Nonan-1-ol

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

biodegradation in water: screening test, other

Remarks:

(BOD5 test)

Type of information:

experimental study

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

study well documented, meets generally accepted scientific principles, acceptable for assessment

Remarks:

Non-guideline study using acclimated inoculum. Whilst pre-acclimation would normally be considered a major methodological deficiency, in the case of the aliphatic alcohols which are naturally occurring in the environment and also produced by microorganisms, pre-acclimation of the culture is not considered to significantly affect the test outcome.

Principles of method if other than guideline:

COD Method: other: APHA 1980

Details on results:

47.9% degradation after 5 days (% ThOD)

Parameter:

BOD5*100/ThOD

Value:

47.9 other: % ThOD

The primary purpose of this study was to determine a quantitative structure-biodegradability relationship for a series of alcohols.

Interpretation of results:

not readily biodegradable

Conclusions:

The test material is not considered to be readily biodegradable based on a BOD5/ThOD ratio of <0.5.

Reference 2

Endpoint:

biodegradation in water: screening test, other

Type of information:

read-across from supporting substance (structural analogue or surrogate)

Adequacy of study:

weight of evidence

Justification for type of information:

1. HYPOTHESIS FOR THE CATEGORY APPROACH
The hypothesis is that the category members have similar structures and properties (very rapid biodegradability), which are consistent across the category (Scenario 6 in the RAAF). The consistency of this property across the category is discussed in the endpoint summary.

2. SOURCE AND TARGET CHEMICAL(S) (INCLUDING INFORMATION ON PURITY AND IMPURITIES)
Please refer to the test material identity information within each endpoint study record.

The long chain linear aliphatic alcohol Category has at its centre an homologous series of increasing carbon chain length alcohols. The category members are structurally very similar. They are all primary aliphatic alcohols with no other functional groups. The category members are linear or contain a single short-chain side-branch at the 2-position in the alkyl chain, which does not significantly affect the properties (‘essentially linear’). The category members have saturated alkyl chains or contain a small proportion of naturally-occurring unsaturation(s) which does not significantly affect the properties. The branched and unsaturated structures are considered to have such similar properties that their inclusion in the category is well justified.
Impurities: Linear and/or ‘essentially linear’ long chain aliphatic alcohols of other chain lengths may be present. These are not expected to contribute significantly to the properties in respect of this endpoint due to consistent properties (see point 3).
There are no impurities present at or above 1% which are not category members or which would affect the properties of the substance.

3. CATEGORY JUSTIFICATION
The category members are structurally very similar (see point 2) and are biochemically very similar. The metabolic synthesis and degradation pathways are well established. This Category is associated with a consistency and predictability in the physicochemical, environmental, and toxicological property data across its members.

The consistency of observations in this property across the range of chain lengths covered by this Category is described in the Endpoint Summary and in the Category Report attached in Section 13.

In this registration, the information requirement is interpolated based on read-across from octan-1-ol and decan-1-ol, with shorter and longer chain length within the chemical category, providing evidence of consistency in behaviour irrespective of variation in physico-chemical properties of specific category member substances.

4. DATA MATRIX
A data matrix for the C6-24 alcohols Category is attached in Section 13.

Reason / purpose for cross-reference:

read-across source

Reason / purpose for cross-reference:

read-across source

Reason / purpose for cross-reference:

read-across source

Reason / purpose for cross-reference:

read-across source

Parameter:

% degradation (CO2 evolution)

Value:

74.6

Sampling time:

28 d

Remarks on result:

other: C10

Parameter:

% degradation (DOC removal)

Value:

88

Sampling time:

30 d

Remarks on result:

other: C10

Parameter:

% degradation (CO2 evolution)

Value:

>= 64 - <= 79

Sampling time:

28 d

Remarks on result:

other: C7-C9

Parameter:

% degradation (CO2 evolution)

Value:

92

Sampling time:

28 d

Remarks on result:

other: C8

Description of key information

Readily biodegradable: 74.6 - 77.9% (CO2) in 28 days (OECD 301B; not GLP) based on weight of evidence from read-across studies.

