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EC number: 309-832-1 | CAS number: 101227-09-2
- Life Cycle description
- Uses advised against
- Endpoint summary
- Appearance / physical state / colour
- Melting point / freezing point
- Boiling point
- Density
- Particle size distribution (Granulometry)
- Vapour pressure
- Partition coefficient
- Water solubility
- Solubility in organic solvents / fat solubility
- Surface tension
- Flash point
- Auto flammability
- Flammability
- Explosiveness
- Oxidising properties
- Oxidation reduction potential
- Stability in organic solvents and identity of relevant degradation products
- Storage stability and reactivity towards container material
- Stability: thermal, sunlight, metals
- pH
- Dissociation constant
- Viscosity
- Additional physico-chemical information
- Additional physico-chemical properties of nanomaterials
- Nanomaterial agglomeration / aggregation
- Nanomaterial crystalline phase
- Nanomaterial crystallite and grain size
- Nanomaterial aspect ratio / shape
- Nanomaterial specific surface area
- Nanomaterial Zeta potential
- Nanomaterial surface chemistry
- Nanomaterial dustiness
- Nanomaterial porosity
- Nanomaterial pour density
- Nanomaterial photocatalytic activity
- Nanomaterial radical formation potential
- Nanomaterial catalytic activity
- Endpoint summary
- Stability
- Biodegradation
- Bioaccumulation
- Transport and distribution
- Environmental data
- Additional information on environmental fate and behaviour
- Ecotoxicological Summary
- Aquatic toxicity
- Endpoint summary
- Short-term toxicity to fish
- Long-term toxicity to fish
- Short-term toxicity to aquatic invertebrates
- Long-term toxicity to aquatic invertebrates
- Toxicity to aquatic algae and cyanobacteria
- Toxicity to aquatic plants other than algae
- Toxicity to microorganisms
- Endocrine disrupter testing in aquatic vertebrates – in vivo
- Toxicity to other aquatic organisms
- Sediment toxicity
- Terrestrial toxicity
- Biological effects monitoring
- Biotransformation and kinetics
- Additional ecotoxological information
- Toxicological Summary
- Toxicokinetics, metabolism and distribution
- Acute Toxicity
- Irritation / corrosion
- Sensitisation
- Repeated dose toxicity
- Genetic toxicity
- Carcinogenicity
- Toxicity to reproduction
- Specific investigations
- Exposure related observations in humans
- Toxic effects on livestock and pets
- Additional toxicological data
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Endpoint summary
Administrative data
Description of key information
Additional information
The long-chain aliphatic ester (LCAE) category covers mono-esters of a fatty acid and a fatty alcohol. The category contains both mono-constituent and UVCB substances. The fatty acid carbon chain lengths range is C8 - C22 (even- and un-even numbered, including saturated, unsaturated, branched and linear chains) esterified with fatty alcohols with chain lengths from C8 - C22 (even-numbered, including saturated, unsaturated, branched and linear) in varying proportions to mono-esters.
Fatty acid esters are generally produced by chemical reaction of an alcohol (e.g. myristyl alcohol, stearyl alcohol) with an organic acid (e.g. myristic acid, stearic acid) in the presence of an acid catalyst (Radzi et al., 2005). The esterification reaction is started by the transfer of a proton from the acid catalyst to the alcohol to form an alkyloxonium ion. The carboxylic acid is protonated on its carbonyl oxygen followed by a nucleophilic addition of a molecule of the alcohol to the carbonyl carbon of the acid. An intermediate product is formed. This intermediate product loses a water molecule and proton to give an ester (Liu et al., 2006; Lilja et al., 2005; Gubicza et al., 2000; Zhao, 2000). Mono-esters are the final products of the esterification.
In accordance with Article 13 (1) of Regulation (EC) No 1907/2006, "information on intrinsic properties of substances may be generated by means other than tests, provided that the conditions set out in Annex XI are met.” In particular, information shall be generated whenever possible by means other than vertebrate animal tests, which includes the use of information from structurally related substances (grouping or read-across).
Having regard to the general rules for grouping of substances and read-across approach laid down in Annex XI, Item 1.5, of Regulation (EC) No 1907/2006, whereby substances may be considered as a category provided that their physicochemical, toxicological and ecotoxicological properties are likely to be similar or follow a regular pattern as a result of structural similarity, the substances listed below are allocated to the category of LCAE.
