(S)-2-methyl-5-(1-methylvinyl)cyclohex-2-en-1-one

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:

Data is from OECD QSAR toolbox version.3.3 and QMRF report has been attached.

Qualifier:

according to guideline

Guideline:

other: Predicted data

Principles of method if other than guideline:

Prediction is done using QSAR Toolbox version 3.3 with log kow as the primary discriptors.

GLP compliance:

no

Specific details on test material used for the study:

- Name of test material (IUPAC name): (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one- Common name: d-Carvone- Molecular formula: C10H14O- Molecular weight: 150.22 g/mol- Smiles notation: C1[C@H](CC=C(C1=O)C)C(C)=C- InChl: 1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m0/s1- Substance type: Organic- Physical state: Colorless to pale-yellow liquid

Analytical monitoring:

not specified

Vehicle:

not specified

Test organisms (species):

Daphnia magna

Test type:

static

Water media type:

freshwater

Limit test:

no

Total exposure duration:

48 h

Key result

Duration:

48 h

Dose descriptor:

EC50

Effect conc.:

249.516 mg/L

Nominal / measured:

estimated

Conc. based on:

test mat.

Basis for effect:

other: Intoxication

Remarks on result:

other: not toxic

The prediction was based on dataset comprised from the following descriptors: EC50
Estimation method: Takes average value from the 6 nearest neighbours
Domain  logical expression:Result: In Domain

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

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Aliphatic Carbon [CH] OR Aliphatic Carbon [-CH2-] OR Aliphatic Carbon [-CH3] OR Carbonyl, aliphatic attach [-C(=O)-] OR Carbonyl, olefinic attach [-C(=O)-] OR Miscellaneous sulfide (=S) or oxide (=O) OR Olefinic carbon [=CH- or =C<] OR Olefinic carbon [=CH2] OR Tertiary Carbon by Organic functional groups (US EPA) ONLY

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Allyl OR Cycloalkene OR Cycloketone OR Overlapping groups by Organic Functional groups (nested) ONLY

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Alkene OR Allyl OR Cycloalkene OR Cycloketone by Organic Functional groups 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 >> Nucleophilic addition to alpha, beta-unsaturated carbonyl compounds OR AN2 >> Nucleophilic addition to alpha, beta-unsaturated carbonyl compounds >> alpha, beta-Unsaturated Aldehydes OR AN2 >> Schiff base formation OR AN2 >> Schiff base formation >> alpha, beta-Unsaturated Aldehydes by DNA binding by OASIS v.1.3

Domain logical expression index: "f"

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

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as No Data by Ultimate biodeg

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as 0 to 1 day by Ultimate biodeg

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as No Data by Ultimate biodeg

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as 10 to 100 days by Ultimate biodeg

Domain logical expression index: "k"

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

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Aldehydes (Mono) by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as -C=CH  [alkenyl hydrogen] AND -CH -  [cyclic] AND -CH2-  [cyclic] AND Ketone   [-C-C(=O)-C-] AND Methyl  [-CH3] by Bioaccumulation - metabolism alerts

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as Carbon with 4 single bonds & no hydrogens by Bioaccumulation - metabolism alerts

Domain logical expression index: "o"

Referential boundary: The target chemical should be classified as -C=CH  [alkenyl hydrogen] AND -CH -  [cyclic] AND -CH2-  [cyclic] AND Ketone   [-C-C(=O)-C-] AND Methyl  [-CH3] by Bioaccumulation - metabolism alerts

Domain logical expression index: "p"

Referential boundary: The target chemical should be classified as -CH-   [linear] by Bioaccumulation - metabolism alerts

Domain logical expression index: "q"

Referential boundary: The target chemical should be classified as -C=CH  [alkenyl hydrogen] AND -CH -  [cyclic] AND -CH2-  [cyclic] AND Ketone   [-C-C(=O)-C-] AND Methyl  [-CH3] by Bioaccumulation - metabolism alerts

Domain logical expression index: "r"

Referential boundary: The target chemical should be classified as Linear C4 terminal chain  [CCC-CH3] by Bioaccumulation - metabolism alerts

Domain logical expression index: "s"

Referential boundary: The target chemical should be classified as -C=CH  [alkenyl hydrogen] AND -CH -  [cyclic] AND -CH2-  [cyclic] AND Ketone   [-C-C(=O)-C-] AND Methyl  [-CH3] by Bioaccumulation - metabolism alerts

Domain logical expression index: "t"

Referential boundary: The target chemical should be classified as Unsubstituted Cycloalkane by Bioaccumulation - metabolism alerts

Domain logical expression index: "u"

Referential boundary: The target chemical should be classified as Fast by Bioaccumulation - metabolism half-lives ONLY

