1,2,3,4-tetrahydronaphthalene

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

biodegradation in water: screening tests

Type of information:

experimental study

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Study well documented, meets generally accepted scientific principles, acceptable for assessment

Principles of method if other than guideline:

Method: Standard method for the examination of water and wastewater, Am. Publ. Health Assoc. (1971)

GLP compliance:

no

Oxygen conditions:

aerobic

Inoculum or test system:

other: sea water

Details on inoculum:

- Sampling site: Lavaca Bay, Texas
- seed was developed in seawater
- Feeding: addition of small amounts of settled raw wastewater about  every 3 to 4 days
- Evaporative losses were replaced with distilled water

Duration of test (contact time):

20 d

Initial conc.:

9.215 mg/L

Based on:

test mat.

Parameter followed for biodegradation estimation:

O2 consumption

Details on study design:

- Culturing apparatus: 300 ml BOD bottle
- Number of culture flasks per concentration: 1 or 2 replicates each for  4 sampling times
- Aeration device: Sparging of dilution water with pure oxygen before  test, no further aeration
- Measuring equipment: oxygen meter permitting correction for high  salinity water
- Closed vessels used: yes

- Composition of medium: Synthetic seawater obtained by dissolution in  the following order in 20 l of distilled water of: 557.37 g NaCl, 27.20 g  CaSO4, 63.36 g MgCl2.7H2O, 168.30 g MgCl2, 15.84 g KCl, 3.14 g MgBr2.6H2O 
- Additional substrate: Nutrient salts and buffers as recommended in test  method

CONTROLS: inoculum blank

Reference substance:

other: glucose

Value:

3

Sampling time:

20 d

Details on results:

Kinetic of test substance (in %):
= 3 after 5 and 10 days
Degradation products: not measured

Validity criteria fulfilled:

not specified

Interpretation of results:

other: not ready biodegradable

Reference 2

Endpoint:

biodegradation in water: screening tests

Type of information:

experimental study

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Study well documented, meets generally accepted scientific principles

GLP compliance:

not specified

Oxygen conditions:

aerobic

Inoculum or test system:

other: other bacteria: gram-negative rods

Details on inoculum:

- Species/strain: Six strains of bacteria
- Source: Oil-polluted estuarine waters
- Sampling site: Arthur Kill (New Jersey)
- Method of cultivation: Isolation by addition of 0.05 to 0.1 % sterile  naphthalene (3 strains), 1-methyl naphthalene (1 strain) and 2-methyl  
naphthalene (2 strains) as sole sources of carbon and energy in  Bushnell-Haas broth (Difco) supplemented with 3% NaCl

Duration of test (contact time):

>= 18 - <= 24 h

Details on study design:

- Culturing apparatus: Fernbach flasks with 1 l of test solution
- Number of culture flasks per concentration: 1
- Aeration device: shaking (200 rpm)
- Composition of medium: potassium phosphate buffer (0.05M)
- Test temperature: 27 degree C
- pH value: 6.8

SAMPLING: End of study: (1) Centrifugation (2), acidification of  supernatant, (3) extraction with diethyl ether, (4) GC / FID / MS TEST CONDITIONS

Details on results:

One out of six strains o marine bacteria grown on naphthalene was able to metabolize tetrahydronaphthalene, converting it into a ketone tetrahydronaphthalone. The position of the keto group could not be determined.

Degradation products: yes

Interpretation of results:

other: The typical route of biodegradation of naphthalene is not followed with tetrahydronaphthalene

Conclusions:

The typical route of biodegradation of naphthalene is not followed with tetrahydronaphthalene, where initial attack by
naphthalene-grown bacteria occurs on the saturated ring.

Executive summary:

The metabolism of polynuclear aromathic hydrocarbons was studied. The results indicate that one of the six strains grown on naphthalene was able to metabolize tetrahydronaphthalene, converting it into a ketone tetrahydronaphthalone. The position of the keto group could not be determined.

