Pentyl phenylacetate

Toxicity to microorganisms

Link to relevant study record(s)

Reference

Endpoint:

toxicity to microorganisms

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:

Data is predicted using OECD QSAR toolbox version 3.4 and QMRF report has been attached

Qualifier:

according to guideline

Guideline:

other: estimated data

Principles of method if other than guideline:

Prediction was done by using OECD QSAR toolbox v3.4

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of the test material: pentyl 2-phenylacetate
- IUPAC name: pentyl 2-phenylacetate
- Molecular formula: C13H18O2
- Molecular weight: 206.283 g/mol
- Substance type: Organic
- Smiles: C(=O)(Cc1ccccc1)OCCCCC
- Physical State: Liquid

Analytical monitoring:

not specified

Details on sampling:

No data available

Vehicle:

not specified

Details on test solutions:

No data available

Test organisms (species):

Tetrahymena pyriformis

Test type:

static

Water media type:

freshwater

Total exposure duration:

48 h

Key result

Duration:

48 h

Dose descriptor:

other: IGC50

Effect conc.:

19.586 mg/L

Nominal / measured:

nominal

Conc. based on:

test mat.

Basis for effect:

other: growth

Remarks on result:

other: No other details available

The prediction was based on dataset comprised from the following descriptors: IGC50
Estimation method: Takes average value from the 5 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 ( not "l") )  )  and ("m" and "n" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Esters (Acute toxicity) by US-EPA New Chemical Categories

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Michael addition AND Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals AND Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Arenes by DNA binding by OECD

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Esters by Acute aquatic toxicity MOA by OASIS

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Esters by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as No alert found by DNA binding by OASIS v.1.4

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as AN2 OR AN2 >>  Michael-type addition, quinoid structures OR AN2 >>  Michael-type addition, quinoid structures >> Quinones and Trihydroxybenzenes OR AN2 >> Michael-type conjugate addition to activated alkene derivatives OR AN2 >> Michael-type conjugate addition to activated alkene derivatives >> Alpha-Beta Conjugated Alkene Derivatives with Geminal Electron-Withdrawing Groups OR AN2 >> Schiff base formation by aldehyde formed after metabolic activation OR AN2 >> Schiff base formation by aldehyde formed after metabolic activation >> Geminal Polyhaloalkane Derivatives OR AN2 >> Shiff base formation after aldehyde release OR AN2 >> Shiff base formation after aldehyde release >> Specific Acetate Esters OR AN2 >> Shiff base formation for aldehydes OR AN2 >> Shiff base formation for aldehydes >> Haloalkane Derivatives with Labile Halogen OR Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Coumarins OR Non-covalent interaction >> DNA intercalation >> Quinones and Trihydroxybenzenes OR Radical OR Radical >> Radical mechanism via ROS formation (indirect) OR Radical >> Radical mechanism via ROS formation (indirect) >> Coumarins OR Radical >> Radical mechanism via ROS formation (indirect) >> Geminal Polyhaloalkane Derivatives OR Radical >> Radical mechanism via ROS formation (indirect) >> p-Substituted Mononitrobenzenes OR Radical >> Radical mechanism via ROS formation (indirect) >> Quinones and Trihydroxybenzenes OR Radical >> Radical mechanism via ROS formation (indirect) >> Single-Ring Substituted Primary Aromatic Amines OR SN1 OR SN1 >> Nucleophilic attack after carbenium ion formation OR SN1 >> Nucleophilic attack after carbenium ion formation >> Specific Acetate Esters OR SN1 >> Nucleophilic attack after nitrenium ion formation OR SN1 >> Nucleophilic attack after nitrenium ion formation >> Single-Ring Substituted Primary Aromatic Amines OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> p-Substituted Mononitrobenzenes OR SN2 OR SN2 >> Acylation OR SN2 >> Acylation >> Specific Acetate Esters OR SN2 >> Acylation involving a leaving group  OR SN2 >> Acylation involving a leaving group  >> Haloalkane Derivatives with Labile Halogen OR SN2 >> Acylation involving a leaving group after metabolic activation OR SN2 >> Acylation involving a leaving group after metabolic activation >> Geminal Polyhaloalkane Derivatives OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom >> Haloalkane Derivatives with Labile Halogen OR SN2 >> Direct acting epoxides formed after metabolic activation OR SN2 >> Direct acting epoxides formed after metabolic activation >> Coumarins OR SN2 >> Nucleophilic substitution at sp3 Carbon atom OR SN2 >> Nucleophilic substitution at sp3 Carbon atom >> Specific Acetate Esters OR SN2 >> Nucleophilic substitution at sp3 carbon atom after thiol (glutathione) conjugation OR SN2 >> Nucleophilic substitution at sp3 carbon atom after thiol (glutathione) conjugation >> Geminal Polyhaloalkane Derivatives by DNA binding by OASIS v.1.4

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as Michael addition AND Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals AND Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Arenes by DNA binding by OECD

