Cinnamyl propionate

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 by using OECD QSAR tool box v.3.3

GLP compliance:

not specified

Specific details on test material used for the study:

- Name (IUPAC): (2E)-3-phenylprop-2-en-1-yl propanoate
- Molecular formula: C12H14O2
- Molecular weight: 190.241 g/mol
- Smiles notation: c1(\C=C\COC(CC)=O)ccccc1
- InChl: 1S/C12H14O2/c1-2-12(13)14-10-6-9-11-7-4-3-5-8-11/h3-9H,2,10H2,1H3/b9-6+
- Substance type: Organic
-Physical state: colourless pale yellow liquid

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:

89.167

Sampling time:

28 d

Remarks on result:

other: other details not available

Details on results:

Percent biodegradation of test chemical (2E)-3-phenylprop-2-en-1-yl propanoate estimated was 89.16 % in 28 days by considering 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" or "e" )  and "f" )  and "g" )  and "h" )  and "i" )  and "j" )  and ("k" and ( not "l") )  )  and ("m" and ( not "n") )  )  and ("o" and ( not "p") )  )  and ("q" and ( not "r") )  )  and ("s" and "t" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Esters (Acute toxicity) by US-EPA New Chemical Categories

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as SN2 AND SN2 >> SN2 Reaction at a sp3 carbon atom AND SN2 >> SN2 Reaction at a sp3 carbon atom >> Activated alkyl esters and thioesters  by Protein binding by OASIS v1.3

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as SN2 AND SN2 >> SN2 reaction at sp3 carbon atom AND SN2 >> SN2 reaction at sp3 carbon atom >> Allyl acetates and related chemicals by Protein binding by OECD

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Class 3 (unspecific reactivity) by Acute aquatic toxicity classification by Verhaar (Modified)

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as Esters AND Vinyl/Allyl Esters by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as Biodegrades Fast by Biodeg probability (Biowin 1) ONLY

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as Biodegrades Fast by Biodeg probability (Biowin 5) ONLY

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Biodegrades Fast by Biodeg probability (Biowin 6) ONLY

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Biodegrades Fast by Biodeg probability (Biowin 7) ONLY

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as weeks - months by Biodeg ultimate (Biowin 3) ONLY

Domain logical expression index: "k"

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

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as AN2 OR AN2 >> Schiff base formation OR AN2 >> Schiff base formation >> Polarized Haloalkene Derivatives OR AN2 >> Shiff base formation for aldehydes OR AN2 >> Shiff base formation for aldehydes >> Haloalkane Derivatives with Labile Halogen OR AN2 >> Thioacylation via nucleophilic addition after cysteine-mediated thioketene formation OR AN2 >> Thioacylation via nucleophilic addition after cysteine-mediated thioketene formation >> Haloalkenes with Electron-Withdrawing Groups OR AN2 >> Thioacylation via nucleophilic addition after cysteine-mediated thioketene formation >> Polarized Haloalkene Derivatives OR Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Coumarins OR Radical OR Radical >> Radical mechanism via ROS formation (indirect) OR Radical >> Radical mechanism via ROS formation (indirect) >> Coumarins OR SN2 OR SN2 >> Acylation involving a leaving group  OR SN2 >> Acylation involving a leaving group  >> Haloalkane Derivatives with Labile Halogen OR SN2 >> Alkylation, direct acting epoxides and related after P450-mediated metabolic activation OR SN2 >> Alkylation, direct acting epoxides and related after P450-mediated metabolic activation >> Haloalkenes with Electron-Withdrawing Groups 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 >> Coumarins OR SN2 >> DNA alkylation OR SN2 >> DNA alkylation >> Alkylphosphates, Alkylthiophosphates and Alkylphosphonates OR SN2 >> SN2 at sp3 and activated sp2 carbon atom OR SN2 >> SN2 at sp3 and activated sp2 carbon atom >> Polarized Haloalkene Derivatives by DNA binding by OASIS v.1.3

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Not possible to classify according to these rules by DPRA Lysine peptide depletion

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as High reactive OR High reactive >> Acrylic acid esters by DPRA Lysine peptide depletion

Domain logical expression index: "o"

Referential boundary: The target chemical should be classified as Not known precedent reproductive and developmental toxic potential by DART scheme v.1.0

Domain logical expression index: "p"

Referential boundary: The target chemical should be classified as Alkyl and vinyl nitriles< C6 atoms- sub category 25 (c, d) OR Known precedent reproductive and developmental toxic potential OR Non-steroid nucleus derived estrogen receptor (ER) and androgen receptor (AR) OR Non-steroid nucleus derived estrogen receptor (ER) and androgen receptor (AR) >> 4-alkylphenol-like derivatives (2b-3) by DART scheme v.1.0

Domain logical expression index: "q"

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: "r"

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

Domain logical expression index: "s"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 136 Da

Domain logical expression index: "t"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 242 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

readily biodegradable

Conclusions:

Percent biodegradation of test chemical (2E)-3-phenylprop-2-en-1-yl propanoate estimated was 89.16 % by considering BOD Parameter and microorganisms as a inoculum in 28 days.

