Diethyl 4-oxopentane-1,2-dicarboxylate

Long-term toxicity to aquatic invertebrates

Administrative data

Endpoint:

long-term toxicity to aquatic invertebrates

Type of information:

(Q)SAR

Adequacy of study:

key study

Study period:

September 28, 2012

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Estimation method using accepted and valid (Q)SAR method.

Justification for type of information:

QSAR prediction: migrated from IUCLID 5.6

Data source

Reference

Reference 1

Reference Type:

other: software

Title:

Unnamed

Year:

2011

Reference 2

Reference Type:

study report

Title:

Unnamed

Year:

2012

Report date:

2012

Materials and methods

Test guideline

Guideline:

other: ECHA Guidance on information requirements and chemical safety assessment - Chapter R.06: QSARs and grouping of chemicals - May 2008

Principles of method if other than guideline:

SARs have been used by the U.S. Environmental Protection Agency since 1981 to predict the aquatic toxicity of new industrial chemicals in the absence of test data. The acute toxicity of a chemical to fish (both fresh and saltwater), water fleas (daphnids), and green algae has been the focus of the development of SARs, although for some chemical classes SARs are available for other effects (e.g, chronic toxicity and bioconcentration factor) and terrestrial organisms (e.g., earthworms). SARs are developed for chemical classes based on measured test data that have been submitted by industry or they are developed by other sources for chemicals with similar structures, e.g., phenols. Using the measured aquatic toxicity values and estimated Kow values, regression equations can be developed for a class of chemicals. Toxicity values for new chemicals may then be calculated by inserting the estimated Kow into the regression equation and correcting the resultant value for the molecular weight of the compound.

The structure-activity relationships (SARs) presented in ECOSAR are used to predict the aquatic toxicity of chemicals based on their similarity of structure to chemicals for which the aquatic toxicity has been previously measured. Most SAR calculations in the ECOSAR Class Program are based upon the octanol/water partition coefficient (Kow). Various surfactant SAR calculations are based upon the average length of carbon chains or the number of ethoxylate units.

Test material

Test material information

Constituent 1

Reference substance name:

Diethyl 4-oxopentane-1,2-dicarboxylate

EC Number:

413-860-0

EC Name:

Diethyl 4-oxopentane-1,2-dicarboxylate

Cas Number:

1187-74-2

Molecular formula:

C11H18O5

IUPAC Name:

1,4-diethyl 2-(2-oxopropyl)butanedioate

Details on test material:

SMILES: O=C(OCC)CC(C(=O)OCC)CC(=O)C
Experimental log Kow: 1.3
Experimental Water Solubility: 27960 mg/L

Test organisms

Test organisms (species):

other: Daphnid

Study design

Water media type:

freshwater

Results and discussion

Effect concentrations

Duration:

21 d

Dose descriptor:

other: ChV (Chronic Value )

Effect conc.:

133.7 mg/L

Nominal / measured:

estimated

Conc. based on:

test mat.

Basis for effect:

not specified

Any other information on results incl. tables

------------------------ ECOSAR v1.00 Results ------------------------

Compound Being Estimated:

SMILES: O=C(OCC)CC(C(=O)OCC)CC(=O)C

CHEM: diethyl 4-oxopentane-1,2-dicarboxylate

MOL FOR: C11 H18 O5

MOL WT : 230.26

Log Kow: 1.30 (User entered)

Melt Pt: -65.00 deg C

Wat Sol: 27960 mg/L (measured)

ECOSAR v1.00 Class(es) Found

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

Esters

 

ECOSAR Class	Organism	Duration	End Pt	Predicted mg/L (ppm)
Esters	Fish	96-hr	LC50	78.671
Esters	Fish	14-day	LC50	32376.088 *
Esters	Daphnid	48-hr	LC50	176.976
Esters	Green Algae	96-hr	EC50	81.321
Esters	Fish	32/33-d	ChV	8.363
Esters	Daphnid	21-day	ChV	133.713
Esters	Green Algae		ChV	16.323
Esters	Fish (SW)	96-hr	LC50	126.594
Esters	Mysid Shrimp	96-hr	LC50	164.034
Esters	Fish (SW)		ChV	16.176 !
Esters	Mysid Shrimp (SW)		ChV	53322.965 *
Esters	Earthworm	14-day	LC50	5047.826

 

 

Neutral Organic SAR (Baseline Toxicity)	Fish	96-hr	LC50	693.848
	Daphnid	48-hr	LC50	367.887
	Green Algae	96-hr	EC50	119.008
	Fish		ChV	66.894
	Daphnid		ChV	30.023
	Green Algae		ChV	37.902

Note: * = asterisk designates: Chemical may not be soluble  enough to measure this predicted effect.

Note: ! = exclamation designates: The toxicity value was determined froma predicted SAR using established acute-to-chronic ratios and ECOSAR regression techniques which are documented in the supporting Technical Reference Manual. When possible, this toxicity value should be considered in a weight of evidence approach.

 

Esters:

------

 For Fish LC50 (96-h), Daphnid LC50, Mysid: If the log Kow is greaterthan 5.0, or if the compound is solid and the LC50 exceeds the watersolubility by 10X, no effects at saturation are predicted.

  For Fish LC50 (14-day) and Earthworm LC50: If the log Kow is greaterthan 6.0, or if the compound is solid and the LC50 exceeds the watersolubility by 10X, no effects at saturation are predicted.

  For Green Algae Acute Toxicity Values: If the log Kow of the chemical isgreater than 6.4, or if the compound is solid and the EC50 exceeds the watersolubility by 10X, no effects at saturation are predicted for these endpoints.

  For All Chronic Toxicity Values: If the log Kow of the chemical is greaterthan 8.0, or if the compound is solid and the ChV exceeds the water solubilityby 10X, no effects at saturation are predicted for these endpoints.

 

ECOSAR v1.00 SAR Limitations:

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

Maximum LogKow: 5.0 (Fish 96-hr LC50; Daphnid LC50, Mysid LC50)

Maximum LogKow: 6.0 (Fish 14-day LC50; Earthworm LC50)

Maximum LogKow: 6.4 (Green Algae EC50)

Maximum LogKow: 8.0 (ChV)

Maximum Mol Wt: 1000

 

Baseline Toxicity SAR Limitations:

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

Maximum LogKow: 5.0 (Fish 96-hr LC50; Daphnid LC50)

Maximum LogKow: 6.4 (Green Algae EC50)

Maximum LogKow: 8.0 (ChV)

Maximum Mol Wt: 1000

Applicant's summary and conclusion

Validity criteria fulfilled:

yes

Conclusions:

The ECOSAR model is a reliable and appropriate QSAR model to apply to diethyl 4-oxopentane-1,2-dicarboxylate, as it is based on a chemical database that calculates the toxicity of esters, which exhibit excess toxicity in addition to narcosis.
The predicted long-term (21-d) toxicity ChV for daphnid is 133.7 mg/L.

Executive summary:

The predicted long-term (21-d) toxicity ChV for daphnid is 133.7 mg/L.