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Hydrolysis

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Reference
Endpoint:
hydrolysis
Type of information:
calculation (if not (Q)SAR)
Adequacy of study:
key study
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
Reference:
Composition 1
Qualifier:
according to
Guideline:
other: Modeling database
Principles of method if other than guideline:
HYDROWIN Program (v2.00) from EPI Suite estimation database
GLP compliance:
not specified
Test material information:
Composition 1
Specific details on test material used for the study:
Name of the test chemical: (2E)-3,7-dimethylocta-2,6-dien-1-yl 2-phenylacetate
Common Name: Geranyl phenylacetate
Molecular formula: C18H24O2
Molecular weight: 272.3856 g/mol
Smiles Notation: c1(CC(OC\C=C(\CC\C=C(\C)C)C)=O)ccccc1
InChI: 1S/C18H24O2/c1-15(2)8-7-9-16(3)12-13-20-18(19)14-17-10-5-4-6-11-17/h4-6,8,10-12H,7,9,13-14H2,1-3H3/b16-12+
Substance Type: Organic
Physical State: Liquid (colorless)
Radiolabelling:
not specified
Analytical monitoring:
not specified
Estimation method (if used):
HYDROWIN v2.00
Transformation products:
not specified
Temp.:
25 °C
Hydrolysis rate constant:
0.581 s-1
Type:
not specified
Remarks on result:
other: at pH greater than 8
pH:
8
Half-life:
13.803 d
Type:
not specified
Remarks on result:
other: other details not available.
pH:
7
Half-life:
138.033 d
Type:
not specified
Remarks on result:
other: other details not available

HYDROWIN Program (v2.00) Results:

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

SMILES : c1(CC(=O)(OCC=C(CCC=C(C)C)C))ccccc1

CHEM  :

MOL FOR: C18 H24 O2

MOL WT : 272.39

--------------------------- HYDROWIN v2.00 Results ---------------------------

 

 

NOTE: Fragment(s) on this compound are NOT available from the fragment

library. Substitute(s) have been used!!! Substitute R1, R2, R3,

or R4 fragments are marked with double astericks "**".

 

ESTER: R1-C(=O)-O-R2                  R1: -CH2-Phenyl

** R2: -CH2-CH=CH2

Kb hydrolysis at atom # 3: 5.812E-001 L/mol-sec

 

Total Kb for pH > 8 at 25 deg C : 5.812E-001 L/mol-sec

Kb Half-Life at pH 8:     13.803 days

Kb Half-Life at pH 7:    138.033 days

Validity criteria fulfilled:
not specified
Conclusions:
The hydrolysis half life at different pH and rate constant of test chemical (2E)-3,7-dimethylocta-2,6-dien-1-yl 2-phenylacetate (CAS No. 102-22-7) was estimated by EPI  Suite (HydroWin). The Half life estimated at pH 7 was 138.033 days and at pH 8 was 13.803 days at temperature 25 oC. The rate Constant at pH > 8 was 0.5812 L/Mol/Sec  at 25 oC. Since, half life of hydrolysis of chemical (2E)-3,7-dimethylocta-2,6-dien-1-yl 2-phenylacetate is more than 10 days it shows negligible hydrolysis in water.
Executive summary:

The hydrolysis half life at different pH and rate constant of test chemical (2E)-3,7-dimethylocta-2,6-dien-1-yl 2-phenylacetate (CAS No. 102-22-7) was estimated by EPI  Suite (HydroWin). The Half life estimated at pH 7 was 138.033 days and at pH 8 was 13.803 days at temperature 25 oC. The rate Constant at pH > 8 was 0.5812 L/Mol/Sec  at 25 oC. Since, half life of hydrolysis of chemical (2E)-3,7-dimethylocta-2,6-dien-1-yl 2-phenylacetate is more than 10 days it shows negligible hydrolysis in water.

Description of key information

The hydrolysis half life at different pH and rate constant of test chemical (2E)-3,7-dimethylocta-2,6-dien-1-yl 2-phenylacetate (CAS No. 102-22-7) was estimated by EPI  Suite (HydroWin). The Half life estimated at pH 7 was 138.033 days and at pH 8 was 13.803 days at temperature 25 oC. The rate Constant at pH > 8 was 0.5812 L/Mol/Sec  at 25 oC. Since, half life of hydrolysis of chemical (2E)-3,7-dimethylocta-2,6-dien-1-yl 2-phenylacetate is more than 10 days it shows negligible hydrolysis in water.

Key value for chemical safety assessment

Half-life for hydrolysis:
138.033 d
at the temperature of:
25 °C

Additional information

Predicted data for target compound (2E)-3,7-dimethylocta-2,6-dien-1-yl 2-phenylacetate (CAS No. 102-22-7) and supporting weight of evidence studies for its read across chemicals were reviewed for the Hydrolysis endpoint which is summarized below.

In a prediction done to estimate the hydrolysis half life at different pH and rate constant of test chemical (2E)-3,7-dimethylocta-2,6-dien-1-yl 2-phenylacetate (CAS No. 102-22-7) by EPI Suite (Estimation Program Interface, 2017) HydroWin Program v.2.00. Estimated Half life at pH 7 was 138.033 days and at pH 8 was 13.803 days at temperature 25 oC. The rate Constant at pH > 8 was 0.5812 L/Mol/Sec at 25 oC. Since, half life of hydrolysis of chemical (2E)-3,7-dimethylocta-2,6-dien-1-yl 2-phenylacetate is more than 10 days it shows negligible hydrolysis in water.

In a supporting weight of evidence study from authoritative database Hazardous Substance Data Bank ( HSDB, 2017) of read across chemical eth(5-benzylfuran-3-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate (CAS no. 10453 -86 -8) hydrolysis rate constant obtained was 0.17 L/mol/sec by structure estimation method and second order reaction. The half life of hydrolysis obtained at pH 7 was 1.3 years and at pH 8 was 47 days. Since half life of hydrolysis at both pH is more than 10 days so it is concluded that read across chemical eth(5-benzylfuran-3-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate shows negligible hydrolysis.

In another supporting weight of evidence study from same source as mentioned above ( HSDB, 2017) of read across chemical of read across chemical (2E)-3,7-dimethylocta-2,6-dien-1-yl acetate the hydrolysis rate constant obtained was 0.35 L/mol/sec by base catalysed second order reaction and structure estimation method. The half life of hydrolysis obtained at pH 7 was 231 days and at pH 8 was 23 days. Since half life of hydrolysis at both pHs is more than 10 days so it is concluded that test chemical (2E)-3,7-dimethylocta-2,6-dien-1-yl acetate shows negligible hydrolysis.

On the basis of results for target chemical (2E)-3,7-dimethylocta-2,6-dien-1-yl 2-phenylacetate (CAS No. 102-22-7) (From EPI Suite ) and for its read across chemicals (from HSDB, 2017) it is concluded that target chemical (2E)-3,7-dimethylocta-2,6-dien-1-yl 2-phenylacetate is expected to show negligible hydrolysis.