CAS |
EC Name |
Molecular weight |
Fatty alcohol chain length |
Fatty acid chain length |
Molecular formula |
CAS 20292-08-4 (b) |
2-ethylhexyl laurate |
312.53 |
C8 |
C12 |
C20H40O2 |
CAS 91031-48-0 |
Fatty acids, C16 - 18, 2-ethylhexyl esters |
368.65; 396.7 |
C8 |
C16 - 18 |
C24H48O2; C26H52O2 |
CAS 26399-02-0 |
2-ethylhexyl oleate |
394.67 |
C8 |
C18 |
C26H50O2 |
CAS 868839-23-0 |
propylheptyl octanoate |
284.48 |
C10 |
C8 |
C18H36O2 |
CAS 3687-46-5 |
decyl oleate |
422.73 |
C10 |
C18 |
C28H54O2 |
CAS 59231-34-4 (a) |
isodecyl oleate |
422.73 |
C10 |
C18 |
C28H54O2 |
CAS 36078-10-1 |
dodecyl oleate |
450.78 |
C12 |
C18 |
C30H58O2 |
CAS 95912-86-0 |
Fatty acids, C8 - 10, C12 - 18-alkyl esters |
312.53 - 424.74 |
C12 - 18 |
C8 - 10 |
C20H40O2; C22H44O2; C26H52O2; C28H56O2 |
CAS 95912-87-1 |
Fatty acids, C16 - 18, C12 - 18-alkyl esters |
424.74 - 536.96 |
C12 - 18 |
C16 - 18 |
C28H56O2; C30H60O2; C34H68O2; C36H72O2 |
CAS 91031-91-3 |
Fatty acids, coco, isotridecyl esters |
382.66 - 410.72 |
C13 |
C12 - 18 |
C25H50O2; C27H54O2 |
CAS 85116-88-7 |
Fatty acids, C14 - 18 and C16 - 18 unsaturated, isotridecyl esters |
410.72 - 466.82 |
C13 |
C14 - 18 |
C27H54O2; C29H56O2; C31H60O2; C31H62O2 |
CAS 95912-88-2 |
Fatty acids, C16 - 18, isotridecyl esters |
438.78 - 466.83 |
C13 |
C16 - 18 |
C29H58O2; C31H62O2 |
CAS 3234-85-3 |
tetradecyl myristate |
424.74 |
C14 |
C14 |
C28H56O2 |
CAS 22393-85-7 |
tetradecyl oleate |
478.84 |
C14 |
C18 |
C32H62O2 |
CAS 101227-09-2 |
Fatty acids, C16 - 18, 2-hexyldecyl esters |
480.85; 508.90 |
C16 |
C16 - 18 |
C32H64O2; C34H68O2 |
CAS 94278-07-6 |
2-hexyldecyl oleate |
506.89 |
C16 |
C18 |
C34 |
CAS 97404-33-6 |
Fatty acids, C16 - 18, C16 - 18-alkyl esters |
480.85 - 536.97 |
C16 - 18 |
C16 - 18 |
C32H64O2; C34H68O2; C36H72O2 |
Former CAS 97404-33-6 |
Fatty acids, C12-18 (even numbered); C16-20 (even numbered) alkyl esters |
424.74 - 565.01 |
C16 - 20 |
C12 - 18 |
C28H56O2; C38H76O2 |
CAS 72576-80-8 |
isooctadecyl palmitate |
508.90 |
C18 |
C16 |
C34H68O2 |
CAS 3687-45-4 |
(Z)-octadec-9-enyl oleate |
532.92 |
C18 |
C18 |
C36H68O2 |
CAS 17673-56-2 |
(Z)-octadec-9-enyl (Z)-docos-13-enoate |
589.03 |
C18 |
C22 |
C40H76O2 |
CAS 96690-38-9 |
Fatty acids, C16 - 18, 2-octyldodecyl esters |
536.96; 565.01 |
C20 |
C16 - 18 |
C36H72O2; C38H76O2 |
CAS 93803-87-3 |
2-octyldodecyl isooctadecanoate |
565.01 |
C20 |
C18 |
C38H70O2 |
CAS 17671-27-1 |
docosyl docosanoate |
649.17 |
C22 |
C22 |
C44H88O2 |
CAS 111937-03-2 (c) |
isononanoic acid, C16 - 18 alkyl esters |
382.66; 410.72 |
C16 - 18 |
C9 |
C25H50O2; C27H54O2 |
(a) Category members subjected to the REACh Phase-in registration deadline of 31 May 2013 are indicated in bold font.
(b) Substances that are either already registered under REACh, or not subject to the REACh Phase-in registration deadline of 31 May 2013, are indicated in normal font.
