Methyl ricinoleate

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

experimental study

Adequacy of study:

key study

Study period:

09 May- 6 Jun 1988

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

guideline study with acceptable restrictions

Qualifier:

according to guideline

Guideline:

other: BODIS Test, according to ISO/DIS 10708 (based on the OECD301D Closed Bottle Test and the RDA-Blok-test, previously published (Blok, 1979. "A Repetitive Die Away (RDA) test combining several biodegradability test procedures". Int.Biodeterior.Bull. 15,57-63

Qualifier:

equivalent or similar to guideline

Guideline:

OECD Guideline 301 D (Ready Biodegradability: Closed Bottle Test)

GLP compliance:

no

Oxygen conditions:

aerobic

Inoculum or test system:

activated sludge, domestic, non-adapted

Details on inoculum:

- Source of inoculum/activated sludge: The activated sludge was collected from a sewage treatment plant (Hochdahl), treating predominantly municipal sewage serving for a population equivalent of ca. 27000.

Duration of test (contact time):

28 d

Initial conc.:

100 mg/L

Based on:

ThOD

Parameter followed for biodegradation estimation:

O2 consumption

Details on study design:

TEST CONDITIONS- Composition of medium: According to OECD guideline- Test temperature: 20- 25 °C- Aeration of dilution water: yes, up to 9 mg O2/LTEST SYSTEM- Culturing apparatus: 300 mL bottles- Number of culture flasks/concentration: 3- Method used to create aerobic conditions: the bottles were aerated with compressed air by means of a sintered glass tube until O2 saturation was reached SAMPLING- Sampling frequency: samples were collected on days 7, 14, 21 and 28CONTROL AND BLANK SYSTEM- Inoculum blank: 1

Reference substance:

benzoic acid, sodium salt

Key result

Parameter:

% degradation (O2 consumption)

Value:

87

Sampling time:

28 d

Details on results:

The test substance reached 87% biodegradation after 28 days, meeting the 10-d window criterion. Therefore, it can be considered readily biodegradable.

Results with reference substance:

Sodium acetate reached 86% biodegradation within 14 days.

Table 1: Biodegradation in % calculated on the basis of ThOD (reference substance) and COD (test substance)

Day	Test substance	Reference substance
7	62	75
14	77	86
21	81	89
28	87	94

Validity criteria fulfilled:

yes

Interpretation of results:

readily biodegradable

Reference 2

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

experimental study

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

study well documented, meets generally accepted scientific principles, acceptable for assessment

Qualifier:

according to guideline

Guideline:

other: EPA-560/6-82-003 (PB82-233008) adopted in 1982

Deviations:

no

Qualifier:

equivalent or similar to guideline

Guideline:

OECD Guideline 301 B (Ready Biodegradability: CO2 Evolution Test)

Deviations:

yes

Remarks:

adapted inoculum was used

GLP compliance:

no

Oxygen conditions:

aerobic

Inoculum or test system:

sewage, domestic, adapted

Details on inoculum:

- Pretreatment: Inoculum: 1000 ml DIW dissolves 1 g of organic matter rich soil, 2 mL of activated (aerated) sewage mixed liquor, 50 mL of raw domestic sewage water, 25 mg/L of Difco vitamin-free casamino acids, 25 mg/L of yeast extract and 1 mL of each medium stock solution (1 -3). Test substance were added at concentrations equivalent to 4,8, and 8 mg carbon/L by calculation on days 0, 7, 11, respectively. At day 14, the inoculum was filtered through glass wool.

Duration of test (contact time):

28 d

Initial conc.:

10 mg/L

Based on:

other: TOC

Parameter followed for biodegradation estimation:

CO2 evolution

Details on study design:

