Butyl O-acetylricinoleate

Toxicity to aquatic algae and cyanobacteria

Link to relevant study record(s)

Reference

Endpoint:

toxicity to aquatic algae and cyanobacteria

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:

The supporting QMRF report has been attached

Qualifier:

according to guideline

Guideline:

other: as mentioned below

Principles of method if other than guideline:

The data is predicted using the OECD QSAR toolbox version 3.4 with logKow as the primary descriptor.

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material (as cited in study report): butyl 12-acetoxyoctadec-9-enoate
- Molecular formula : C24H44O4
- Molecular weight : 396.6076 g/mol
- Smiles notation : CCCCCC[C@H](C\C=C/CCCCCCCC(=O)OCCCC)OC(=O)C
- InChl : 1S/C24H44O4/c1-4-6-8-15-18-23(28-22(3)25)19-16-13-11-9-10-12-14-17-20-24(26)27-21-7-5-2/h13,16,23H,4-12,14-15,17-21H2,1-3H3/b16-13-/t23-/m1/s1
- Substance type:Organic
- Physical state:Liquid

Analytical monitoring:

not specified

Vehicle:

not specified

Test organisms (species):

Pseudokirchneriella subcapitata (previous names: Raphidocelis subcapitata, Selenastrum capricornutum)

Test type:

static

Water media type:

freshwater

Total exposure duration:

72 h

Hardness:

0.24 mmol/L (= 24 mg/L) as CaCO3.

Test temperature:

23 - 25 °C

pH:

at the start of test - 8.1
at the end of test - 9.5-9.6

Key result

Duration:

72 h

Dose descriptor:

EC50

Effect conc.:

45.016 mg/L

Nominal / measured:

estimated

Conc. based on:

test mat.

Basis for effect:

growth rate

The prediction was based on dataset comprised from the following descriptors: EC50
Estimation method: Takes average value from the 8 nearest neighbours
Domain  logical expression:Result: In Domain

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

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Acetoxy AND Alkene AND Allyl AND Carboxylic acid ester by Organic Functional groups

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Allyl AND Carboxylic acid ester AND Overlapping groups by Organic Functional groups (nested)

Domain logical expression index: "c"

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

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Carbonic acid derivative AND Carboxylic acid derivative AND Carboxylic acid ester by Organic functional groups, Norbert Haider (checkmol)

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as No alert found by DNA binding by OECD

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as Acylation OR Acylation >> Isocyanates and Isothiocyanates OR Acylation >> Isocyanates and Isothiocyanates >> Isocyanates OR Acylation >> P450 Mediated Activation to Isocyanates or Isothiocyanates OR Acylation >> P450 Mediated Activation to Isocyanates or Isothiocyanates >> Benzylamines-Acylation OR Michael addition OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Alkyl phenols OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Arenes OR Michael addition >> Polarised Alkenes-Michael addition OR Michael addition >> Polarised Alkenes-Michael addition >> Alpha, beta- unsaturated aldehydes OR Michael addition >> Polarised Alkenes-Michael addition >> Alpha, beta- unsaturated esters OR Michael addition >> Polarised Alkenes-Michael addition >> Alpha, beta- unsaturated ketones OR Schiff base formers OR Schiff base formers >> Direct Acting Schiff Base Formers OR Schiff base formers >> Direct Acting Schiff Base Formers >> Mono aldehydes OR SN1 OR SN1 >> Carbenium Ion Formation OR SN1 >> Carbenium Ion Formation >> Alpha halo ethers (including alpha halo thioethers) OR SN1 >> Iminium Ion Formation OR SN1 >> Iminium Ion Formation >> Aliphatic tertiary amines OR SN1 >> Nitrenium Ion formation OR SN1 >> Nitrenium Ion formation >> Aromatic nitro OR SN1 >> Nitrenium Ion formation >> Primary (unsaturated) heterocyclic amine OR SN1 >> Nitrenium Ion formation >> Primary aromatic amine OR SN2 OR SN2 >> Direct Acting Epoxides and related OR SN2 >> Direct Acting Epoxides and related >> Epoxides OR SN2 >> SN2 at an sp3 Carbon atom OR SN2 >> SN2 at an sp3 Carbon atom >> Phosphonic esters by DNA binding by OECD

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as No alert found by Protein binding by OASIS v1.4