Executive summary:

Biodegradability of test chemical (2E)-3-phenylprop-2-en-1-yl propanoate(CAS No.103-56-0) is predicted using OECD QSAR tool box v.3.3 using log Kow as primary descriptor. Percent Biodegradation of test chemical (2E)-3-phenylprop-2-en-1-yl propanoate estimated was 89.16 % by using BOD parameter and microorganisms as inoculum in 28 days. By this value of percent biodegradation it is concluded that test chemical (2E)-3-phenylprop-2-en-1-yl propanoate is readily biodegradable.

Description of key information

Biodegradability of test chemical (2E)-3-phenylprop-2-en-1-yl propanoate (CAS No.103-56-0) is predicted using OECD QSAR tool box v.3.3 using log Kow as primary descriptor. Percent Biodegradation of test chemical (2E)-3-phenylprop-2-en-1-yl propanoate estimated was 89.16 % by using BOD parameter and microorganisms as inoculum in 28 days. By this value of percent biodegradation it is concluded that test chemical (2E)-3-phenylprop-2-en-1-yl propanoate is readily biodegradable.

Key value for chemical safety assessment

Biodegradation in water:

readily biodegradable

Additional information

Predicted data for the target compound (2E)-3-phenylprop-2-en-1-ylpropanoate (CAS No.103-56-0) and supporting weight of evidence studies for its read across substance were reviewed for the biodegradation end point which is summarized as below:

Biodegradability of test chemical (2E)-3-phenylprop-2-en-1-yl propanoate(CAS No.103-56-0) was predicted using OECD QSAR tool box v.3.3 using log Kow as primary descriptor. Percent Biodegradation of test chemical (2E)-3-phenylprop-2-en-1-yl propanoate estimated was 89.16 % by using BOD parameter and microorganisms as inoculum in 28 days. By this value of percent biodegradation it is concluded that test chemical (2E)-3-phenylprop-2-en-1-yl propanoate is readily biodegradable.

Another prediction done by using Estimation Programs Interface Suite (EPI suite, 2017) to predict the biodegradation potential of the test compound (2E)-3-phenylprop-2-en-1-yl propanoate (CAS no.103-56-0) 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 (2E)-3-phenylprop-2-en-1-yl propanoateis expected to be readily biodegradable.

In a supporting weight of evidence study from authoritative database (J check, 2017) the Biodegradation experiment was carried out of read across chemical 2-dimethyaminoethyl methacrylat (CAS no. 2495-37-6) by taking activated sludge as inoculums at 30 mg/L concentration for 28 days. Biodegradation was analyzed by using two parameters that are O2 consumption (BOD), and test material analysis by HPLC .The initial concentration of read cross chemical was 100 mg/L and equipments used in study was of standard type. Read across chemical showed 81% degradation by O2 consumption parameter and 100% degradation by test material analysis parameter using HPLC. Therefore it is concluded that read across chemical 2-dimethyaminoethyl methacrylat is readily biodegradable.

In another supporting weight of evidence study of read across chemical (2E)-3-phenylprop-2-enoic acid (CAS no. 621-82-9)from Applied and Environmental Microbiology Journal (1979) the experiment was carried out to test the biodegradability of read across chemical (2E)-3-phenylprop-2-enoic acid (CAS no. 621-82-9) in serum bottles in anaerobic conditions at 35 oC temperature in dark. The pre-reduced defined medium was used in serum bottles with 1% v/v vitamin solution then it is inoculated10 % vol/vol seed from laboratory anaerobic digester fed primary settled sewage sludge on 15 day detention time. The anaerobic condition was attained by removing Oxygen from the medium by boiling, followed by the addition of the sodium sulfide reducing agent then Serum bottles (250-ml) were flushed (500 ml/min) with oxygen-free gas for 20 min before the inoculated medium was added. Sampling was done by using A 1-ml gas-tight glass syringe. The volume of gas produced by 250-ml serum-bottle cultures was measured daily by displacement of plunger lubricated with water in 20 mL glass syringe fitted with a 20 guage needle. The volume of gas (Methane and carbon dioxide) produced was equal to amount of degradation of substrate. The volume of gas produced by 250-ml serum-bottle cultures was measured daily by displacement of plunger lubricated with water in 20 mL glass syringe fitted with a 20 guage needle and Substrate concentration was determined by diluting a centrifuged sample and assaying it in a spectrophotometer at a known characteristic ultraviolet wavelength. After 28 days of incubation 87% biodegradability was observed of read cross chemical (2E)-3-phenylprop-2-enoic acid. So it is concluded that the chemical is readily biodegradable in anaerobic conditions.

 

On the basis of above results for target chemical (2E)-3-phenylprop-2-en-1-ylpropanoate (CAS No.103-56-0) (from OECD QSAR tool box and EPI suite, 2017) and for its read across substance (from authoritative database and Applied and Environmental Microbiology Journal ), it can be concluded that the test substance (2E)-3-phenylprop-2-en-1-ylpropanoate expected to be readily biodegradable in nature.