Cinnamyl butyrate

Short-term toxicity to aquatic invertebrates

Link to relevant study record(s)

Reference

Endpoint:

short-term toxicity to aquatic invertebrates

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:

other: estimated data

Principles of method if other than guideline:

The prediction was done by using OECD QSAR tool box v3.3

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of the test material: Cinnamyl butyrate
- IUPAC name: (2E)-3-phenylprop-2-en-1-yl butanoate
- Molecular formula: C13H16O2
- Molecular weight: 204.267 g/mol
- Substance type: Organic
- Smiles: c1(\C=C\COC(CCC)=O)ccccc1

Analytical monitoring:

not specified

Vehicle:

not specified

Test organisms (species):

Daphnia magna

Test type:

static

Water media type:

freshwater

Total exposure duration:

48 h

Duration:

48 h

Dose descriptor:

EC50

Effect conc.:

197.756 mg/L

Nominal / measured:

estimated

Conc. based on:

test mat.

Basis for effect:

other: Intoxication

Remarks on result:

other: not classified

The prediction was based on dataset comprised from the following descriptors: EC50
Estimation method: Takes average value from the 7 nearest neighbours
Domain  logical expression:Result: In Domain

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

Domain logical expression index: "a"

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

Domain logical expression index: "b"

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

Domain logical expression index: "c"

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

Domain logical expression index: "d"

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

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as AN2 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 >> 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 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 SN1 OR SN1 >> Carbenium ion formation OR SN1 >> Carbenium ion formation >> Alpha-Haloethers 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 >> Nitrobiphenyls and Bridged Nitrobiphenyls 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  >> 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 >> Alkylation, nucleophilic substitution at sp3-carbon atom >> Sulfonates and Sulfates OR SN2 >> Direct acting epoxides formed after metabolic activation OR SN2 >> Direct acting epoxides formed after metabolic activation >> Coumarins OR SN2 >> Direct acting epoxides formed after metabolic activation >> Quinoline Derivatives OR SN2 >> Nucleophilic substitution at sp3 Carbon atom OR SN2 >> Nucleophilic substitution at sp3 Carbon atom >> Specific Acetate Esters OR SN2 >> SN2 at an activated carbon atom OR SN2 >> SN2 at an activated carbon atom >> Quinoline Derivatives OR SN2 >> SN2 at sp3-carbon atom OR SN2 >> SN2 at sp3-carbon atom >> Alpha-Haloethers by DNA binding by OASIS v.1.3

Domain logical expression index: "f"

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

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as Michael addition OR Michael addition >> P450 Mediated Activation of Heterocyclic Ring Systems OR Michael addition >> P450 Mediated Activation of Heterocyclic Ring Systems >> Furans 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 SN1 OR SN1 >> Carbenium Ion Formation OR SN1 >> Carbenium Ion Formation >> Allyl benzenes OR SN1 >> Iminium Ion Formation OR SN1 >> Iminium Ion Formation >> Aliphatic tertiary amines OR SN1 >> Nitrenium Ion formation OR SN1 >> Nitrenium Ion formation >> Secondary aromatic amine OR SN2 OR SN2 >> SN2 at an sp3 Carbon atom OR SN2 >> SN2 at an sp3 Carbon atom >> Sulfonates by DNA binding by OECD

Domain logical expression index: "h"

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

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Reactive unspecified by Acute aquatic toxicity MOA by OASIS ONLY

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Aromatic-H AND Benzene AND -C=CH  [alkenyl hydrogen] AND -CH2-  [linear] AND Ester   [-C(=O)-O-C] AND Methyl  [-CH3] AND Unsubstituted phenyl group (C6H5-) by Bioaccumulation - metabolism alerts

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as Alkyl substituent on aromatic ring by Bioaccumulation - metabolism alerts

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Aromatic-H AND Benzene AND -C=CH  [alkenyl hydrogen] AND -CH2-  [linear] AND Ester   [-C(=O)-O-C] AND Methyl  [-CH3] AND Unsubstituted phenyl group (C6H5-) by Bioaccumulation - metabolism alerts

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Aomatic Sulfur by Bioaccumulation - metabolism alerts

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as Aromatic-H AND Benzene AND -C=CH  [alkenyl hydrogen] AND -CH2-  [linear] AND Ester   [-C(=O)-O-C] AND Methyl  [-CH3] AND Unsubstituted phenyl group (C6H5-) by Bioaccumulation - metabolism alerts

Domain logical expression index: "o"

Referential boundary: The target chemical should be classified as Aromatic ether  [-O-aromatic carbon] by Bioaccumulation - metabolism alerts

Domain logical expression index: "p"

Referential boundary: The target chemical should be classified as Alkene AND Allyl AND Aryl AND Carboxylic acid ester by Organic Functional groups

Domain logical expression index: "q"

Referential boundary: The target chemical should be classified as Alkane, branched with tertiary carbon by Organic Functional groups

Domain logical expression index: "r"

Parametric boundary:The target chemical should have a value of log Kow which is >= 0.225

Domain logical expression index: "s"

Parametric boundary:The target chemical should have a value of log Kow which is <= 4.82

Validity criteria fulfilled:

not specified

Conclusions:

The EC50 value was estimated to be 197.075 mg/L when test chemical(2E)-3-phenylprop-2-en-1-yl butanoate was exposed to daphnia magna for 48hrs.