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Acylation OR Acylation >> Acylation involving an activated (glucuronidated) carboxamide group OR Acylation >> Acylation involving an activated (glucuronidated) carboxamide group >> Carboxylic Acid Amides OR Acylation >> Acylation involving an activated (glucuronidated) ester group OR Acylation >> Acylation involving an activated (glucuronidated) ester group >> Arenecarboxylic Acid Esters OR Acylation >> Direct acylation involving a leaving group OR Acylation >> Direct acylation involving a leaving group >> Carbamates  OR Acylation >> Direct acylation involving a leaving group >> Carboxylic Acid Amides OR Acylation >> Ester aminolysis OR Acylation >> Ester aminolysis >> Amides OR Acylation >> Ester aminolysis or thiolysis OR Acylation >> Ester aminolysis or thiolysis >> Activated aryl esters  OR Acylation >> Ester aminolysis or thiolysis >> Carbamates  OR Acylation >> Ring opening acylation OR Acylation >> Ring opening acylation >> Active cyclic agents  OR AN2 OR AN2 >> Michael addition to activated double bonds OR AN2 >> Michael addition to activated double bonds >> alpha,beta-Unsaturated Carbonyls and Related Compounds OR AN2 >> Michael addition to alpha, beta-unsaturated acids and esters OR AN2 >> Michael addition to alpha, beta-unsaturated acids and esters >> alpha,beta-Unsaturated Carboxylic Acids and Esters OR AN2 >> Michael-type addition to quinoid structures  OR AN2 >> Michael-type addition to quinoid structures  >> Carboxylic Acid Amides OR AN2 >> Michael-type addition to quinoid structures  >> Substituted Phenols OR AN2 >> Nucleophilic addition to pyridonimine tautomer of aminopyridoindoles or aminopyridoimidazoles (hypothesized) OR AN2 >> Nucleophilic addition to pyridonimine tautomer of aminopyridoindoles or aminopyridoimidazoles (hypothesized) >> Heterocyclic Aromatic Amines OR Michael addition OR Michael addition >> Michael addition on conjugated systems with electron withdrawing group OR Michael addition >> Michael addition on conjugated systems with electron withdrawing group >> alpha,beta-Carbonyl compounds with polarized double bonds  OR Michael addition >> Michael addition on conjugated systems with electron withdrawing group >> Conjugated systems with electron withdrawing groups  OR Nucleophilic addition OR Nucleophilic addition >> Addition to carbon-hetero double bonds OR Nucleophilic addition >> Addition to carbon-hetero double bonds >> Ketones OR Radical reactions OR Radical reactions >> ROS Generation OR Radical reactions >> ROS Generation >> Sterically Hindered Piperidine Derivatives OR Radical reactions >> ROS generation and direct attack of hydroxyl radical to the C8 position of nucleoside base OR Radical reactions >> ROS generation and direct attack of hydroxyl radical to the C8 position of nucleoside base >> Heterocyclic Aromatic Amines OR Schiff base formation OR Schiff base formation >> Direct acting Schiff base formers OR Schiff base formation >> Direct acting Schiff base formers >> 1,2-Dicarbonyls and 1,3-Dicarbonyls  OR SE reaction (CYP450-activated heterocyclic amines) OR SE reaction (CYP450-activated heterocyclic amines) >> Direct attack of arylnitrenium cation to the C8 position of nucleoside base  OR SE reaction (CYP450-activated heterocyclic amines) >> Direct attack of arylnitrenium cation to the C8 position of nucleoside base  >> Heterocyclic Aromatic Amines OR SN2 OR SN2 >> Interchange reaction with sulphur containing compounds OR SN2 >> Interchange reaction with sulphur containing compounds >> Thiols and disulfide compounds  OR SN2 >> Nucleophilic substitution at sp3 carbon atom OR SN2 >> Nucleophilic substitution at sp3 carbon atom >> Alkyl halides  OR SN2 >> Nucleophilic substitution at sp3 carbon atom >> alpha-Activated haloalkanes  OR SN2 >> Nucleophilic substitution at sp3 carbon atom >> Phosphonates OR SN2 >> Nucleophilic substitution on benzilyc carbon atom OR SN2 >> Nucleophilic substitution on benzilyc carbon atom >> alpha-Activated benzyls  OR SN2 >> Protein and/or DNA alkylation OR SN2 >> Protein and/or DNA alkylation >> Dialkyl Alkylphosphonates OR SN2 >> SN2 Reaction at a sp3 carbon atom OR SN2 >> SN2 Reaction at a sp3 carbon atom >> Activated alkyl esters and thioesters  OR SNAr OR SNAr >> Nucleophilic aromatic substitution on activated aryl and heteroaryl compounds OR SNAr >> Nucleophilic aromatic substitution on activated aryl and heteroaryl compounds >> Activated aryl and heteroaryl compounds OR SR reaction (peroxidase-activated heterocyclic amines) OR SR reaction (peroxidase-activated heterocyclic amines) >> Direct attack of arylnitrenium radical to the C8 position of nucleoside base OR SR reaction (peroxidase-activated heterocyclic amines) >> Direct attack of arylnitrenium radical to the C8 position of nucleoside base >> Heterocyclic Aromatic Amines by Protein binding by OASIS v1.4