Key value for chemical safety assessment

Biodegradation in water:

readily biodegradable

Additional information

Only one study is available with nonan-1-ol, for which the outcome is not reliable, but there is considerable weight of evidence from reliable studies conducted with neighbouring chain length alcohols within the Category.

A reliable study (Federle, 2009), conducted according to an appropriate test protocol (OECD 301B), but not conducted according to GLP, determined the C8 and C10 analogues, octan-1-ol and decan-1-ol, to be readily biodegradable (77.9% and 74.6% CO2 evolution in 28 days), meeting the ten day window. Trichloromethane was used as a solubilising agent in this study. The solvent was then evaporated under a gentle stream of N₂ gas to deposit the test material as a film on the walls of the vessel.

This study (Federle, 2009), using a methodology with appropriate loading method for the low solubility of the substances, was carried out with a range of linear saturated alcohols from four carbon chain length (C4) to twenty-two carbon chain length (C22).

These results are significant and fit for purpose even though the study was not conducted to GLP. The study gave results of 76.1% (C4), 77.7% (C6), 77.9% (C8), 74.6% (C10), 69.0% (C12), 82.2% (C14), 82.4% (C16), 95.6% (C18), 88.4% (C20) and 87.9% (C22) in 28 days. All were readily biodegradable, meeting the ten-day window.

This evidence is presented as weight of evidence together with degradation of 92% in 28 days for octan-1-ol in a reliable, GLP-compliant test using ISO standard methodology similar to OECD 310 (P&G, 1996).

59% degradation was reported in a study using the modified Sturm test methodology (Huntingdon Life Sciences, 1996).

53 -54% degradation based on O2 consumption was reported in a reliable study of Alcohols, C7-9 (Miller, 1984) in accordance with OECD 301D methodology.

In addition to the reliable standard protocol ready biodegradation studies discussed above, a 5-day biochemical oxygen demand study is available for nonan-1-ol (Vaishnav 1987). REACH Guidance (Chapter R7b) states the following regarding this type of test:

"Information on the 5-day biochemical oxygen demand (BOD5) can be used for classification purposes only when no other measured degradability data are available. Thus, priority is given to data from ready biodegradability tests and from simulation studies regarding degradability in the aquatic environment. The BOD5 test is a traditional biodegradation test that is now replaced by the readybiodegradability tests. Therefore, this test should not be performed today for assessment of the ready biodegradability of substances. Older test data may, however, be used when no other degradability data are available".

This BOD5 study is therefore selected as supporting studies. The test indicates not readily biodegradable based on a BOD5/ThOD ratio of 0.479.

It is quite normal to observe some inter-laboratory variation in screening studies, particularly for substances where solubility limits may be a factor in degradation rates under the conditions of the testing. Due to the very diluted nature of the inoculum and its limited size, it may sometime happen that no degradation-competent microorganisms are present in a particular inoculum. This is evidenced by the variable mineralisation levels seen for standard reference substances under the conditions of OECD 301 (e.g. glucose, 55-90%; benzoates 61-95%) in studies collated by AISE/CESIO [AISE/CESIO company data, and the 'Study on the possible problems for the aquatic environment related to surfactants in detergents' (WRc Ref EC4294, May 1997)].

In the case where multiple reliable studies exist showing a range of extent of biodegradation in the course of standard tests, the normal approach is to base the interpretation on the higher degradation results, this is in line with ECHA guidance on information requirements and chemical safety assessment. An important piece of additional evidence to consider is the availability of ready biodegradation data from a series of tests conducted at the same laboratory at the same time, to examine degradability throughout the series of linear alcohols from C4-C22. Whilst at the time of the study by Federle (2009), the laboratory was not GLP-certified, the data are reliable and consistent throughout the homologous series. In this study (Federle, 2009) octan-1-ol (and all other chain lengths studied) was found to be readily biodegradable.