Reference 3

Endpoint:

biodegradation in water: screening tests

Type of information:

experimental study

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Study well documented, meets generally accepted scientific principles, acceptable for assessment; Restrictions: - identification by Kovats's index may be erroneous; - disappearance of peak indicates primary, not ultimate degradation

Principles of method if other than guideline:

Method: other: see Test Conditions

GLP compliance:

no

Oxygen conditions:

aerobic

Inoculum or test system:

other: sea water

Details on inoculum:

- Type: sea water
- Source: North Sea coast
- Sampling site: not reported

Duration of test (contact time):

10 d

Initial conc.:

12.4 µg/L

Based on:

test mat.

Details on study design:

TEST CONDITIONS
- Composition of medium: not reported
- Additional substrate: nitrogen and phosphorus salts for biodegradation  phase
- Test temperature: 25 degree C
- Aeration device: none
- CONTROLS: evaporation control, negative control inhibited with copper sulphate
- ADDITIONAL EXPERIMENTS: Similar tests at 20 degree C with durations of 2,  4, 7, and 14 days were performed but evaluated only quantitatively,  
leading to a classification of the biodegradation rate.

Value:

> 99.2

Sampling time:

10 d

Details on results:

- Evaporation control (room temperature) 66 % loss in 2 hours, 99 % loss in 24 hours
- Concentration of 1,2,3,4-tetrahydronaphthalene (total oil):
Start solution: 12.4 (1162) µg/l
Inhibited control: 14.3 (1285) µg/l
Test solution (end of test): < 0.1 (11.2 µg/l)
- Classification of biodegradation rate: "moderate"

Conclusions:

The authors concluded that the biodegradation rate is "moderate"

Reference 4

Endpoint:

biodegradation in water: screening tests

Type of information:

experimental study

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Well docuemened publication

Principles of method if other than guideline:

hydrocarbon co-oxidation test

GLP compliance:

no

Oxygen conditions:

aerobic

Inoculum or test system:

other: Nocardia sp.

Details on inoculum:

INOCULUM/TEST ORGANISM
- Species/strain: Nocardia corallina strain V-49
- Source: isolated from soil

Details on study design:

TEST SYSTEM
- Culturing apparatus: agar-resin plate or 40-liter stirred fermentor

TEST CONDITIONS
- Additional substrate: n-hexadecane or Cerelose

Details on results:

Nocardia coralina strain V-49 degrades tetrahydronaphthalene to 4-(2-hydroxyphenyl)butanoic acid

Degradation products: yes

Interpretation of results:

other: degradation observed but not quantified

Conclusions:

Nocardia coralina degraded tetrahydronapthalene when available as co-substrate ina medium with other hydrocarbons

Executive summary:

Nocardia coralina degraded tetrahydronapthalene when available as co-substrate ina medium with other hydrocarbons by mean of ring cleavage to 4 phenyl-2 -OH butiric acid

Reference 5

Endpoint:

biodegradation in water: screening tests

Type of information:

experimental study

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Well documented publication

GLP compliance:

no

Oxygen conditions:

aerobic

Details on inoculum:

- Species/strain: Pseudomonas stutzeri AS39; 41 other strains
- Sampling site: 41 strains isolated from 32 different samples of polluted soils, mud, and waters from West Germany;   Pseudomonas stutzeri AS39 isolated from a coal dump overlayed by partly  recultivated soil near Herten, Germany

Duration of test (contact time):

2 d

Details on study design:

- Method of cultivation:    Liquid cultures: Mineral salts medium (Dorn et al. 1974);   Solid media: 1.5 % Bacto agar added to liquid medium;   Supplementation: 0.05 % Yeast extract or vitamins solution


TEST SYSTEM
- Culturing apparatus:    <= 100 ml: shaking flasks   <= 200 ml: cylindrical bubbling columns   <= 750 ml: 1 l-fermentors
- Aeration device: Depending on apparatus, supported by magnetic stirring
- Closed vessels used: yes (teflon lined screwcaps)

ANALYTICAL PARAMETER: 
- Test substance consumed: Sorption to cartridges, UV absorption
- Metabolites formed: Sorption to cartridges, elution, GC; identification  by retention times / authentic standards
- Growth: Cell counting

TEST CONDITIONS
- Test temperature: 30 degree C
- Other relevant factors: Addition of test substance via vapor phase,  i.e. with the aeration flow or from reservoirs in the test vessels

