic Functional groups

Domain logical expression index: "p"

Referential boundary: The target chemical should be classified as Acetoxy OR Alcohol OR Alkene OR Allyl OR Carboxylic acid ester OR Conjugated system OR Dihydroxyl group OR Maleate/ Fumarate OR Oxocarboxylic acid by Organic Functional groups

Domain logical expression index: "q"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 116 Da

Domain logical expression index: "r"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 258 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

readily biodegradable

Conclusions:

The test chemical Butane-1,2,3,4-tetracarboxylic acid showed 86 % biodegradation by considering BOD parameter and microorganisms as inoculum in 28 days.

Executive summary:

Biodegradability of test chemical Butane-1,2,3,4-tetracarboxylic acid is predicted using OECD QSAR tool box v.3.3 using log Kow as primary descriptor. The predicted value for biodegradation is 86 % by BOD parameter in 28 days therefore, it is concluded that this test chemical Butane-1,2,3,4 -tetracarboxylic acid is readily biodegradable.

Description of key information

Biodegradability of test chemical Butane-1,2,3,4-tetracarboxylic acid is predicted using OECD QSAR tool box v.3.3 using log Kow as primary descriptor. The predicted value for biodegradation is 86 % by BOD parameter in 28 days therefore, it is concluded that this test chemical Butane-1,2,3,4 -tetracarboxylic acid is readily biodegradable.

Key value for chemical safety assessment

Biodegradation in water:

readily biodegradable

Additional information

Predicted data for the target compound Butane-1,2,3,4-tetracarboxylic acid (CAS No. 1703 -58 -8) and supporting weight of evidence studies for its read across substance were reviewed for the biodegradation end point which are summarized as below.

Biodegradability of test chemical Butane-1,2,3,4-tetracarboxylic acid is predicted using OECD QSAR tool box v.3.3 using log Kow as primary descriptor. The predicted value for biodegradation is 86 % by BOD parameter in 28 days therefore, it is concluded that this test chemical Butane-1,2,3,4 -tetracarboxylic acid is readily biodegradable.

In a another prediction using the Estimation Programs Interface Suite (EPI suite, 2017) was run to predict the biodegradation potential of the test compound Butane-1,2,3,4- tetracarboxylic acid ( CAS no. 1703 -58 -8) in the presence of mixed populations of environmental microorganisms. The biodegradability of the substance was calculated using seven different models such as Linear Model, Non-Linear Model, Ultimate Biodegradation Timeframe, Primary Biodegradation Timeframe, MITI Linear Model, MITI Non-Linear Model and Anaerobic Model (called as Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that chemical butane-1,2,3,4-tetracarboxylic acid is expected to be readily biodegradable.

In supporting weight of evidence study from seconadry source ( J check) 2017 for read across chemical 1,10 -Decanedioic acid ( CAS no. 111 -20 -6) the experiment was carried out to test biodegradability by taking three parameters into consideration namely BOD, TOC and HPLC. The inoculums used for this experiment was activated sludge at 30mg/Concentration. The initial concentration of read across chemical taken was 100 mg/L.The biodegradability test was carried out for 28 days. The percent biodegradation of read across chemical obtained was 89 % by BOD parameter and 100% by parameter TOC and HPLC. All percentages are high, so it is concluded that read across chemical 1, 10-Decanedioic acid is readily biodegradable.

On the basis of above results of target chemical Butane-1,2,3,4 -tetracarboxylic acid ( From OECD QSAR tool box. v3.3 and EPI suite, 2017 ) and for its read across substance from secondary source it can be concluded that the target chemical Butane-1, 2, 3, 4- tetracarboxylic acid is expected to be readily biodegradable in nature.