TEST CONDITIONS- Composition of medium: Stock solution 1: 35 g/L NH4Cl, 15 g/L KNO3, 75 g/L K2HPO4.3H2O, 25 g/L Na2HPO4.H2O; Stock solution 2: 10 g/L KCl, 20 g/L MgSO4/FeSO4.7H2O; Stock solution 3: 5 g/L CaCl2, 0.05 g/L ZnCl2, 0.5 g/L MnCl2.4H2O, 0.05 g/L CuCl2, 0.001 g/L CoCl2, 0.001 g/L H2BO3, 0.0004 g/L MoO2- Additional substrate: Difco vitamin-free caamino acids, yeast extract- Test temperature: not specified- Continuous darkness: yes- Other: The test vessels were stirred throughout the test.TEST SYSTEM- Culturing apparatus: 2L Erlenmeyer flask contasining 1 L test solution- Number of culture flasks/concentration: not specified- Method used to create aerobic conditions: After inoculation, the test flasks are sparged with CO2 free air.- Measuring equipment: Titration method- Details of trap for CO2 and volatile organics if used: A reservoir holding 10 mL of barium hydroxide solution is suspended in the flask to trap CO2. SAMPLING- Sampling frequency/method: On day 0, 7, 14 and 21, 10 mL of Ba(OH)2 plus 10 mL rinsing water (DIW) were removed for CO2 measurement by titration with 0.1 N HCl to the phenolphthalein end point. The reservoir is refilled with fresh Ba(OH)2. 3 mL of 20% H2SO4, are added on the day prior to terminating the test.

Reference substance:

other: Phillips 2-D reference fuel

Key result

Parameter:

% degradation (CO2 evolution)

Value:

88.49

Sampling time:

28 d

Remarks on result:

other: Rape methyl ester

Key result

Parameter:

% degradation (CO2 evolution)

Value:

85.54

Sampling time:

28 d

Remarks on result:

other: Soyate methyl ester

Details on results:

Rape methyl ester:7d: 66.32%14d: 80.72%Soyate methyl ester:7d: 68.4%14d: 77.83%

Validity criteria fulfilled:

not specified

Interpretation of results:

inherently biodegradable

Reference 3

Endpoint:

biodegradation in water: screening tests

Type of information:

(Q)SAR

Adequacy of study:

supporting study

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 adequate and reliable documentation / justification

Justification for type of information:

see QMRF in "overall remarks" and the QPRF in "executive summary"

Principles of method if other than guideline:

Calculation based on BIOWIN v4.10, Estimation Programs Interface Suite™ for Microsoft® Windows v 4.10. US EPA, United States Environmental Protection Agency, Washington, DC, USA.

GLP compliance:

no

Oxygen conditions:

aerobic

Inoculum or test system:

activated sludge (adaptation not specified)

Details on results:

For detailed description on the model and its applicability, see "Any other information on materials and methods incl. tables".

BIOWIN v4.10 Results

Biowin1 (Linear Model Prediction): Biodegrades Fast

Biowin2 (Non-Linear Model Prediction): Biodegrades Fast

Biowin3 (Ultimate Biodegradation Timeframe): Days-Weeks

Biowin4 (Primary Biodegradation Timeframe): Days

Biowin5 (MITI Linear Model Prediction): Biodegrades Fast

Biowin6 (MITI Non-Linear Model Prediction): Biodegrades Fast

Biowin7 (Anaerobic Model Prediction): Does Not Biodegrade Fast

Ready Biodegradability Prediction: YES

 

TYPE	NUM	Biowin1 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	1	Linear C4 terminal chain [CCC-CH3]	0.1084	0.2169
Frag	1	Aliphatic alcohol [-OH]	0.1587	0.1587
Frag	1	Ester [-C(=O)-O-C]	0.1742	0.1742
MolWt	*	Molecular Weight Parameter		-0.1488
Const	*	Equation Constant		0.7475
RESULT		Biowin1 (Linear Biodeg Probability)		1.0401

 

TYPE	NUM	Biowin2 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	1	Linear C4 terminal chain [CCC-CH3]	1.8437	1.8437
Frag	1	Aliphatic alcohol [-OH]	1.1178	1.1178
Frag	1	Ester [-C(=O)-O-C]	4.0795	4.0795
MolWt	*	Molecular Weight Parameter		-4.4375
RESULT		Biowin2 (Non-Linear Biodeg Probability)		0.9964

 

TYPE	NUM	Biowin3 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	1	Linear C4 terminal chain [CCC-CH3]	0.2983	0.2983
Frag	1	Aliphatic alcohol [-OH]	0.1600	0.1600
Frag	1	Ester [-C(=O)-O-C]	0.1402	0.1402
MolWt	*	Molecular Weight Parameter		-0.6906
Const	*	Equation Constant		3.1992
RESULT		Biowin3 (Survey Model – Ultimate Biodeg)		3.1071