The conclusion of ready biodegradability is consistent with evidence of rapid metabolism of long-chain fatty alcohols in fish, mammals and microorganisms(see IUCLID Sections 5.3.1, 7.1 and 6.1.4).

For these reasons, the lower degradation levels shown for nonan-1-ol in the BOD5 test (Vaishnav, 1987) and for the read-across substances in the Vista, 1994 and Huntingdon Life Sciences, 1996a and Miller, 1984 studies are not selected as Key.

There are also two studies for the read for which summary reports only are available. There is insufficient information reported to assess the validity of these tests. A summary report of a ready biodegradability study reports the substance to be readily biodegradable (65-77% in 30 days) (Henkel, 1999, RDA-Blok-test method). An inherent biodegradability test conducted according to US EPA OPPTS guideline found the substance to be inherently biodegradable based on 60% biodegradation (Vista, 1994).

A non-standard study published by Yonezawa and Urushigawa (1979) determined the reaction rate of octan-1-ol in the supernatant of a study culture. The half-life was found to be 1.9 hours.

>75% biodegradability under anaerobic conditions has also been demonstrated for octan-1 -ol (Shelton and Tiedje, 1984).

Discussion of trends in the Category of C6-24 linear and essentially-linear aliphatic alcohols:

Many biodegradation assays have been carried out on this family of alcohols. Studies generated on single carbon chain length alcohols for tests that conform most closely to ready test biodegradability methods (OECD 301 series) show that alcohols with chain lengths up to C22 are readily biodegradable. In all cases the inoculum was not acclimated. Older reliable data suggest that chain lengths above C18 are not readily biodegradable, however those studies used loading techniques which, while in general still reliable, did not make allowance for the reduced bioavailability caused by the low water solubility of these longest chain substances. Where the substances are introduced into the test vessels by coating onto the flask, very rapid biodegradation was confirmed at all chain lengths tested.

In the older supporting tests, alcohols with chain lengths up to C18 are readily biodegradable. At carbon chain lengths ≤ 14, most tests showed that pass levels for ready biodegradation were reached within the 10 day window. Chain lengths of C16-18 achieved ready test pass levels, but not within the 10 day window. The one test on a single carbon chain length greater than C18 (using docosanol) showed degradation of 37%.

Tests which allowed adaptation are considered to have significant methodological deficiencies in terms of REACH requirements for the present purpose, and are accordingly considered to be Klimisch reliability 3: Invalid. However these also consistently demonstrate extensive biodegradability. Aliphatic alcohols occur naturally in the environment and environmental organisms will be acclimated.

Reliable studies for decanol and tetradecanol that show low levels of degradation are considered to be unexplained outliers. It is usual in the interpretation of such data to take the highest levels of degradation as the key study.

Federle (2009) conducted ready biodegradation screening tests on even-numbered saturated single chain length alcohols (C6-C22) using an appropriate test method (OECD 301B). Although, the test was not conducted in compliance with GLP, the study was found to be consistent with other available data, reliable and acceptable for environmental assessment. All tests substances were found to behave in a similar way. The substances were found to be readily biodegradable meeting the ten day window after a brief lag period. A separate test using the same methodology has confirmed the ready biodegradability result, meeting the ten-day window, at the upper end of the carbon number range (docosan-1-ol) in a GLP-compliant study (Flach, 2012).

Some variability is seen in the ultimate percentage degradation over the course of the study (see Table below). It is quite normal to observe some inter-laboratory variation in screening studies, particularly for substances where solubility limits may be a factor in degradation rates under the conditions of the testing. As discussed above, due to the very diluted nature of the inoculum and its limited size, it may sometime happen that no degradation-competent microorganisms are present in a particular inoculum. This is evidenced by the variable mineralisation levels seen for standard reference substances under the conditions of OECD 301. In the case where multiple reliable studies exist showing a range of extent of biodegradation in the course of standard tests, the normal approach is to base the interpretation on the higher degradation results, this is in line with ECHA guidance on information requirements and chemical safety assessment, and consistent with the availability of ready biodegradation data from a series of tests conducted at the same laboratory at the same time, to examine degradability throughout the series of linear alcohols from C6-C22. Whilst at the time of the study (P&G, 2009), the laboratory was not GLP-certified, the data are reliable and consistent throughout the homologous series. In this study (Federle, 2009) and all other chain lengths studied were found to be readily biodegradable.