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as No alert found by Protein binding by OECD

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Acylation OR Acylation >> Direct Acylation Involving a Leaving group OR Acylation >> Direct Acylation Involving a Leaving group >> Acetates OR SN2 OR SN2 >> SN2 reaction at sp3 carbon atom OR SN2 >> SN2 reaction at sp3 carbon atom >> Allyl acetates and related chemicals OR SNAr OR SNAr >> Nucleophilic aromatic substitution OR SNAr >> Nucleophilic aromatic substitution >> Activated halo-benzenes by Protein binding by OECD

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as Class 5 (Not possible to classify according to these rules) by Acute aquatic toxicity classification by Verhaar (Modified) ONLY

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Not bioavailable by Lipinski Rule Oasis ONLY

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Group 14 - Carbon C AND Group 16 - Oxygen O by Chemical elements

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as Group 1 - Alkali Earth Li,Na,K,Rb,Cs,Fr OR Group 15 - Nitrogen N OR Group 16 - Sulfur S OR Group 17 - Halogens Cl OR Group 17 - Halogens F OR Group 17 - Halogens F,Cl,Br,I,At by Chemical elements

Domain logical expression index: "o"

Referential boundary: The target chemical should be classified as No alert found by rtER Expert System ver.1 - USEPA

Domain logical expression index: "p"

Referential boundary: The target chemical should be classified as Parabens by rtER Expert System ver.1 - USEPA

Domain logical expression index: "q"

Referential boundary: The target chemical should be classified as Not known precedent reproductive and developmental toxic potential by DART scheme v.1.0

Domain logical expression index: "r"

Referential boundary: The target chemical should be classified as Di-carboxylic acid derivatives (adipates) (22d) OR Known precedent reproductive and developmental toxic potential by DART scheme v.1.0

Domain logical expression index: "s"

Referential boundary: The target chemical should be classified as days - weeks by Biodeg ultimate (Biowin 3) ONLY

Domain logical expression index: "t"

Parametric boundary:The target chemical should have a value of log Kow which is >= 6.26

Domain logical expression index: "u"

Parametric boundary:The target chemical should have a value of log Kow which is <= 11.4

Validity criteria fulfilled:

not specified

Conclusions:

The median Effective concentration (EC50) value for butyl 12-acetoxyoctadec-9-enoate on Pseudokirchneriella subcapitata in a 72 hour study was estimated to be 45 mg/L on the basis of effects on growth rate.

Executive summary:

Based on the prediction done using the OECD QSAR toolbox version 3.4 with log kow as the primary descriptor and considering the five closest read across substances, the short term toxicity on aquatic algae and cyanobacteria was predicted for target substance butyl 12-acetoxyoctadec-9-enoate (CAS no. 140 -04 -5). EC50 value was estimated to be 45mg/l for Pseudokirchneriella subcapitata for 72 h duration on the basis of effects on growth rate. Based on this value it can be concluded that the substance butyl 12-acetoxyoctadec-9-enoate is considered to be toxic to aquatic organisms Since the test chemical is readily biodegradable in nature, chemical butyl 12-acetoxyoctadec-9-enoate can be considered to be non-toxic to aquatic environment and can be considered to be not classified as per the CLP classification criteria.