(c) Surrogate substances are chemicals of structurally similar fatty acid esters. Available data on these substances are used for assessment of (eco-)toxicological properties by read-across on the same basis of structural similarity and/or mechanistic reasoning as described below for the present category.
Grouping of substances into this category is based on:
(1) common functional groups: all the members of the category are esters of a mono-functional alcohol with one carboxylic (fatty) acid chain. The fatty alcohol moiety has chain lengths from C8 - C22 (uneven/even-numbered, including saturated and unsaturated, and branched and linear chains) in varying proportions. The fatty acid moiety consists of carbon chain lengths from C8 - C22 (uneven/even-numbered) and includes saturated and unsaturated, and branched and linear chains bonded to the alcohol, resulting in mono-esters; and
(2) common precursors and the likelihood of common breakdown products via biological processes, which result in structurally similar chemicals: the members of the category result from esterification of the alcohol with the respective fatty acid(s). Esterification is, in principle, a reversible reaction (hydrolysis). Thus, the alcohol and fatty acid moieties are simultaneously precursors and breakdown products of the category members. Monoesters are hydrolysed by enzymes in the gastrointestinal tract. The rate varies depending on the acid and alcohol chain length, but is relatively slow compared with the ester bonds of triglycerides (Mattson and Volpenhein, 1969; Savary and Constantin, 1970). The hydrolysis products are absorbed via the lymphatic system and subsequently enter the bloodstream. Fatty acids can be oxidised or re-esterified and stored, depending on the need for metabolic energy. The oxidation occurs primarily via beta-oxidation, which involves the sequential cleavage of two-carbon units, released as acetyl-CoA through a cyclic series of reactions catalysed by several specific enzymes. This happens in the mitochondria and, to a lesser degree, the peroxisomes (Lehninger et al., 1993). Alternative oxidation pathways (alpha- and omega-oxidation) are available and are relevant for degradation of branched fatty acids. Unsaturated fatty acids require additional isomerization prior to entering the β-oxidation cycle. The alcohol is, in general, enzymatically oxidized to the corresponding carboxylic acid, which can then be degraded via β-oxidation (Lehninger et al., 1993). (Refer to IUCLID Section 5.3 “Bioaccumulation” and 7.3 “Toxicokinetics, metabolism and distribution” for details); and
(3) constant pattern in the changing of the potency of the properties across the category: the available data show similarities within the category in regard to physicochemical, environmental fate, ecotoxicological and toxicological properties.
a) Physicochemical properties:
The molecular weight of the category members ranges from 284.48 to 649.17 g/mol. The physical appearance is related to the chain length of the fatty acid moiety, the degree of saturation and the branching. Monoesters of short-chain and/or unsaturated and/or branched fatty acids are mainly liquid, while the long-chain fatty acids are generally solids. All the category members are non-volatile (vapour pressure: <0.0001 Pa (minimum) - 0.11 Pa (maximum)). The octanol/water partition coefficient increases with increasing fatty acid chain length, ranging from 7.67 (C8 (FA)/C12iso (FAlc.) ester)) to 20.51 (C22-monoester). The water solubility is low for all category members (< 1 mg/L or even < 0.05 mg/L).
b) Environmental fate and ecotoxicological properties:
Considering the low water solubility (< 1 mg/L or even < 0.05 mg/L) and the potential for adsorption to organic soil and sediment particles (log Koc > 5), the main compartments for environmental distribution are expected to be the soil and sediment. Nevertheless, persistency in these compartments is not expected since all members of the LCAE Category are readily biodegradable and are thus expected to be eliminated in sewage treatment plants to a high extent. Release to surface waters, and thereby exposure of sediment, is very unlikely. Thus, the soil is expected to be the major compartment of concern. Nevertheless, the category members are expected to be metabolised by soil microorganisms. Evaporation into air and the transport through the atmosphere to other environmental compartments is not expected since the category members are not volatile based on the low vapour pressure (vapour pressure: <0.0001 Pa (minimum) - 0.11 Pa (maximum)). All members of the category did not show any effects on aquatic organisms in the available acute and chronic tests representing the category members up to the limit of water solubility. Moreover, bioaccumulation is assumed to be low since the category members undergo common metabolic pathways and will be excreted or used as energy source for catabolism.
c) Toxicological properties:
The available data indicate that all the category members show similar toxicological properties. Thus, none of the category members caused acute oral, dermal or inhalation toxicity, or skin or eye irritation, or skin sensitisation. No treatment-related effects were noted up to and including the limit dose of 1000 mg/kg bw/day after repeated oral exposure in a total of 6 studies. In one study the NOAEL was set at 300 mg/kg bw/day, due to reduced food intake and weight loss observed in dams at the highest dose level. These adverse systemic effects subsequently caused impaired fertility in the dams, and reduced pup viability and body weight. However, considering all the available data the category members have a very limited potential for toxicity. The substances did not show a potential for toxicity to reproduction, fertility and development unless systemic toxicity was also evident at the same dose level. No mutagenic or clastogenic potential was observed.