Biodegradation under anaerobic conditions

The anaerobic biodegradability of a range of chain lengths within the category has been investigated (C8, C16 alcohols (two studies), and C16-18 and C18 unsaturated alcohols). All test substances were anaerobically degradable. Results from available studies are presented in the table below.

Biodegradation by algae

Rapid degradation in water is indicated by the difficulties encountered in aquatic toxicity tests (chronic Daphnia reproduction) for long chain aliphatic alcohols (Section 6.1.4). Alcohols in the range C10-C15 were found to be rapidly removed from the test medium. This was attributed to metabolism by algae present as a food source in tests, and in later stages of the 21-day tests to bacterial degradation by microbes adsorbed onto the carapace of the test daphnids, despite daily cleaning of the animals.

Natural occurrence

It is important for context to note the findings from studies in the EU and US which consistently show that anthropogenic alcohols in the environment are minimal compared to the level of natural occurrence. Using stable isotope signatures of fatty alcohols in a wide variety of household products and in environmental matrices sampled from river catchments in the United States and United Kingdom, Mudge et al.(2012) estimated that 1% or less of fatty alcohols in rivers are from waste water treatment plant (WWTP) effluents, 15% is fromin situproduction (by algae and bacteria), and 84% is of terrestrial origin. Further, the fatty alcohols discharged from the WWTP are not the original fatty alcohols found in the influent. While the compounds might have the same chain lengths, they have different stable isotopic signatures (Mudgeet al., 2012).

In conclusion, the environmental impact of these studies is that it has confirmed that the fatty alcohols entering a sewage treatment plant (as influent) are partly derived from detergents, but these are not the same alcohols as those in the effluent which arise fromin-situbacterial synthesis. In turn, the fatty alcohols found in the sediments near the outfall of the WWTP are derived from natural synthesis and are not the same alcohols as those in the effluent.

Ready biodegradation data on single constituent alcohols

CAS	Chemical Name	Comment	Method	Result % degradation	Result 10 day window	Reliability	Reference
111-27-3	1-Hexanol		301B	77.7% in 28 days at 17 mg/L	69.8%	2	Federle 2009
111-27-3	1-Hexanol		OECD 301-D	77% in 30 days at 2 mg/L 61% in 30 days at 5 mg/L	>60% in 14 days	2	Richterich, 2002a
111-27-3	1-Hexanol		Non-standard	- half life of 8.7 hours	-	2	Yonezawa and Urushigawa 1979
111-87-5	1-Octanol		301B	77.9% in 28 days at 18.8 mg/L	79.2%	2	Federle 2009
111-87-5	1-Octanol		ISO ring test (CO2 headspace biodegr. test)	92% in 28 days at 20 mg/L	>60%	2	Procter & Gamble, 1996
111-87-5	1-Octanol		OECD 301-B	59 % in 29 days at 10 mgC/L	-	2	Huntingdon Life Sciences Ltd. 1996a
111-87-5	1-Octanol		Non-standard	- half life of 1.9 hours	-	2	Yonezawa and Urushigawa 1979
112-30-1	1-Decanol			74.6% in 28 days at 15.1 mg/L	68.6%	2	Federle 2009
112-30-1	1-Decanol		301-D	88% in 30 days at 2 mg/L	>60%	2	Richterich, 2002c
112-30-1	1-Decanol		301-B	29 % after 29 day(s) at 10 mg/L COD	-	2	Huntingdon Life Sciences Ltd. 1996b
112-53-8	1-Dodecanol		301B	69% in 28 days at 15.4 mg/L	63%	2	Federle 2009
112-53-8	1-Dodecanol	Supporting	301-D	79% in 28 days at 2 mg/L	>60% in 14 days	1	Werner, 1993
112-72-1	1-Tetradecanol		301B	82.2% in 28 days at 15.9 mg/L	77.2%	2	Federle 2009
112-72-1	1-Tetradecanol		BODIS ~ISO 10708	92% in 28 days at 100 mg/L COD	>60%	1	Henkel, 1992d
112-72-1	1-Tetradecanol		301-B	28 % after 28 day(s) at 25.4 mg/L	-	1	Mead 1997b
36653-82-4	1-Hexadecanol		301B	82.4% in 28 days at 15.3 mg/L	75.2%	2	Federle 2009
36653-82-4	1-Hexadecanol		301B	62% after 28 days at 17.1 mg/L	<60%	1	Mead, 1997c
36653-82-4	1-Hexadecanol		BODIS	76 % after 28 day(s) at 100 mg/L COD	<60% after 14 d	2	Henkel KGaA 1992a
112-92-5	1-Octadecanol		301B	95.6% in 28 days at 14.5 mg/L	90.2%	2	Federle 2009
112-92-5	1-Octadecanol	Supporting	301D	38% in 29 days at 5 mg/L 69% in 29 days at 2 mg/L	<60%	1	Henkel, 1992f
629-96-9	1-Eicosanol		301B	88.4% in 28 days at 15.6 mg/L	83.4%	2	Federle 2009
661-19-8	1-Docosanol		301B	87.5% in 28 days at 20 mg/L	75.6%	1	Flach, 2012
661-19-8	1-Docosanol		301B	87.9% in 28 days at 15.3 mg/L	83%	2	Federle 2009
661-19-8	1-Docosanol		301B	37% after 28 days at 12.4 mg/L	<60%	1	Mead, 2000

