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

Adsorption / desorption

Link to relevant study record(s)

Reference

Endpoint:

adsorption / desorption

Remarks:

adsorption

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 KOCWIN Program (v2.00)

GLP compliance:

not specified

Type of method:

other: MCI Method

Media:

soil

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

Test temperature:

25 deg.C

Analytical monitoring:

not specified

Key result

Type:

Koc

Value:

136.2 L/kg

Temp.:

25 °C

Remarks on result:

other: Log Koc= 2.1341 (estimated by MCI method)

Transformation products:

not specified

KOCWIN Program (v2.00) Results:

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

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

CHEM :

MOL FOR: C10 H14 O1

MOL WT : 150.22

--------------------------- KOCWIN v2.00 Results ---------------------------

Koc Estimate from MCI:

---------------------

First Order Molecular Connectivity Index ........... : 5.109

Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 3.2632

Fragment Correction(s):

1 Ketone (-C-CO-C-) ................... : -1.1290

Corrected Log Koc .................................. : 2.1341

Estimated Koc: 136.2 L/kg <===========

Validity criteria fulfilled:

not specified

Conclusions:

The Soil Adsorption Coefficient i.e. Koc value of test chemical (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS No. 2244-16-8) was estimated using EPI suite KOCWIN Program (v2.00) as 136.2 L/kg (log Koc= 2.1314) by means of MCI method at 25 deg. C. This log Koc value indicates that test chemical (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one has low sorption to soil and therefore test chemical has moderate migration potential to ground water.

Executive summary:

The Soil Adsorption Coefficient i.e. Koc value of test chemical (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS No. 2244-16-8) was estimated using EPI suite KOCWIN Program (v2.00) as 136.2 L/kg (log Koc= 2.1314) by means of MCI method at 25 deg. C.  This log Koc value indicates that test chemical (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one has low sorption to soil and therefore test chemical has moderate migration potential to ground water.

Description of key information

The Soil Adsorption Coefficient i.e. Koc value of test chemical (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS No. 2244-16-8) was estimated using EPI suite KOCWIN Program (v2.00) as 136.2 L/kg (log Koc= 2.1314) by means of MCI method at 25 deg. C.  This log Koc value indicates that test chemical (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one has low sorption to soil and therefore test chemical has moderate migration potential to ground water.

Key value for chemical safety assessment

Koc at 20 °C:

136.2

Additional information

Various predicted data for the target compound of(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 chemicals were reviewed for the Adsorption end point are summarized as below.

In first weight of evidence study the Soil Adsorption Coefficient i.e. Koc value of test chemical (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS No. 2244-16-8) was estimated using Estimation Program Interface (EPI suite, 2017) KOCWIN Program (v2.00) as 136.2 L/kg (log Koc= 2.1314) by means of MCI method at 25 deg. C.  This log Koc value indicates that test chemical (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one has low sorption to soil and therefore test chemical has moderate migration potential to ground water.

 

In next weight of evidence study the Soil Adsorption Coefficient i.e Koc value of test substance (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one(CAS no.2244 -16 -8) was estimated using Adsorption Coefficient module (v12.1.0.50374) program of(ACD (Advanced Chemistry Development)/I-Lab predictive module, 2017) moduleas Koc 407 dimensionless (log Koc= 2.6095). This log Koc value indicates that the test substance (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-onehas a moderate sorption to soil and therefore has slow migration potential to groundwater.

Third weight of evidence study was done by using Sci Finder database of American Chemical Society (ACS, 2017) in this study the soil adsorption co-efficient i.e., Koc value of test chemical (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one was estimated to be 408 dimensionless ( log Koc = 2.6106) at pH 1-10 at temperature 25 deg.c. this value suggests that this test chemical has moderate sorption to soil therefore has slow migration potential to ground water.

 

Another weight of evidence study was done by using Chemspider-ACD/Phy chem suite of Royal Society of Chemistry (RCS, 2017) in this study the soil adsorption co-efficient i.e., Koc value of test substance (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one was estimated to be 796.41 dimensionless (log Koc= 2.9011) at pH 5.5 and 7.4 and temperature 25 deg.C . This Koc value at different pH indicates that the chemical (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one has moderate sorption to soil and sediments and therefore test chemical has slow migration potential to ground water.

 

Next weight of evidence study was done 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 adsorption coefficient i.e KOC 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 226 L/kg (log Koc = 2.3541) .The predicted KOC result based on the 5 OECD principles. Thus based on the result it is concluded that the test substance (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-onehas a low sorption to soil and sediment and therefore has moderate migration potential to ground water.

 

The supporting experimental weight of evidence study was done from authoritative database HSDB, 2017 in this study the Koc value for read across chemical (5R)-2-Methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one (CAS no.99-49-0) was estimated by using a structure estimation method based on molecular connectivity indices. The estimated Koc value was 140 dimensionless and log Koc is 2.1461 this log Koc value suggests that (5R)-2-Methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one is expected to have low sorption to soil and sediment and therefore have moderate migration potential to ground water.

 

Last weight of evidence study was also experimental study done from same authoritative database (HSDB, 2017) in this study the Koc value for read across chemical 1,1,3-Trimethyl-3-cyclohexene-5-one (CAS no.78-59-1) was estimated by using a log Kow of 1.7 and a regression-derived equation. The estimated Koc value is 200 dimensionless and log Koc is 2.3010 this log Koc value suggests that 1,1,3-Trimethyl-3-cyclohexene-5-one is expected to have low sorption to soil and sediment and therefore have moderate migration potential to ground water.

 

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, Comptox chemistry dashboard and Chemspider 2017) and for its read across chemicals (From authoritative database HSDB) it can be concluded that the log Koc value of(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-oneranges from 2.1341 to 2.9011 indicating that the chemical(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (CAS No. 2244-16-8)has low to moderate sorption to soil and sediment and therefore it has moderate to slow migration potential to ground water.

[LogKoc: 2.1314]