 

TYPE	NUM	Biowin4 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	1	Linear C4 terminal chain [CCC-CH3]	0.2691	0.2691
Frag	1	Aliphatic alcohol [-OH]	0.1294	0.1294
Frag	1	Ester [-C(=O)-O-C]	0.2290	0.2290
MolWt	*	Molecular Weight Parameter		-0.4509
Const	*	Equation Constant		3.8477
RESULT		Biowin4 (Survey Model - Primary Biodeg)		4.0244

 

TYPE	NUM	Biowin5 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	1	Aliphatic alcohol [-OH]	0.1611	0.1611
Frag	1	Ester [-C(=O)-O-C]	0.3437	0.3437
Frag	2	Methyl [-CH3]	0.0004	0.0008
Frag	13	-CH2- [linear]	0.0494	0.6424
Frag	1	-CH- [linear]	-0.0507	-0.0507
Frag	2	-C=CH [alkenyl hydrogen]	0.0062	0.0124
MolWt	*	Molecular Weight Parameter		-0.9297
Const	*	Equation Constant		0.7121
RESULT		Biowin5 (MITI Linear Biodeg Probability)		0.8923

 

TYPE	NUM	Biowin6 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	1	Aliphatic alcohol [-OH]	1.0041	1.0041
Frag	1	Ester [-C(=O)-O-C]	2.4462	2.4462
Frag	2	Methyl [-CH3]	0.0194	0.0389
Frag	13	-CH2- [linear]	0.4295	5.5834
Frag	1	-CH- [linear]	-0.0998	-0.0998
Frag	2	-C=CH [alkenyl hydrogen]	0.0285	0.0570
MolWt	*	Molecular Weight Parameter		-9.0214
RESULT		Biowin6 (MITI Non-Linear Biodeg Probability)		0.9265

 

Validity criteria fulfilled:

not applicable

Interpretation of results:

readily biodegradable

Executive summary:

QPRF: BIOWIN v4.10

1.	Substance	See “Test material identity”
2.	General information
2.1	Date of QPRF	See “Data Source (Reference)”
2.2	QPRF author and contact details	See “Data Source (Reference)”
3.	Prediction
3.1	Endpoint (OECD Principle 1)	Endpoint				Biodegradability
		Dependent variable				Biodegradability
3.2	Algorithm (OECD Principle 2)	Model or submodel name				BIOWIN
		Model version				v. 4.10
		Reference to QMRF				QMRF: Estimation of Aerobic Biodegradability using BIOWIN v4.10 (EPI Suite v4.11): BIOWIN1 to BIOWIN6 and Ready Biodegradability Prediction
		Predicted value (model result)				See “Results and discussion”
		Input for prediction				- Chemical structure via CAS number or SMILES
		Descriptor values				- Structure fragments - Molecular weight
3.3	Applicability domain (OECD principle 3)	Domains (Appendix D, On-Line BIOWIN User’s Guide):
		1) Molecular weight				See below (Assessment of estimation domain)
		2) Fragments:				See below (Assessment of estimation domain)
3.4	The uncertainty of the prediction (OECD principle 4)	Parameter	BIOWIN model
			1	2	3		4	5	6
		Total correct	264 / 295	275 / 295	167 / 200		165 / 200	485 / 589	488 / 589
		% correct, total	89.5	93.2	83.5		82.5	82.3	82.9
		% correct, fast	97.3 (181 / 186)	97.3 (181 / 186)	93.5 (101 / 108)		84.9 (101 / 119)	79.1 (201 / 254)	80.3 (204 / 254)
3.5	The chemical mechanisms according to the model underpinning the predicted result (OECD principle 5)	The chemical structure influences the biodegradability of the substance. Therefore, chemical fragments were selected having a potential effect on biodegradability. In order to be able to predict the biodegradability probability of substances without these specific fragments, the molecular weight was integrated into the models.

 

References

- US EPA (2012). On-Line BIOWIN User’s Guide.