 

Anaerobic degradation of alcohols

CAS	Chemical name	Comment	Method	Source of sludge	Concentration of test substance	Duration	% degradation at end of test	Reliability	Reference
111-87-5	1-Octanol		Serum bottle, gas production + GC analysis	1^oor 2^odigesters	50µg/ml	8 weeks	>75%	2	Sheltonand Tiedje, 1984
36653-82-4	1-Hexadecanol		Batch test using^14C labelled test material	Municipal digester sludge fortified with activated sludge	1 mg/L	28 days	90%	2	Nuck and Federle, 1996
36653-82-4	1-Hexadecanol		Batch test using^14C labelled test material	Municipal sewage digester	10 mg/L	28 days	97%	2	Steber and Wierich, 1987
68002-94-8	Alcohols, C16-18 and C18 unsaturated	Supporting	ECETOC screening test	Municipal sewage digester	50 mg/L	8 weeks	89%	2	Steberet al. 1995

A study by Rorije et al. (1998) on structural requirements for anaerobic biodegradation of organic chemicals is relevant. The study used a computer-automated structure evaluation program (MCASE) to analyse rates of aquatic anaerobic biodegradation of a set of diverse organic compounds, and developed a predictive model. Primary alcohols were one of the most important fragments linked to biodegradability (biophore). The authors discuss how the presence of a biophore indicates a possible site of attack for microbes to follow a metabolic pathway for anaerobic biodegradation.

Biodegradation in STP-simulation tests

Other recent data on ethoxylated alcohols also suggest that the rate of degradation could be higher than usually assigned to readily-biodegradable substances. In an OECD 303A study of the fate of alcohol ethoxylate homologues in a laboratory continuous activated sludge unit (Wind,et al., 2006) useful data about the properties and environmental exposures of alcohols are presented, although the paper describes mainly the properties of alcohol ethoxylates (AE). The waste water organisms were exposed principally to ethoxylates, but the alcohols would be generated by the degradation of the ethoxylates. The test substance comprised a 2:1 mixture of two commercial alcohol ethoxylate surfactants with chain lengths of C12-C15 (odd and even numbered) and C16-C18 (even numbered), respectively. The test substance was dosed at a concentration of 4 mg/L in the influent.