Domain logical expression index: "v"

Similarity boundary:Target: CC(=C)C1CC=C(C)C(=O)C1
Threshold=50%,
Dice(Atom centered fragments)
Atom type; Count H attached; Hybridization

Domain logical expression index: "w"

Parametric boundary:The target chemical should have a value of log Kow which is >= 0.257

Domain logical expression index: "x"

Parametric boundary:The target chemical should have a value of log Kow which is <= 3.45

Conclusions:

Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the closest read across substances, the toxicity to aquatic invertebrate was predicted (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS: 2244-16-8). EC50 Intoxication value was estimated to be 249.516 mg/l for Daphnia magna for 48 hrs duration. It was concluded that (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS: 2244-16-8) was likely to be not toxic to aquatic invertebrate.

Executive summary:

Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the closest read across substances, the toxicity to aquatic invertebrate was predicted (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS: 2244-16-8). EC50 Intoxication value was estimated to be 249.516 mg/l for Daphnia magna for 48 hrs duration. It was concluded that (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS: 2244-16-8) was likely to be not toxic to aquatic invertebrate.

Description of key information

Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the closest read across substances, the toxicity to aquatic invertebrate was predicted (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS: 2244-16-8). EC50 Intoxication value was estimated to be 249.516 mg/l for Daphnia magna for 48 hrs duration. It was concluded that (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS: 2244-16-8) was likely to be not toxic to aquatic invertebrate.

Key value for chemical safety assessment

Fresh water invertebrates

Fresh water invertebrates

Effect concentration:

249.516 mg/L

Additional information

Following studies of target chemical and structurally similar read across includes predicted data and experimental data to conclude the toxicity extent of (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS: 2244-16-8) towards aquatic invertebrate is summarized as follows:

Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the closest read across substances, the toxicity to aquatic invertebrate was predicted (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS: 2244-16-8). EC50 Intoxication value was estimated to be 249.516 mg/l for Daphnia magna for 48 hrs duration. It was concluded that (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS: 2244-16-8) was likely to be not toxic to aquatic invertebrate.

The above predicted data of target chemical is supported by the experimental study of structurally similar read across Isophorone (CAS: 78 -59 -1) from the publication Bulletin of Environmental Contamination and Toxicology 1980, suggests that To study the effects of 1,1,3-Trimethyl-3-cyclohexene-5-one on aquatic invertebrate acute toxicity test was carried out for 48 hr under static condition. The chemical to be tested was added to 500 mL of diluent water in 2-L jars to prepare each test solution. If the chemical was soluble in the diluent water, then the 500 mL volume of test solution was divided into three, 150 mL aliquots in 250-mL beakers to provide triplicate exposures.

Observations of test populations were made at 24 and 48 hours of exposure and any mortalities were recorded. Lethal concentration LC50 to 50% of Daphnia magna when exposed to 1,1,3-Trimethyl-3-cyclohexene-5-one of 48 h is 120 mg/L. It can be concluded from the mortality value that the 1,1,3-Trimethyl-3-cyclohexene-5-one (CAS:78 -59 -1)  is not toxic to the aquatic invertebrate and can be considered as “not classified” as per the classification criteria for aquatic environment.

Another supporting experimental study for the structurally similar read across 2-Hydroxyethyl methacrylate (CAS: 868-77-9) from the (J check) 2018, also suggests that To study the effcts of 2-Hydroxyethyl methacrylate on invertebrate test was carried out according to the OECD Guideline 202 (Daphnia sp., Acute Immobilisation Test and Reproduction Test). The test was carried out under static condition at nominal concentrations of1000, 556, 309, 171, 95.3 mg/L (geometric ratio 1.8), control. Immobilization was measured during the test.Results after 24-hour exposure:- 50 % Effective concentration (EC50) for immobilization: 598 mg/L (95 % CL: 309 - 1000 mg/L), Results after 48-hour exposure:

- No observed effect concentration (NOEC) for immobilization: 171 mg/L,

- Lowest concentration causing 100 % immobility: 556 mg/L,(All results were based on the nominal values.)

The effective concentration EC50 to 50% of Daphnia magna when exposed to 2-Hydroxyethyl methacrylate for 48 hr is 380 mg/L.It can be concluded from the value that the 2-Hydroxyethyl methacrylate (CAS: 868-77-9) is not toxic/toxic to the aquatic invertebrate and can be considered as “not classified” as per the classification criteria for aquatic environment.

Thus based on the effect concentrations which is in the range 120 mg/L to380 mg/lgive the conclusion that test substance (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS: 2244-16-8) is likely to be not toxic to aquatic invertebrate at environmentally relevant concentrations and applying weight of evidence approach it can be considered to be “not classified” as per the CLP classification criteria.