2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

calculation (if not (Q)SAR)

Remarks:

Migrated phrase: estimated by calculation

Adequacy of study:

key study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Estimated data generated using the EPI Suite model developed by the USEPA

Qualifier:

according to guideline

Guideline:

other: Modelling database

Principles of method if other than guideline:

BIOWIN estimates the probability of rapid aerobic and anaerobic biodegradation of an organic compound in the presence of mixed populations of environmental microorganisms. BIOWIN contains seven separate models. This version (v4.10) designates the models as follows (see also Boethling et al. 2003):
Biowin1 = linear probability model
Biowin2 = nonlinear probability model
Biowin3 = expert survey ultimate biodegradation model
Biowin4 = expert survey primary biodegradation model
Biowin5 = MITI linear model
Biowin6 = MITI nonlinear model
Biowin7 = anaerobic biodegradation model
Biodegradability estimates are based upon fragment constants that were developed using multiple linear or non-linear regression analyses, depending on the model.

GLP compliance:

not specified

Oxygen conditions:

other: aerobic (Biowin 1-6) and anaerobic (Biowin 7)

Inoculum or test system:

other: mixed populations of environmental microorganisms

Duration of test (contact time):

2.718 wk

Details on study design:

Using the computer tool BIOWIN v4.10 by US-EPA (EPIWIN) the aerobic as well as the anaerobic biodegradability of the test material can be estimated. The follwoing seven different models are used by the tool: Linear Model, Non-Linear Model, Ultimate Biodegradation Timeframe, Primary Biodegradation Timeframe, MITI LInear Model, MITI Non-Linear Model and Anaerobic Model (calles Biowin 1-7, respectively). Due to this results the overall prediction of readily biodegradability is done for the desired chemical.

Parameter:

other: Half-life

Value:

50

Sampling time:

2.718 wk

Remarks on result:

other: Other details not known

Details on results:

Biowin1 (Linear Model Prediction) : 0.6298: Biodegrades Fast
Biowin2 (Non-Linear Model Prediction): 0.4119: Does Not Biodegrade Fast
Biowin3 (Ultimate Biodegradation Timeframe): 2.7176: Weeks-Months
Biowin4 (Primary Biodegradation Timeframe): 3.5434: Days-Weeks
Biowin5 (MITI Linear Model Prediction) : 0.5078: Biodegrades Fast
Biowin6 (MITI Non-Linear Model Prediction): 0.3589: Does Not Biodegrade Fast
Biowin7 (Anaerobic Model Prediction): 0.1407: Does Not Biodegrade Fast
Ready Biodegradability Prediction: NO

BIOWIN (v4.10) Program Results:

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

SMILES : OCC(=CCC(C(C(=C1)C)(C)C)C1)C

CHEM : 2-Buten-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-

MOL FOR: C13 H22 O1

MOL WT : 194.32

--------------------------- BIOWIN v4.10 Results ----------------------------

Biowin1 (Linear Model Prediction) : Biodegrades Fast

Biowin2 (Non-Linear Model Prediction): Does Not Biodegrade Fast

Biowin3 (Ultimate Biodegradation Timeframe): Weeks-Months

Biowin4 (Primary Biodegradation Timeframe): Days-Weeks

Biowin5 (MITI Linear Model Prediction) : Biodegrades Fast

Biowin6 (MITI Non-Linear Model Prediction): Does Not Biodegrade Fast

Biowin7 (Anaerobic Model Prediction): Does Not Biodegrade Fast

Ready Biodegradability Prediction: NO

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin1 FRAGMENT DESCRIPTION | COEFF | VALUE

------+-----+--------------------------------------------+---------+---------

Frag | 1 | Aliphatic alcohol [-OH] | 0.1587 | 0.1587

Frag | 1 | Carbon with 4 single bonds & no hydrogens | -0.1839 | -0.1839

MolWt| * | Molecular Weight Parameter | | -0.0925

Const| * | Equation Constant | | 0.7475

============+============================================+=========+=========

RESULT | Biowin1 (Linear Biodeg Probability) | | 0.6298

============+============================================+=========+=========

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin2 FRAGMENT DESCRIPTION | COEFF | VALUE

------+-----+--------------------------------------------+---------+---------

Frag | 1 | Aliphatic alcohol [-OH] | 1.1178 | 1.1178

Frag | 1 | Carbon with 4 single bonds & no hydrogens | -1.7232 | -1.7232

MolWt| * | Molecular Weight Parameter | | -2.7593

============+============================================+=========+=========

RESULT | Biowin2 (Non-Linear Biodeg Probability) | | 0.4119

============+============================================+=========+=========

A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast

A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin3 FRAGMENT DESCRIPTION | COEFF | VALUE