 

Results are shown in the table below:

Removal of alcohols during an activated sludge test on alcohol ethoxylates

Alcohol	Conc in effluent ng/L	Conc in sludge µg/g	%removal
C12	18	0.6	98.6
C13	21	0.7	99.5
C14	5.5	0	99.6
C15	2.9	1.1	99.8
C16	1.6	0.01	99.5
C18	58	0.7	99.1
Total	130	2	99.4

 

This shows that most of the alcohol which does not degrade (itself a small amount) was found in the solids in recovery at the end of the study.This study is important in that it indicates that the extent of removal of alcohols is high, from an exposure route that can realistically be anticipated based on the known life cycle.

References:

EU Commission, DGIII, Study on the possible problems for the aquatic environment related to surfactants in detergents, WRc, EC 4294, February, 1997

Flach, F., 2012. Biodegradability in the CO2-evolution test according to OECD 301b (July 1992). Hydrotox laboratory, report number 737, company study number 8571, Sasol, 2 May 2012.

Federle (2009). Ready Biodegradability Test, The Procter and Gamble Co., Study number 65522, 27^thApril 2009

Mudge, S.M, Deleo, P.C., Dyer, S.D. (2012). Quantifying the anthropogenic fraction of fatty alcohols in a terrestrial environment. Environmental Toxicology and Chemistry, Vol. 31, No. 6, pp. 1209–1222.

Nuck, B.A. and Federle, T.W. 1996. Batch test for assessing the mineralization of 14C-radiolabeled compounds under realistic anaerobic conditions. Environ. Sci.. 30:12, 3597-3603.

Rorije E, Peunenburg WJGM, Klopman G (1998) Structural requirements for anaerobic biodegradation of organic chemicals: A fragment model analysis. Environmental Toxicology and Chemistry, Vol. 17, No. 10, pp. 1943 -1950.

Shelton, D.R. and Tiedje, J.M. 1984. General method for determining anaerobic biodegradation potential. Applied and Environmental Microbiology 850-857.

Steber, J., Herold, C.P. and limia, J.M. 1995. Comparative evaluation of anaerobic biodegradability of hydrocarbons and fatty derivatives currently used as drilling fluids. Chemosphere 31:4, 3105-3118.

Steber, J. and Wierich, P. 1987. The anaerobic degradation of detergent range fatty alcohol ethoxylates. Studies with 14C-labelled model surfactants. Water Research. 21:6, 661-667.

Wind, T., R.J. Stephenson, C.V. Eadsforth, A. Sherren, R. Toy. (2006) Determination of the fate of alcohol ethoxylate homologues in a laboratory continuous activated sludge unit. Ecotox and Environ Safety, 64: 42-60.

Richterich, K. 2002a. 1-Hexanol: Ultimate biodegradability in the closed bottle test.Final report R 0200259.

Procter & Gamble. 1996. Final report: ISO ring test CO2 headspace biodegradation test. Study ECM ETS 554/02.

Huntingdon Life Sciences Ltd.(HLS).1996a. Report No. 96/KAS217/0325.

Richterich, K. 2002c.Final report R 0200257.

Huntingdon Life Sciences Ltd.(HLS).1996b. Report No. 96/KAS223/0327.

Richterich. 1993. 1-Dodecanol: Aerobic biodegradation: Closed bottle test. Biological Research and Product Safety/Ecology: Unpublished results; test substance registration no. SAT 910724, Henkel KGaA; Report No. RE 920247 (With English summary report no. R9901416)

Henkel KGaA.1992d.  Report No. 920026 (test substance registration no. SAT 910723, test run no. 118).5 Marz 1992.

Mead, C. 1997b. Safepharm Laboratories, SPL Project Number 140/598.

Mead, C. 1997c. Safepharm Laboratories, SPL Project Number 140/543.

Henkel KGaA. 1992a.Biological Research and Product Safety/Ecology: Report No. RE 920102; test substance registration No. SAT 910721, test run No. 120.26 Juni 1992.

Henkel KGaA.1992f. Report No.RE920246, 18 December 1992.

Mead, C. 2000. Safepharm Laboratories, SPL Project Number 140/1002.