CONTROLS: blank plates

Details on results:

- Growth with 1,2,3,4-tetrahydonaphthalene as the sole carbon source  occurred in several mixed cultures but in none of the 41 strains in pure  culture.
- Pseudomonas stutzeri AS39 grew with 1,2,3,4-tetrahydronaphthalene  vapour only in liquid culture. Salicylate-grown cells but not  acetate-grown cells oxidized 1,2,3,4-tetrahydronaphthalene.
- Products of 1,2,3,4-tetrahydronaphthalene conversion by Pseudomonas  stutzeri AS39 and by the other strains were:   1,2,3,4-tetrahydro-1-naphthol (CAS No. 529-33-9) and   1,2,3,4-tetrahydro-1-oxonaphthalene (CAS No. 529-34-0)
- Transformation and growth rates were low, which according to the  authors is probably due to slow transport of 1,2,3,4-tetrahydonaphthalene  to the reaction centers.

Interpretation of results:

other: P. stutzeri AS39 can grow in Tetralin as unic carbon source

Conclusions:

P. stutzeri AS39 can grow in Tetralin as unic carbon source

Executive summary:

A bacterium capable of growing on Tetrahydronaphthalene as the sole source of carbon and energy has been isolated fromsoil of a coal dump. The bacterium was identified as Pseudomonas stutzeri

Reference 6

Endpoint:

biodegradation in water: screening tests

Type of information:

experimental study

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Study well documented, meets generally accepted scientific principles, acceptable for assessment

Principles of method if other than guideline:

Method: batch biodegradation assay with autochthonous groundwater microflora

GLP compliance:

no

Oxygen conditions:

aerobic

Inoculum or test system:

other: natural groundwater microflora

Details on inoculum:

- Source: local groundwater, not further identified (natural microbial flora)
- Initial cell concentration: ca. 130 cells/ml

Duration of test (contact time):

12 d

Initial conc.:

2 mg/L

Based on:

test mat.

Parameter followed for biodegradation estimation:

other: test substrate concentration (GC/peak area)

Details on study design:

- Culturing apparatus: 2.8 l sealed flasks with 2 l test solution
TEST CONDITIONS
- Test temperature: 10 degree C
- pH value: initial 7.9, final 7.3
- SAMPLING: Extraction with CH2Cl2
- CONTROLS: addition of HgCl2 to identical solution

Parameter:

% degradation (test mat. analysis)

Value:

100

Sampling time:

10 d

Details on results:

Percent degradation
Days Total 1,2,3,4-Tetrahydronaphthalene
----------------------------------------------------
1 := 0 := 0
2 -1 -1
3 0 -17
4 3 -6
5 3 -13
6 8 -14
7 46 1
8 66 26
9 80 53
10 90 100
11 98 100
12 100 100
After a lag phase of 5-7 days, degradation is rapid and complete.
Additional observation: At concentrations >= 2.0-2.1 mg/l, degradation ceased after 10 days but continued after the addition of NH4Cl, indicating that assimilable nitrogen is a growth-limiting substrate.

Interpretation of results:

other: complete biodegradation in non-standard test

Conclusions:

The fraction of gas oil corresponding to Tetrahydronaphthalene was completely degraded after 10 days of exposure to groundwater microflora

Executive summary:

The degradation of the different components of gas-oil by groundwater microflora was evaluated.

Tetrahydronaphtalene was completely degraded after 10 days.

Reference 7

Endpoint:

biodegradation in water: screening tests

Type of information:

experimental study

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Study well documented, meets generally accepted scientific principles, acceptable for assessment

Principles of method if other than guideline:

anaerobic degradation with sulphate reducing enrichment culture

GLP compliance:

no

Oxygen conditions:

anaerobic

Inoculum or test system:

other: sulphate reducing bacteria from contaminated aquifer

Details on study design:

Preparation of inoculum: Subcultures were inoculated with a 10% volume  of the liquid phase in 100-ml serum bottles half-filled with  carbonate-buffered, sulfide-reduced freshwater mineral medium (pH 7.4)  with trace element solution SL10 and 10 mM sulfate.