------+-----+--------------------------------------------+---------+---------

Frag | 1 | Aliphatic alcohol [-OH] | 0.1600 | 0.1600

Frag | 1 | Carbon with 4 single bonds & no hydrogens | -0.2121 | -0.2121

MolWt| * | Molecular Weight Parameter | | -0.4294

Const| * | Equation Constant | | 3.1992

============+============================================+=========+=========

RESULT | Biowin3 (Survey Model - Ultimate Biodeg) | | 2.7176

============+============================================+=========+=========

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin4 FRAGMENT DESCRIPTION | COEFF | VALUE

------+-----+--------------------------------------------+---------+---------

Frag | 1 | Aliphatic alcohol [-OH] | 0.1294 | 0.1294

Frag | 1 | Carbon with 4 single bonds & no hydrogens | -0.1534 | -0.1534

MolWt| * | Molecular Weight Parameter | | -0.2804

Const| * | Equation Constant | | 3.8477

============+============================================+=========+=========

RESULT | Biowin4 (Survey Model - Primary Biodeg) | | 3.5434

============+============================================+=========+=========

Result Classification: 5.00 -> hours 4.00 -> days 3.00 -> weeks

(Primary & Ultimate) 2.00 -> months 1.00 -> longer

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin5 FRAGMENT DESCRIPTION | COEFF | VALUE

------+-----+--------------------------------------------+---------+---------

Frag | 1 | Aliphatic alcohol [-OH] | 0.1611 | 0.1611

Frag | 1 | Carbon with 4 single bonds & no hydrogens | 0.0676 | 0.0676

Frag | 4 | Methyl [-CH3] | 0.0004 | 0.0016

Frag | 2 | -CH2- [linear] | 0.0494 | 0.0988

Frag | 1 | -CH2- [cyclic] | 0.0197 | 0.0197

Frag | 1 | -CH - [cyclic] | 0.0124 | 0.0124

Frag | 2 | -C=CH [alkenyl hydrogen] | 0.0062 | 0.0124

MolWt| * | Molecular Weight Parameter | | -0.5781

Const| * | Equation Constant | | 0.7121

============+============================================+=========+=========

RESULT | Biowin5 (MITI Linear Biodeg Probability) | | 0.5078

============+============================================+=========+=========

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin6 FRAGMENT DESCRIPTION | COEFF | VALUE

------+-----+--------------------------------------------+---------+---------

Frag | 1 | Aliphatic alcohol [-OH] | 1.0041 | 1.0041

Frag | 1 | Carbon with 4 single bonds & no hydrogens | 0.3990 | 0.3990

Frag | 4 | Methyl [-CH3] | 0.0194 | 0.0777

Frag | 2 | -CH2- [linear] | 0.4295 | 0.8590

Frag | 1 | -CH2- [cyclic] | 0.2365 | 0.2365

Frag | 1 | -CH - [cyclic] | -0.1295 | -0.1295

Frag | 2 | -C=CH [alkenyl hydrogen] | 0.0285 | 0.0570

MolWt| * | Molecular Weight Parameter | | -5.6098

============+============================================+=========+=========

RESULT |Biowin6 (MITI Non-Linear Biodeg Probability)| | 0.3589

============+============================================+=========+=========

A Probability Greater Than or Equal to 0.5 indicates --> Readily Degradable

A Probability Less Than 0.5 indicates --> NOT Readily Degradable

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin7 FRAGMENT DESCRIPTION | COEFF | VALUE

------+-----+--------------------------------------------+---------+---------

Frag | 1 | Aliphatic alcohol [-OH] | 0.1328 | 0.1328

Frag | 1 | Carbon with 4 single bonds & no hydrogens | -0.3342 | -0.3342

Frag | 4 | Methyl [-CH3] | -0.0796 | -0.3183

Frag | 2 | -CH2- [linear] | 0.0260 | 0.0520

Frag | 1 | -CH2- [cyclic] | -0.1200 | -0.1200

Frag | 1 | -CH - [cyclic] | 0.0395 | 0.0395

Frag | 2 | -C=CH [alkenyl hydrogen] | -0.0735 | -0.1470

Const| * | Equation Constant | | 0.8361

============+============================================+=========+=========

RESULT | Biowin7 (Anaerobic Linear Biodeg Prob) | | 0.1407

============+============================================+=========+=========

A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast

A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast

Ready Biodegradability Prediction: (YES or NO)

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

Criteria for the YES or NO prediction: If the Biowin3 (ultimate survey

model) result is "weeks" or faster (i.e. "days", "days to weeks", or

"weeks" AND the Biowin5 (MITI linear model) probability is >= 0.5, then

the prediction is YES (readily biodegradable). If this condition is not

satisfied, the prediction is NO (not readily biodegradable). This method

is based on application of Bayesian analysis to ready biodegradation data

(see Help). Biowin5 and 6 also predict ready biodegradability, but for

degradation in the OECD301C test only; using data from the Chemicals

Evaluation and Research Institute Japan (CERIJ) database.