Executive summary:

Short term toxicity to test chemical (2E)-3-phenylprop-2-en-1-yl butanoate was determined bu using OECD QSAR tool box v3.3 using seven closest read across chemical using log Kow as primary descriptor. The EC50 value was estimated to be 197.075  mg/L when test chemical(2E)-3-phenylprop-2-en-1-yl butanoate was exposed to daphnia magna for 48hrs. On the basis of EC50 value it is concluded that this test chemical is considered as not classified according to CLP classification criteria.

Description of key information

Short term toxicity to test chemical (2E)-3-phenylprop-2-en-1-yl butanoate was determined bu using OECD QSAR tool box v3.3 using seven closest read across chemical using log Kow as primary descriptor. The EC50 value was estimated to be 197.075  mg/L when test chemical(2E)-3-phenylprop-2-en-1-yl butanoate was exposed to daphnia magna for 48 hrs. On the basis of EC50 value it is concluded that this test chemical is considered as not classified according to CLP classification criteria.

Key value for chemical safety assessment

Fresh water invertebrates

Fresh water invertebrates

Effect concentration:

197.075 mg/L

Additional information

Results of predicted data for target chemical (2E)-3-phenylprop-2-en-1-yl butanoate (CAS no. 103-61-7) and experimental studies for its structurally similar read across chemicals for short term toxicity to aquatic invertebrate endpoint are summarized below.

In first weight of evidence study the Short term toxicity of test chemical (2E)-3-phenylprop-2-en-1-yl butanoate was determined by using OECD QSAR tool box v3.3 using seven closest read across chemical using log Kow as primary descriptor. The EC50 value was estimated to be 197.075 mg/L when test chemical (2E)-3-phenylprop-2-en-1-yl butanoate was exposed to daphnia magna for 48hrs. On the basis of EC50 value it is concluded that this test chemical is considered as not classified according to CLP classification criteria.

Next weight of evidence study was done from the peer reviewed journal Pakistan J. Zool., vol. 39(5), pp. 339-344, 2007 in this study the naturally occurring compounds including read across chemical 2-phenylethyl propanoate structurally similar to target chemical have been tested for molluscicidal activity against the fresh water snail, Biomphalaria alexandrina. The recommended World Health Organization bioassay procedure (WHO, 1965), was used for the evaluation of 2-phenylethyl propanoate on B. alexandrina. For this experiment the Biomphalaria alexandrina species 8mm ± 2mm diameter were collected from fresh water ponds at Kafr El-Dwar, Behera Governorate, Egypt and were maintained in glass aquaria oxygenated for one hour daily, one week before testing. The tests were performed in 150 mL glass beakers with ten adult healthy snails per assay. Each chemical was mixed with Tween 20, to ensure complete solubility of the chemical in water. The mixture was added to the glass beaker filled up to 100 ml of the dechlorinated water to give the desired concentration (w/v) up to 400 μg/ml of read cross chemical. The snails were exposed for 24 h to different concentrations of reas across chemical or their mixture with PB and then transferred to dechlorinated water for another 48 h. Percentage kill were recorded after 72 h. Percentage mortality was corrected using Abbott's formula (Abbott, 1925). Toxicity parameters for each treatment were computed according to the probit-analysis method by Finney (1971). According to experimental result the lethal concentration (LC50) value of read across chemical phenethyl propionate in aquatic invertebrate (Biomphalaria alexandrina) in a 72 hr study on the basis of mortality effect was determined to be 296.27 mg/L. It can be concluded from the value that the phenethyl propionate is not toxic to the aquatic invertebrate and can be considered as "not classified" as per the classification criteria.

Last experimental weight of evidence study was done from authoritative database (HSDB, 2017) for read across chemical Butanoic acid, ethyl ester (CAS no. 105-54-4) structuraaly similarly to target chemical in this study the short term toxicity to aquatic invertebrate Daphnia Magna was determined by exposing it to fresh water containing read across chemical Butanoic acid, ethyl ester in static condition. LC50 value was determined to be 755 mg/L on the basis of mortality of daphnia magna at temperature 20-22 oC and pH 7.6-7.7. Since LC 50 value is greater than 100 mg/L read across chemical Butanoic acid, ethyl ester is considered as not classified according to CLP classification criteria.

By considering results of all the experimental and predicted data studies mentioned above it is concluded that the target chemical (2E)-3-phenylprop-2-en-1-yl butanoate (CAS no. 103-61-7) is non toxic to aquatic invertebrate and considered as not classified according to CLP classification criteria.