The available data allows for an accurate hazard and risk assessment of the category and the category concept is applied for the assessment of environmental fate and environmental and human health hazards. Thus, where applicable, environmental and human health effects are predicted from adequate and reliable data for source substance(s) within the group, by interpolation to the target substances in the group (read-across approach), applying the group concept in accordance with Annex XI, Item 1.5, of Regulation (EC) No 1907/2006. In particular, for each specific endpoint the source substance(s) structurally closest to the target substance is/are chosen for read-across, with due regard to the requirements for adequacy and reliability of the available data. Structural similarities and similarities in properties and/or activities of the source and target substance are the basis of read-across.
A detailed justification for the grouping of chemicals and read-across is provided in the technical dossier (see IUCLID Section 13).
The terrestrial toxicity data of the LCAE category members are presented in the following table.
Terrestrial toxicity data of the LCAE category members
CAS |
Toxicity to soil macroorganisms except arthropods |
Toxicity to terrestrial arthropods |
Toxicity to terrestrial plants |
Toxicity to soil microorganisms |
3687-46-5 (b) |
RA: CAS 95912-86-0 RA: CAS 93803-87-3 |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
59231-34-4 (a) |
RA: CAS 95912-86-0 RA: CAS 93803-87-3 |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
36078-10-1 |
RA: CAS 95912-86-0 RA: CAS 93803-87-3 |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
95912-86-0 |
NOEC (56 d): 500 mg/kg soil dw |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
95912-87-1 |
RA: CAS 95912-86-0 RA: CAS 93803-87-3 |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
91031-91-3 |
RA: CAS 95912-86-0 RA: CAS 93803-87-3 |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
85116-88-7 |
RA: CAS 95912-86-0 RA: CAS 93803-87-3 |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
95912-88-2 |
RA: CAS 95912-86-0 RA: CAS 93803-87-3 |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
3234-85-3 |
RA: CAS 95912-86-0 RA: CAS 93803-87-3 |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
22393-85-7 |
RA: CAS 95912-86-0 RA: CAS 93803-87-3 |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
101227-09-2 |
RA: CAS 93803-87-3 |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
97404-33-6 |
RA: CAS 95912-86-0 RA: CAS 93803-87-3 |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
Former CAS 97404-33-6 |
RA: CAS 95912-86-0 RA: CAS 93803-87-3 |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
72576-80-8 |
RA: CAS 95912-86-0 RA: CAS 93803-87-3 |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
3687-45-4 |
RA: CAS 95912-86-0 RA: CAS 93803-87-3 |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
17673-56-2 |
RA: CAS 95912-86-0 RA: CAS 93803-87-3 |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
96690-38-9 |
RA: CAS 93803-87-3 |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
93803-87-3 |
NOEC (56 d): ≥ 1000 mg/kg soil dw |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
17671-27-1 |
RA: CAS 95912-86-0 RA: CAS 93803-87-3 |
Waiving based on CSA |
Waiving based on CSA |
Weight of Evidence (WoE)
|
(a) Category members subjected to the REACh Phase-in registration deadline of 31 May 2013 are indicated in bold font.
(b) Substances that are either already registered under REACh, or not subject to the REACh Phase-in registration deadline of 31 May 2013, are indicated in normal font. Lack of data for a given endpoint is indicated by “--“.
Exposure of the soil compartment is generally considered to be low. Even if exposed to the soil the LCAE category members are readily biodegradable indicating that they will not be persistent in the environment. Indirect exposure via irrigation or atmospheric transport is considered to be negligible based on the physico-chemical properties of the LCAE category members (water solubility:< 1 mg/L or even < 0.05 mg/L;vapour pressure: <0.0001 Pa (minimum) - 0.11 Pa (maximum)).