Validity criteria fulfilled:

not specified

Interpretation of results:

under test conditions no biodegradation observed

Conclusions:

The screening test ready biodegradability of the substance was calculated using the software BIOWIN v4.10.
The results indicate that 2-Buten-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)- is not expected to be readily biodegradable.

Executive summary:

Estimation Programs Interface Suite (EPI suite, 2016) was run to predict the biodegradation potential of the test compound 2-Buten-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)- (CAS no. 28219 -60 -5). The screening tests ready biodegradability of the test substance was calculated using the software BIOWIN v4.10. The results indicate that 2-Buten-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)- is not expected to

be readily biodegradable in nature.

Description of key information

Estimation Programs Interface Suite (EPI suite, 2016) was run to predict the biodegradation potential of the test compound 2-Buten-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)- (CAS no. 28219 -60 -5). The screening tests ready biodegradability of the test substance was calculated using the software BIOWIN v4.10. The results indicate that 2-Buten-1-ol, 2-methyl-4-(2,2,3-trimethyl-3 cyclopenten-1-yl)- is not expected to be readily biodegradable in nature.

Key value for chemical safety assessment

Biodegradation in water:

under test conditions no biodegradation observed

Additional information

Predicted data for the test compound2-Buten-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-(CAS No. 28219-60-5) and the study for its read across substance were reviewed for the biodegradation end point which are summarized as below:

 

Estimation Programs Interface Suite (EPI suite, 2016) was run to predict the biodegradation potential of the test compound 2-Buten-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)- (CAS no. 28219 -60 -5). The screening tests ready biodegradability of the test substance was calculated using the software BIOWIN v4.10. The results indicate that 2-Buten-1-ol, 2-methyl-4-(2,2,3-trimethyl-3 cyclopenten-1-yl)- is not expected to be readily biodegradable in nature.

 

Biodegradation study was conducted for 10 days for evaluating the percentage biodegradability of test substance Terpineol (A. D. READ and R. M. MANSER, 1976). Test chemical concentration used in the study were1, 2, 5 and 10 mg/l expressed as TOC. Solutions of test chemical were diluted to the required concentrations with oxygen- saturated water and then inoculated with domestic sewage at the beginning of the test period. The BOD5 and BOD10 value was determined to be 0.4 and 1.5 mg/l oxygen consumption/g test material. Thus, the substance Terpineol is not considered to be readily biodegradable in water.

Biodegradation study was conducted (A. J. FRANCIS et. al; 1980) for 30 days for evaluating the percentage biodegradability of test substance alpha-Terpineol. Mixed bacterial culture was used as a test inoculum and the study was performed under anaerobic conditions and at a temp. of 28ᵒC. Inoculum was isolated from Leachate samples collected from trenches 26 and 32 from Maxey Flats, Ky., were filter sterilized. Initial test substance conc. used in the study was0.16 and 0.26 mg/l, respectively. A mixed culture of bacteria isolated from each of the two trenches was used to inoculate 100 ml of the respective filter-sterilized trench waters in serum bottles filled with N2. Uninoculated, filter sterilized control samples were incubated under identical conditions. After 30 days of incubation at 28°C, the inoculated and the control samples were analysed for the organic constituents by gas chromatography and mass spectrometry. The percentage degradation of the test chemical was determined to be -6 and -12% by GC-MS parameter in 30 days. Thus, the substance alpha-Terpineol is not considered to be readily biodegradable in water.

Biodegradation study was conducted (A. J. Francis, 1980) for 21 days for evaluating the percentage biodegradability of test substance alpha-Terpineol.Mixed bacterial culture was used as a test inoculum and the study was performed under aerobic conditions and at a temp. of 28ᵒC. Inoculum was isolated from Leachate samples collected from Maxey Flats trench 19S.Sterile mineral salt medium was used for the study. Alpha-terpineol, 0.04% vol/vol or wt/vol, was separately added to 50 ml of sterile mineral salts medium in biometer flasks. This sample was inoculated with 0.2 ml of mixed bacterial culture obtained from Maxey Flats 19S leachate. All samples, in duplicate, were incubated under aerobic conditions at room temperature. The carbon dioxide produced by these samples was absorbed by the alkali and determined volumetrically on a periodic basis. Aerobic samples were incubated in 500-ml sterilized Erlenmeyer flasks fitted with cotton plugs on a rotary shaker at 28°C for 21 days. No degradation of the test chemical was determined by CO2 production parameter in 21 days. Thus, the substance alpha-Terpineolis not considered to be readily biodegradable in water.

On the basis of above results for target and read across substance, it can be concluded that the test substance2-Buten-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-can be expected to be not readily biodegradable in nature.