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Acylation OR Acylation >> P450 Mediated Activation to Isocyanates or Isothiocyanates OR Acylation >> P450 Mediated Activation to Isocyanates or Isothiocyanates >> Benzylamines-Acylation OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Hydroquinones OR Michael addition >> Polarised Alkenes-Michael addition OR Michael addition >> Polarised Alkenes-Michael addition >> Alpha, beta- unsaturated esters OR No alert found OR Schiff base formers OR Schiff base formers >> Chemicals Activated by P450 to Mono-aldehydes OR Schiff base formers >> Chemicals Activated by P450 to Mono-aldehydes >> Benzylamines-Schiff base OR Schiff base formers >> Direct Acting Schiff Base Formers OR Schiff base formers >> Direct Acting Schiff Base Formers >> Mono aldehydes OR SN1 OR SN1 >> Iminium Ion Formation OR SN1 >> Iminium Ion Formation >> Aliphatic tertiary amines OR SN1 >> Nitrenium Ion formation OR SN1 >> Nitrenium Ion formation >> Primary aromatic amine OR SN1 >> Nitrenium Ion formation >> Secondary aromatic amine OR SN2 OR SN2 >> SN2 at an sp3 Carbon atom OR SN2 >> SN2 at an sp3 Carbon atom >> Aliphatic halides by DNA binding by OECD

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Non binder, without OH or NH2 group by Estrogen Receptor Binding

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Moderate binder, OH grooup OR Strong binder, OH group by Estrogen Receptor Binding

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as Alkyl substituent on aromatic ring AND Aromatic-CH2 AND Aromatic-H AND Benzene AND -CH2-  [linear] AND Ester   [-C(=O)-O-C] AND Linear C4 terminal chain  [CCC-CH3] AND Methyl  [-CH3] AND Unsubstituted phenyl group (C6H5-) by Bioaccumulation - metabolism alerts

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Aliphatic alcohol  [-OH] OR Aliphatic amine   [-NH2  or  -NH-] OR Aromatic-CH OR Aromatic-CH3 OR Carbon with 4 single bonds & no hydrogens OR -CH-   [linear] OR Cyanide / Nitriles   [-C#N] OR Pyridine ring OR Sulfonic acid / salt -> aromatic attach by Bioaccumulation - metabolism alerts

Domain logical expression index: "m"

Parametric boundary:The target chemical should have a value of log Kow which is >= 2.08

Domain logical expression index: "n"

Parametric boundary:The target chemical should have a value of log Kow which is <= 4.5

Validity criteria fulfilled:

not specified

Conclusions:

IGC 50 value of test chemical pentyl 2-phenylacetate was estimated to be 19.58 mg/L when test chemical was exposed to Tetrahymena pyriformis for 48 hrs.

Executive summary:

Toxicity to microorganisms of target chemical pentyl 2-phenylacetate was estimated by using OECD QSAR tool box v3.4 using Log kow as primary descriptor

and considering five closest read across substances. IGC50 value of target chemical pentyl 2-phenylacetate was estimated to be 19.58 mg/L when

exposed to Tetrahymena pyriformis for 48 hrs.

Description of key information

Toxicity to microorganisms:

Toxicity to microorganisms of target chemical pentyl 2-phenylacetate was estimated by using OECD QSAR tool box v3.4 using Log kow as primary descriptor

and considering five closest read across substances. IGC50 value of target chemical pentyl 2-phenylacetate was estimated to be 19.58 mg/L when

exposed to Tetrahymena pyriformis for 48 hrs.

Key value for chemical safety assessment

EC50 for microorganisms:

19.58 mg/L

Additional information

Toxicity to microorganisms:

Toxicity to microorganisms of target chemical pentyl 2-phenylacetate was estimated by using OECD QSAR tool box v3.4 using Log kow as primary descriptor and considering five closest read across substances. IGC50 value of target chemical pentyl 2-phenylacetate was estimated to be 19.58 mg/L when exposed to Tetrahymena pyriformis for 48 hrs.

The above prediction was supported by experimental result summarized in Toxicology methods; Vol. 7, No. 4; Pages 289-309; 1997 for structurally similar read across substance Methyl phenylacetate (101-41-7)

A short-term, static protocol using the common freshwater ciliate Tetrahymena pyriformis (strain GL-C) was reported. The 50% impairment growth concentration (IGC 50) is the endpoint of choice. Cultures were reared in 50 mL of a semi defined medium in 250-mL Erlenmeyer flasks. Definitive test replicates consisted of a minimum of 5 different concentrations of each test material. Duplicate flasks were inoculated to an initial density of 2500 cells/ mL with log-growth phase ciliates. Following 40 h of incubation at 27 deg C, population density was measured spectrophotometrically and 50% effect levels were determined.

The impairment growth concentration (IGC50) of Methyl phenylacetate in microorganism [Tetrahymena pyriformis] in a 48 hr study on the basis of growth inhibition effect using a short-term, static protocol was observed to be 377 mg/L.

The above experimental data was further supported by experimental result summarized in J. Soc. Cosmet. Chem. Jpn, 27 (3) 227-241 (1993) for the structurally similar read across substance Benzyl isobutyrate (103-28-6)

Muller Hinton agar medium in culture dishes (35*10mm) was used for the measurement of MIC. Various concentrations of fragrance materials were prepared in ethyl alcohol or DMSO depending on the solubility of the materials. The bacteria tested were pre-propagated with sensitivity test broth of NISSUI using shaking culture. The incubated mediums were diluted by 0.75% physiological saline to the microbial concentration of 106CFU/ml. In the Muller Hinton agar medium containing fragrance material, 0.1ml of diluted culture solution was inoculated. MIC was determined as the concentration where no growth was observed after 24hrs at 37°C.

 

The Minimum Inhibitory Concentration of Arthrobacter sp.,Corynebacterium minutissimum (CM) ,Staphylococ cus aureus (IAM-1011, (SA)) ,Staphylococcus epidermidis var. (SE),Escherichia coli (ATCC 11775, (EC)) was found to be 2000 mg/l (inoculum 105CFU/plate) after 24 hours exposure to benzyl isobutyrate.