 

 

Assessment of estimation domain (molecular weight, fragments):

Model:	BIOWIN v4.10
Substance:	9-Octadecenoic acid, 12-hydroxy-, methyl ester, R-(Z) -
CAS-#:	141-24-2
SMILES:	O=C(OC)CCCCCCCC=CCC(O)CCCCCC
Molecular weight (g/mol):	312,50
AppendixD - Fragment Coefficients for Biodegradation Models
BIOWIN1 and BIOWIN2: Linear / Non-Linear Biodegradability
Fragment description	Coefficient			Training set fragment count					No. of instances of each bond found for the current substance
	Linear	Non-linear		Min		Max	No. of compounds in training set containing the fragment		.
Linear C4 terminal chain [CCC-CH3]	0,10843	1,8437		-		3	44		1
Aliphatic alcohol [-OH]	0,15873	1,1178		-		3	34		1
Ester [-C(=O)-O-C]	0,17418	4,0795		-		3	23		1
Molecular Weight	---	---		31,06		697,7			in range
.
BIOWIN3 and BIOWIN4: Ultimate / Primary biodegradability
Fragment description	Coefficient				Training set fragment count				No. of instances of each bond found for the current substance
	Ultimate	Primary			Min	Max		No. of compounds in training set containing the fragment	.
Linear C4 terminal chain [CCC-CH3]	0,29834	0,26907			-	3		26	1
Aliphatic alcohol [-OH]	0,15997	0,12945			-	4		18	1
Ester [-C(=O)-O-C]	0,14021	0,22896			-	4		25	1
Molecular Weight	---	---			53,06	697,65		-	in range
BIOWIN5 and BIOWIN6: MITI Biodegradability Coefficients (Linear / Non-Linear)
Fragment description	Coefficient				Training set fragment count				No. of instances of each bond found for the current substance
	Linear	Non-Linear			Min	Max		No. of compounds in training set containing the fragment	.
Aliphatic alcohol [-OH]	0,161139	1,004147			-	5		74	1
Ester [-C(=O)-O-C]	0,343735	2,446162			-	3		46	1
Methyl [-CH3]	0,000411	0,019428			-	9		295	2
-CH2- [linear]	0,049416	0,429494			-	51		214	13
-CH- [linear]	-0,05067	-0,09977			-	4		63	1
-C=CH [alkenyl hydrogen]	0,006189	0,028514			-	9		68	2
Molecular Weight	---	---			30,02	959,2		-	in range
.
BIOWIN7: Anaerobic Biodegradation Coefficients
Fragment description	Coefficient		Training set fragment count						No. of instances of each bond found for the current substance
			Min			Max		No. of compounds in training set containing the fragment
Linear C4 terminal chain [CCC-CH3]	-0,31772	---	-			3		41	1
Aliphatic alcohol [-OH]	0,132763	---	-			5		27	1
Ester [-C(=O)-O-C]	0,171852	---	-			3		13	1
Methyl [-CH3]	-0,07957	---	-			4		86	2
-CH2- [linear]	0,025989	---	-			44		67	13
-CH- [linear]	-0,16585	---	-			2		17	1
-C=CH [alkenyl hydrogen]	-0,07352	---	-			11		15	2
Molecular Weight	---	---	46,07			885,46			in range

Description of key information

Readily biodegradable: 87% in 28 days (ISO 10708, read across)

Key value for chemical safety assessment

Biodegradation in water:

readily biodegradable

Additional information

Experimental studies investigating the ready biodegradability of Methyl ricinoleate (CAS 141-24-2) are not available. Thus, the biodegradation assesment is based on available data for the structurally similar source substance Fatty acids, C16-18 and C18-unsatd., Me esters (CAS 67762-38-3) in a read across approach as well as supporting experimental and QSAR data.

The key study with Fatty acids, C16-18 and C18-unsatd., Me esters was conducted according to ISO guideline 10708 (BODIS test) under aerobic conditions using non-adapted activated sludge as inoculum (BASF, 2001). An initial test concentration of 100 mg/L (ThOD) was applied. Based on O2 consumption a mean degradation of 87% was observed after 28 days. The 14-day window was passed. Hence, the substance is readily biodegradable according to OECD criteria. Based on the structural similarity this conclusion is also considered to be true for methyl ricinoleate.

This assumption is supported by QSAR calculations using BIOWIN 4.1 (prediction: readily biodegradable) and additional experimental data for soyate and rape methyl ester, which confirm the rapid biodegradability, however using adapted inoculum.