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

Bioaccumulation: aquatic / sediment

Link to relevant study record(s)

Reference

Endpoint:

bioaccumulation in aquatic species, other

Type of information:

calculation (if not (Q)SAR)

Adequacy of study:

weight of evidence

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

accepted calculation method

Justification for type of information:

Data is from computational model developed by USEPA

Qualifier:

according to guideline

Guideline:

other: Modeling database

Principles of method if other than guideline:

Prediction done using BCFBAF (v3.01) model

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material: d-Carvone- IUPAC name: (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one- Molecular formula: C10H14O- Molecular weight: 150.22 g/mole- Smiles :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

Radiolabelling:

not specified

Vehicle:

not specified

Test organisms (species):

other: Fish

Route of exposure:

aqueous

Test type:

other: estimation

Water / sediment media type:

natural water: freshwater

Test temperature:

25 deg.C

Reference substance (positive control):

not specified

Key result

Temp.:

25 °C

Type:

BCF

Value:

28.51 L/kg

Basis:

whole body w.w.

Calculation basis:

other: estimated

Remarks on result:

other: Non-bioaccumulative

BCFBAF Program (v3.01) Results:

==============================

SMILES : C1C(CC=C(C1(=O))C)C(C)=C

CHEM :

MOL FOR: C10 H14 O1

MOL WT : 150.22

--------------------------------- BCFBAF v3.01 --------------------------------

Summary Results:

Log BCF (regression-based estimate): 1.46 (BCF = 28.5 L/kg wet-wt)

Biotransformation Half-Life (days) : 0.528 (normalized to 10 g fish)

Log BAF (Arnot-Gobas upper trophic): 1.64 (BAF = 43.4 L/kg wet-wt)

Log Kow (experimental): 2.71

Log Kow used by BCF estimates: 2.71

Equation Used to Make BCF estimate:

Log BCF = 0.6598 log Kow - 0.333 + Correction

Correction(s): Value

No Applicable Correction Factors

Estimated Log BCF = 1.455 (BCF = 28.51 L/kg wet-wt)

Validity criteria fulfilled:

not specified

Conclusions:

Using BCFBAF Program (v3.00) model of EPI suite (2017) the estimated bio concentration factor (BCF) for (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS No. 2244-16-8) is 28.51 L/kg wet-wt at 25 deg. c which does not exceed the bioconcentration threshold of 2000. Therefore it is concluded that test chemical (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one is non bioaccumulative in food chain.

Executive summary:

Using BCFBAF Program (v3.00) model of EPI suite (2017) the estimated bio concentration factor (BCF) for (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS No. 2244-16-8) is 28.51 L/kg wet-wt at 25 deg. c which does not exceed the bioconcentration threshold of 2000. Therefore it is concluded that test chemical (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one is non bioaccumulative in food chain.

Description of key information

Using BCFBAF Program (v3.00) model of EPI suite (2017) the estimated bio concentration factor (BCF) for (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS No. 2244-16-8) is 28.51 L/kg wet-wt at 25 deg. c which does not exceed the bioconcentration threshold of 2000. Therefore it is concluded that test chemical (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one is non bioaccumulative in food chain.

Key value for chemical safety assessment

BCF (aquatic species):

28.51 dimensionless

Additional information

Various predicted data for the target compound(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS No. 2244-16-8)and supporting weight of evidence study for its structurally similar read across chemical were reviewed for the bioaccumulation end point which are summarized as below:

The first weight of evidence study was done by using BCFBAF Program (v3.00) model of Estimation Program Interface (EPI suite 2017) the estimated bio concentration factor (BCF) for (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS No. 2244-16-8) is 28.51 L/kg wet-wt at 25 deg. c

 

Second weight of evidence study was done by using Bio-concentration Factor (v12.1.0.50374) module of(ACD (Advanced Chemistry Development)/I-Lab predictive module, 2017) module in this study the Bio-concentration Factor at range pH 1-14  of the chemical (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one(CAS no.2244 -16 -8) estimated to be 31.0 dimensionless.

 

Next weight of evidence study was done by using Scifinder database of American Chemical Society (ACS, 2017) in this study the Bioconcentration factor (BCF) of test substance (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one at pH 1-10 and temperature 25 °C was estimated to be 31.2 dimensionless.  This BCF value at pH 1-10 and temperature 25 °C suggests that the test chemical (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one is non bioaccumulative in aquatic organisms.

 

Another weight of evidence study was done by using Chemspider- ACD/PhysChem Suite of Royal Society of Chemistry (RCS, 2017) in this study the Bioconcentration factor (BCF) of test substance (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one at pH 5.5 and pH 7.4 was estimated to be 79.31 dimensionless. This BCF value suggests that the test chemical (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one is non bioaccumulative in aquatic organisms.

 

From CompTox Chemistry Dashboard using OPERA (OPEn (quantitative) structure-activity Relationship Application)  V1.02 model in which calculation based on PaDEL descriptors (calculate molecular descriptors and fingerprints of chemical)  the bioaccumulation i.e BCF for test substance(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one(CAS no.2244 -16 -8) was estimated to be 4.53 dimensionless . The predicted BCF result was based on the 5 OECD principles.

 

The supporting weight of evidence study was done from authoritative database (HSDB, 2017) in this study the BCF value of read across chemical (5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS no. 99-49-0) estimated was 30 dimensionless by using log Kow of 3.07 and regression derived equation and it is far less than 2000 criteria so it is concluded that read across chemical (5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one is non bioaccumulative.

 

Last weight of evidence study was also experimental study done from same authoritative database (HSDB, 2017) as mentioned above in this study the BCF value of read across chemical 1,1,3-Trimethyl-3-cyclohexene-5-one ( CAS no. 78-59-1) estimated was 7.0 dimensionless in bluegill sunfish and it is far less than 2000 so it is concluded that this read across chemical is non bioaccumulative.

 

On the basis of above results for target chemical (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS No. 2244-16-8)(from EPI suite, ACD labs, Sci Finder database, Chemspider and CompTox Chemistry Dashboard 2017) and for its structurally similar read across chemicals (From HSDB) it can be concluded that the BCF value of test substance(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-oneranges from 4.53 to 79.31 dimensionless which does not exceed the bioconcentration threshold of 2000, indicating that the chemical(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-oneis expected to be nonbioaccumulative in the food chain.