 

Description of key information

Based on the prediction done using the OECD QSAR toolbox version 3.4 with log kow as the primary descriptor and considering the five closest read across substances, the short term toxicity on aquatic algae and cyanobacteria was predicted for target substance butyl 12-acetoxyoctadec-9-enoate (CAS no. 140 -04 -5). EC50 value was estimated to be 45mg/l for Pseudokirchneriella subcapitata for 72 h duration on the basis of effects on growth rate. Based on this value it can be concluded that the substance butyl 12-acetoxyoctadec-9-enoate is considered to be toxic to aquatic organisms Since the test chemical is readily biodegradable in nature, chemical butyl 12-acetoxyoctadec-9-enoate can be considered to be non-toxic to aquatic environment and can be considered to be not classified as per the CLP classification criteria.

 

Key value for chemical safety assessment

EC50 for freshwater algae:

45 mg/L

Additional information

1 predicted data for the target chemical butyl 12-acetoxyoctadec-9-enoate (CAS no. 140-04-5) which is supported further by total 2 weight of evidence studies (from authoritative database and secondary source) for its closest read across substance with logKow as the primary descriptor were reviewed for the toxicity to aquatic algae and cyanobacteria end point which are summarized as below:

 

Short term toxicity on aquatic algae and cyanobacteria of target chemical butyl 12-acetoxyoctadec-9-enoate (CAS no. 140 -04 -5) is predicted using the OECD QSAR toolbox version 3.4 with log kow as the primary descriptor and considering the five closest read across substances (2017). EC50 value was estimated to be 45mg/l for Pseudokirchneriella subcapitata for 72 h duration on the basis of effects on growth rate. Based on this value it can be concluded that the substance butyl 12-acetoxyoctadec-9-enoate is considered to be toxic to aquatic organisms. Since the test chemical is readily biodegradable in nature, chemical butyl 12-acetoxyoctadec-9-enoate can be considered to be non-toxic to aquatic environment and can be considered to be not classified as per the CLP classification criteria.

 

In a supporting study of read across chemical Bis (2 -ethylhexyl) adipate (CAS no. 103 -23 -1)from authoritative database (J-CHECK, 2016), short term toxicity to green algae study was carried out for 72 hrs. The study was performed according to OECD Guideline 201 (Alga, Growth Inhibition Test). The study was based on the effects of the read across compound Bis (2 -ethylhexyl) adipate (CAS no. 103 -23 -1) on green algae in a static fresh water system. Based on effect on growth rate and AUG of the test organism green algae, the 72 hr EC50 and NOEC value was determined to be > 50 and 50 mg/l, respectively. Thus, based on the EC50 value, it can be concluded that the substance Bis (2 -ethylhexyl) adipate is considered to be toxic to aquatic organisms. Since the test chemical is readily biodegradable in nature, chemical Bis (2 -ethylhexyl) adipate can be considered to be non-toxic to aquatic environment and can be considered to be not classified as per the CLP classification criteria.

 

For another read across chemical Dibutyl adipate (CAS no. 105 -99 -7), short term toxicity to Selenastrum capricornutum (algae) study was carried out for 72 hrs according to OECD Guideline 201 (Alga, Growth Inhibition Test) (OECD SIDS Initial Assessment Report, 1996). The study was performed. The study was based on the effects of the read across compound Dibutyl adipate (CAS no. 105 -99 -7) on Selenastrum capricornutum in a static fresh water system. Selenastrum capricornutum ATCC 22662 was used as test organism. Analytical monitoring was not done. 5 nominal concentrations (1 -5 mg/l) of test chemical was used in the study. Stock solution was prepared with DMSO (100 mg/l). Controls with and without this vehicle were taken for the test. Based on the effect on biomass of the test organism Selenastrum capricornutum, the72hr-NOEC and EC50 values of Dibutyl adipate (CAS No.105 -99 -7) was determined as2.8 and 2.0mg/L, respectively.Thus, based on the EC50 value, it can be concluded that the substance Dibutyl adipate is considered to be toxic to aquatic organisms. Since the test chemical is readily biodegradable in nature, chemical Dibutyl adipate can be considered to be non-toxic to aquatic environment and can be considered to be not classified as per the CLP classification criteria.

 

Thus, based on the overall reported results for target chemicalbutyl 12-acetoxyoctadec-9-enoate(OECD QSAR toolbox version 3.4 and EPI suite, 2017) and for its read across substance (from authoritative database and secondary source), it can be concluded that the test substance butyl 12-acetoxyoctadec-9-enoate can be considered as non-toxic to aquatic environment and thus can be considered to be not classified as per the CLP classification criteria.