TEST SYSTEM
- Culturing apparatus: 100-ml serum bottles
- Aeration device: Flushing with N2 / CO2 (80:20)
- Closed vessels used: yes, sealed with rubber stoppers

INITIAL TEST SUBSTANCE CONCENTRATION: 2-4 mg/50 ml A

NALYTICAL PARAMETER: Enrichment and derivatisation of degradation  products, GC-MS analysis, comparison of mass spectra with those of  reference compounds

TEST CONDITIONS
- Test temperature: 30 °C
- pH value: 7.4
SULFIDE MEASUREMENT: continuous

Remarks on result:

other: degradation observed but deg. rate not calculated

Details on results:

- Growth: The culture N47 was able to grow with  1,2,3,4-tetrahydronaphthalene as the sole source of carbon and electrons.
- Metabolic pathway: The proposed initial pathway for the degradation of  1,2,3,4-tetrahydronaphthalene is:   (1) 5,6,7,8-tetrahydro-2-naphthoic acid, i.e. addition of a carbon to  the aromatic ring;   (2) octahydro-2-naphthoic acid isomers, i.e. hydrogenation;   (3) decahydro-2-naphthoic acid isomers, i.e. further hydrogenation; may  be a side reaction;   (4) a C11H16O4-diacid with an aliphatic double bond, i.e. ring  cleavage; may be formed from (2) not via (3);   (5) cis-2-carboxycyclohexylacetic acid, i.e. further degradation. - Common pathway: 5,6,7,8-tetrahydro-2-naphthoic acid and the further  metabolites were also found as a metabolites of naphthalene and of  2-methyl naphthalene in studies with the same culture.
- Labelling experiments:  (a) Using 13C-bicarbonate buffer, the additional carbon was shown (for  naphthalene) to come from the solution. The label was not found in  metabolite (5), indicating that this carbon atom was eliminated again.  (b) Using 13C-naphthalene as starting material (label in position 1), the  molecular weight of all metabolites was increased by one amu. (c) Using perdeuterated naphthalene as starting material, five deuterium  atoms were found in each of the metabolites (4) and (5).

Interpretation of results:

other: Tetrahydronaphthalene was degraded under anaerobic conditions

Conclusions:

Inb the present study it was demonstrated that Tetrahydronapthalene undergoes anaerobic biodegradation by a sulfate-reducing culture

Executive summary:

Anaerobic degradation of Tetrahydronaphthalene was investigated with a sulfate reducing enrichment culture obtained from a contaminated aquifer. Tetrahydronaphthalene was degraded via adition of a C1 unit.

Reference 8

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

experimental study

Adequacy of study:

other information

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Guideline study with restrictions

Qualifier:

equivalent or similar to guideline

Guideline:

OECD Guideline 301 D (Ready Biodegradability: Closed Bottle Test)

Deviations:

not specified

Qualifier:

equivalent or similar to guideline

Guideline:

EU Method C.4-E (Determination of the "Ready" Biodegradability - Closed Bottle Test)

Deviations:

not specified

GLP compliance:

no

Oxygen conditions:

aerobic

Inoculum or test system:

sewage, predominantly domestic (adaptation not specified)

Details on inoculum:

- Sampling site: predominantly domestic WWTP Marl-Ost, sampled 23  November 1988
- Preparation of inoculum: filtration (aerobic), the first 200 ml of the  filtrate were discarded
- Volume used: 0.5 ml/l

Duration of test (contact time):

28 d

Initial conc.:

2 mg/L

Based on:

test mat.

Parameter followed for biodegradation estimation:

O2 consumption

Details on study design:

- Culturing apparatus: 300 ml precision glass bottles
- Number of culture flasks per concentration: 2 per sampling time (0, 5,  15, and 28 days)
- Closed vessels used: yes
- Test temperature: 20 degree C
- Three test batches
a) Inoculated culture medium
b) Inoculated culture medium + 2 mg test substance/L
c) Inoculated culture medium + 2 mg Natriumbenzoat/L

Reference substance:

benzoic acid, sodium salt

Parameter:

% degradation (O2 consumption)

Value:

5

Sampling time:

28 d

Details on results:

Kinetic of test substance (in %):
= 3 after 5 day(s)
= 3 after 15 day(s)
Kinetic of control substance (in %):
= 86 after 28 day(s)

Results with reference substance:

- Test concentration: 2 mg/L
- ThSB: 1.67 mg O2/mg
- Degradation: 86%

Validity criteria fulfilled:

yes

Interpretation of results:

under test conditions no biodegradation observed

Executive summary:

The biodegradability of the test item was studied in a "Closed Bottle Test" similar to OECD 301 D and the EU method C4 E. The results indicate that the test item is not readily biodegradable under the present test conditions. The inocolum concentration was 0.5 ml/L and the initial test substance concentration was 2 mg/L. 5% of the test item degraded within a period of 28 days.

The study was classified as "reliable with restrictions".

Reference 9

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

experimental study

Adequacy of study:

key study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Comparable to guideline study with acceptable restrictions. However, report gives no description of the method, only key data are summarised.

Principles of method if other than guideline:

Method: BODIS (Blok) Test (BOD-test for insoluble substances), Draft ISO Guideline 10708

GLP compliance:

no

Oxygen conditions:

aerobic

Inoculum or test system:

activated sludge (adaptation not specified)

Details on inoculum:

- Sampling site: predominantly domestic WWTP Marl-Ost
- activated sludge

Duration of test (contact time):

28 d

Initial conc.:

45.8 mg/L

Based on:

test mat.

Parameter followed for biodegradation estimation:

O2 consumption

Details on study design:

- Culturing apparatus: 300 ml precision glass bottles
- Number of culture flasks per concentration: 3
- Closed vessels used: yes
- ANALYTICAL PARAMETER: dissolved oxygen

Reference substance:

diethylene glycol

Parameter:

% degradation (O2 consumption)

Value:

81

Sampling time:

28 d

Details on results:

Kinetic of test substance (in %):
= 0 ... 0 after 7 day(s)
= 42 ... 54 after 14 day(s)
= 66 ... 72 after 21 day(s)
= 78 ... 84 after 28 day(s)
Kinetic of control substance (in %):
= 2 ... 5 after 7 day(s)
= 76 ... 94 after 28 day(s)

Validity criteria fulfilled:

not specified

Interpretation of results:

readily biodegradable

Executive summary:

The biodegradability of the test item was studied in a "BOD Test" that was designed for insoluble substances. The results indicate that the test item is readily biodegradable under the present test conditions. 81% of the test item degraded within a period of 28 days.

The study was classified as "reliable with restrictions".

Description of key information

The closed bottle test revealed only 5% biodegradation within 28 days (Hüls AG, 1996) but the BODIS test (draft ISO standard 10708 resulted in 81% biodegradation after 28 days (Hüls AG 1989).
In addition, there are numerous publications indicating that 1,2,3,4-tetrahydronaphthalene is biodegradable and it is used as carbon and energy source by several bacteria strains.

Key value for chemical safety assessment

Biodegradation in water:

readily biodegradable

Additional information

The closed bottle test revealed only 5% biodegradation within 28 days (Hüls AG, 1996) but the BODIS test (draft ISO standard 10708 resulted in 81% biodegradation after 28 days (Hüls AG 1989).

This difference was probably due to a much higher inoculum and test substance concentration used in the BODIS test compared to the Closed Bottle Test. The Scientific Committee on Health and Environmental Risks (SCHER) of the European Commission published an opinion on the compatibility of the ISO standard 10708 with tests on the ultimate biodegradability as imposed through annex III of the European regulation on detergents (648/2004, see attachment). The authors concluded that the ISO 10708 test is comparable in terms of the methodology to the tests on ultimate biodegradability described in Annex III of the Regulation 648/2004, and that the ISO 10708 provides an equivalent level of reliability and stringency to the international test methods on ultimate biodegradability. Therefore, the available BODIS test is regarded as key study and based on the above given arguments tetrahydronaphthalene can be considered as readily biodegradable. Moreover, there are numerous data that indicate that tetrahydronaphthalene is biodegraded by certain bacteria strains or that it is used as carbon and energy source. Therefore, tetrahydronaphthalene is expected to biodegrade well in the environment, as already concluded by the OECD SIDS evaluation (SIAM 19).