3,5-diaminobenzoic acid

Adsorption / desorption

Link to relevant study record(s)

Reference

Endpoint:

adsorption / desorption: screening

Type of information:

experimental study

Adequacy of study:

key study

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Qualifier:

according to guideline

Guideline:

OECD Guideline 121 (Estimation of the Adsorption Coefficient (Koc) on Soil and on Sewage Sludge using High Performance Liquid Chromatography (HPLC))

Principles of method if other than guideline:

To determine Adsorption coefficient (KOC) on soil and on sewage sludge of the 3,5-diaminobenzoic acid(CAS No.535-87-5) using HPLC.

GLP compliance:

no

Type of method:

HPLC estimation method

Media:

soil/sewage sludge

Specific details on test material used for the study:

- EC name: 3,5 Diaminobenzoic acid
- Name of test material (as cited in study report): 3,5-diaminobenzoic acid
- Molecular formula (if other than submission substance): C7H5NO4
- Molecular weight (if other than submission substance): 167.1195 g/mol
- Smiles notation (if other than submission substance): c1(cc(ccc1)[N+](=O)[O-])C(=O)O
- InChI: 1S/C7H5NO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H,(H,9,10)
- Substance type: Organic
- Physical state: Solid

SOURCE OF TEST MATERIAL
- Source and lot/batch No.of test material:L146261701
- Expiration date of the lot/batch:1/12/2021

STABILITY AND STORAGE CONDITIONS OF TEST MATERIAL
- Storage condition of test material:In Refrigerator (2-8 °C)

Radiolabelling:

not specified

Test temperature:

25°C

Details on study design: HPLC method:

The solutions of the test substance and reference substances were prepared in the mobile phase. Each of the reference substance and test substance were analysed by HPLC at 210 nm.
After equilibration of the HPLC system, Urea was injected first, the reference substances were injected in duplicate, followed by the test chemical solution in duplicate. Reference substances were injected again after test sample, no change in retention time of reference substances was observed.
Retention time tR were measured, averaged and the decimal logarithms of the capacity factors k were calculated. The graph was plotted between log Koc versus log k(Annex - 2).The linear regression parameter of the relationship log Koc vs log k were also calculated from the data obtained with calibration samples and therewith, log Koc of the test substance was determined from its measured capacity factor.
Operating Conditions:
HPLC Model No. : Agilent Technologies,1260 Infinity
Flow Rate : 1.0 mL/min
Column : ZORBAX Eclipse Plus C18, 4.6×100mm, 3.5 μm
Mobile phase : Acetonitrile: water (55:45)
Temperature : 25°C
Detector : Diode Array Detector @210nm
Injector : Autosampler
Injector volume : 10μl
Data Acquisition software : ChemStationOpen lab Control Panel

Details on test conditions:

A test item solution was prepared by accurately weighing 5 mg of test item and diluted with mobile phase up to 10 ml. Thus, the test solution concentration was 500 mg/l. The pH of test substance was 5.66

Key result

Type:

log Koc

Value:

2.961 dimensionless

pH:

5.66

Temp.:

25 °C

Remarks on result:

other: Log Koc reported as 2.961 ± 0.003

Transformation products:

not specified

Test substance 3,5-diaminobenzoic acid		K	Log k	Log Koc by Generalized Calibration Graph	Mean of Log Koc ± S.D.
tR1	0.803	-0.17	0.769	2.959	2.961 ± 0.003
tR2	0.804	-0.169	0.772	2.963

Validity criteria fulfilled:

yes

Conclusions:

The Adsorption Coefficient of test substance 3,5-diaminobenzoic acid (CAS No. 535-87-5)was determined as per the HPLC method (OECD Guideline-121). The Log Koc value was found to be 2.961 ± 0.003 at 25°C.

Executive summary:

The adsorption coefficient Koc in soil and in sewage sludge 3,5-diaminobenzoic acid(CAS No.535-87-5) was determined by the Reverse Phase High Performance Liquid Chromatographic method according to OECD Guideline No. 121 for testing of Chemicals. The reference substances were chosen according to functional similarity with the test substance and calibration graph was prepared. The reference substances were 4 -chloroaniline, 2 - nitrophenol, Nitrobenzene, 4-Nitrobenzamide, Benzamide having Koc value ranging from 1.239 to 2.47 The Log Koc value was found to be 2.961 ± 0.003at 25°C.

Description of key information

The adsorption coefficient Koc in soil and in sewage sludge 3,5-diaminobenzoic acid(CAS No.535-87-5) was determined by the Reverse Phase High Performance Liquid Chromatographic method according to OECD Guideline No. 121 for testing of Chemicals. The reference substances were chosen according to functional similarity with the test substance and calibration graph was prepared. The reference substances were 4 -chloroaniline, 2 - nitrophenol, Nitrobenzene, 4-Nitrobenzamide, Benzamide having Koc value ranging from 1.239 to 2.47 The Log Koc value was found to be 2.961 ± 0.003at 25°C.

Key value for chemical safety assessment

Koc at 20 °C:

914.11

Additional information

Four studies which includes one experimental and remaining three supporting predicted values from validated models for adsorption endpoint of the target chemical 3,5 Diaminobenzoic acid (Cas no. 535-87-5) were reviewed to summarize as follows: 

 

First experimental study from UERL laboratory;2017 suggest the adsorption coefficient Koc in soil and in sewage sludge 3,5-diaminobenzoic acid(CAS No.535-87-5) was determined by the Reverse Phase High Performance Liquid Chromatographic method according to OECD Guideline No. 121 for testing of Chemicals. The reference substances were chosen according to functional similarity with the test substance and calibration graph was prepared. The reference substances were 4 -chloroaniline, 2 - nitrophenol, Nitrobenzene, 4-Nitrobenzamide, Benzamide having Koc value ranging from 1.239 to 2.47 The Log Koc value was found to be 2.961 ± 0.003at 25°C.

Above experimental study supported by prediction using EPI suite  KOCWIN (v2.00) program as Koc 10 L/kg(log Koc=1) by means of MCI method at 25 deg.C. This Koc value indicates that the substance 3,5 Diaminobenzoic acid has a Negligible sorption to soil and sediment and therefore have rapid migration potential to groundwater. 

Whereas another predicted database SciFinder, American Chemical Society (ACS); 2017 indicate the soil adsorption coefficient i.e Koc value of test substance 3,5 Diaminobenzoic acid was estimated to be 1 (dimensionless) at 1-2 and 6-10 pH, 1.46 at pH 3,3.91 at pH 4 and 2.97 at pH 5 and temperature 25 deg.C.

And from Chemspider - ACD/PhysChem Suite also support to both results i.e the soil adsorption coefficient i.e Koc value of test substance 3,5 Diaminobenzoic acid was estimated to be 2.56 at pH 5.5 and KOC=1.00 at pH 7.4 and temp.25 deg.C

 

Thus based on the above all available studies for target chemical 3,5 Diaminobenzoic acid (Cas no. 535-87-5) concluded that it is expected to have high to moderate mobility in soil and sediment compartment.

[LogKoc: 2.961]