Experimental data investigating the toxicity of the LCAE category members to earthworms are available for the two representative category members fatty acids, C8-10, C12-18-alkyl esters (CAS 95912-86-0) and 2-octyldodecyl isooctadecanoate (CAS 93803-7-3) covering the variability of the category with different alcohol and representative fatty acid chain lengths. Testing of the toxicity on earthworm evaluates the exposure to the test substance via soil pore water, surface contact as well as by ingestion of soil particles. Due to the high adsorption potential (log Koc > 5), long-term testing was considered to be relevant to investigate further the effects of the substance on terrestrial organisms. The available studies according to OECD 222 were performed for the category members fatty acids, C8-10, C12-18-alkyl esters (CAS 95912-86-0) and 2-octyldodecyl isooctadecanoate (CAS 93803-7-3). Fatty acids, C8-10, C12-18-alkyl esters is characterized by a short-chain fatty acid (C8-10) and fatty alcohol (C12-14) covering the lower end of the category. 2-octyldodecyl isooctadecanoate was selected to cover the upper end of the category since it is structurally characterized by a long-chain fatty acid (C18iso) and a branched fatty alcohol component with a chain length of C20. Therefore, most of the data gaps can be covered by interpolation. Both substances are also covering different routes for possible uptake of the substance. Dermal uptake via pore water is not considered to be a relevant exposure pathway based on the very low water solubility. However, the smallest substance of the category (Fatty acids, C8-10, C12-18-alkyl esters) represents a worst case for the uptake via dermal absorption since the substance is expected to be the most water soluble of all the category members. The water solubility is negatively correlated with the C-chain lengths of the fatty acid and fatty alcohol (Lide, 2005). Whereas, 2-octyldodecyl isooctadecanoate is representative as one of the category members with the highest potential for adsorption to soil particles which can be taken up via ingestion (log Koc: 10.49; Müller, 2011). Thus, the two main routes of exposure for terrestrial organisms are covered by studies with the two representative category members. The study with the read-across substance fatty acids, C8-10, C12-18-alkyl esters resulted on a NOEC (56 d) of 500 mg/kg dw whereas the available study with 2-octyldodecyl isooctadecanoate resulted in no effects on reproduction with a NOEC (56 d) ≥ 1000 mg/kg soil dw. After absorption, the LCAE category members are expected to be enzymatically hydrolyzed by carboxylesterases yielding to the corresponding alcohol and fatty acid. QSAR estimations using BCFBAF v3.0 support the expected rapid biotransformation of this substance with BCF/BAF values of 0.89 - 14.07 and 0.89 - 314 L/kg were obtained, respectively. The metabolism of the hydrolysis products is well established and not of concern in terms of bioaccumulation (for further information see chapter 5.3 of the technical dossier). Summarizing, the LCAE category members are expected to be rapidly hydrolyzed to the respective fatty acid and fatty alcohol. Both hydrolysis products are supposed to be satisfactory metabolized in terrestrial organisms. Therefore, the potential for bioaccumulation is low. Available acute and chronic aquatic toxicity tests to fish, invertebrates, algae and microorganisms showed no adverse effects occurred in the range of the water solubility of the LCAE category members (< 1 mg/L or even < 0.05 mg/L). These results support the assumption that the LCAE category members are of low toxicity to terrestrial organisms.
The available data for toxicity to aquatic microorganisms for the LCAE category members supports the determination of a lack of toxicity to soil microorganisms. No inhibition of respiration rate of aquatic microorganisms was observed in any of the available studies for the LCAE category members. The Guidance Document (ECHA, 2012, page 122) states that a test on soil microbial activity will only be additionally necessary for a valid PNEC derivation if inhibition of sewage sludge microbial activity has occurred and this is clearly not the case. This is supported by further evidence from literature data. This data showed that soil microorganism communities are well capable of degrading fatty acid esters (Hita et al., 1996 and Cecutti et al., 2002) and use them as energy source (Banchio & Gramajo, 1997). Based on the available information, effects on soil microorganisms are not expected to be of concern, and consequently, no further testing is required.
In conclusion the LCAE category members are of low toxicity to terrestrial organisms based on all available data.
A detailed reference list is provided in the technical dossier (see IUCLID, section 13) and within the CSR.
Information on Registered Substances comes from registration dossiers which have been assigned a registration number. The assignment of a registration number does however not guarantee that the information in the dossier is correct or that the dossier is compliant with Regulation (EC) No 1907/2006 (the REACH Regulation). This information has not been reviewed or verified by the Agency or any other authority. The content is subject to change without prior notice.
Reproduction or further distribution of this information may be subject to copyright protection. Use of the information without obtaining the permission from the owner(s) of the respective information might violate the rights of the owner.
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