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EC number: 692-946-1
CAS number: 649747-80-8
The Short Chain Alcohol Esters (SCAE C2-C8) category covers esters from
a fatty acid (C8-C29) and a C2-C8 alcohol (ethanol, isopropanol,
butanol, isobutanol, pentanol, iso-pentanol, hexanol, 2-ethylhexanol or
octanol). This category includes both well-defined mono-constituent
substances as well as related UVCB substances with varying fatty acid
Fatty acid esters are generally produced by chemical reaction of an
alcohol (e.g. isopropanol) with an organic acid (e.g. stearic acid) in
the presence of an acid catalyst (Radzi et al., 2005). The
esterification reaction is started by a transfer of a proton from the
acid catalyst to the acid to form an alkyloxonium ion. Acid is
protonated on its carbonyl oxygen followed by a nucleophilic addition of
a molecule of the alcohol to a carbonyl carbon of 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). Esters are the final product of 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
The rationale for grouping the substances in the SCAE C2-C8 category is
based on similarities in physicochemical, ecotoxicological and
In this particular case, the similarity of the SCAE C2-C8 category
members is justified, in accordance with the specifications listed in
Regulation (EC) No. 1907/2006 Annex XI, 1.5
Grouping of substances and read across, based on representative
molecular structure, physico-chemical properties, tox-, ecotoxicological
profiles, supported by a robust set of experimental data and QSAR
calculations. There is no convincing evidence that any one of these
chemicals might lie out of the overall profile of this category,
Grouping of substances into this category is based on:
• Similar/overlapping structural features or functional groups:
All category members are monoesters of alcohols (C2-C8) and fatty acids
(C8-C29), with 13 to 32 carbons in total.
• Common precursors and the likelihood of common
breakdown products via biological processes: All
category members are subject to enzymatic hydrolysis by pancreatic
lipases (Mattson and Volpenhein, 1972; and references therein). The
resulting free fatty acids and alcohols are absorbed from the intestine
into the blood stream. Fatty acids are either metabolised via the
beta-oxidation pathway in order to generate energy for the cell or
reconstituted into glyceride esters and stored in the fat depots in the
body. The alcohols are metabolised primarily in the liver through a
series of oxidative steps, finally yielding carbon dioxide (Berg et al.,
• Similar physico-chemical properties: The log
Kow and log Koc values of all category members are high (log Kow > 4,
log Koc > 3), increasing with the size of the molecule. The substances
are poorly soluble in water and have low vapour pressure.
• Common properties for environmental fate &
eco-toxicology: Based on experimental data, all substances (all
substances to be registered and read-across substances used for
environmental fate and ecotoxicology) are readily biodegradable and do
not show toxic effects up to the limit of water solubility.
• Common levels and mode of human health related
effects: All available experimental data indicate that the members of
the SCAE C2-C18 category are not acutely toxic, are not irritating to
the skin or to the eyes and do not have sensitizing properties. Repeated
dose toxicity was shown to be low for all substances. None of the
substances showed mutagenic effects, and toxicity to reproduction was
low throughout the category.
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 SCAE C2-C8.
Members of the SCAE C2-C8 Category:
Alcohol Carbon No.
Fatty acid Carbon No.
Fatty acids, essential, ethyl esters
14 - 22
16 - 24
Fatty acids, C16-18, isopropyl esters
16 - 18
19 - 21
Fatty acids, lanolin, isopropyl esters
10 - 29
13 - 32
Fatty acids, tall-oil, butyl esters
Fatty acids, C16-18, Bu esters
20 - 22
Fatty acids, C16-18 and C18-unsatd., Bu esters
Fatty acids, C16-18 and C18 unsatd. branched and linear, butyl esters
Fatty acids, C16-18, iso-Bu esters
Fatty acids, C16-18 and C18-unsatd., iso-Bu esters
Isopenthyl laurate Dodecanoic acid, 2-methyl butyl ester
Isopentyl decanoate and octanoate
8 - 10
13 - 15
Dodecanoic acid, hexyl ester
Dodecanoic acid, isooctyl ester
Fatty acids, C8-10, 2-ethylhexyl esters
Fatty acids, C8-16, 2-ethylhexyl esters
12 - 14
2 -ethylhexyl palmitate
2-Ethyl hexyl Stearate
Fatty acids, coco, 2-ethylhexyl esters
12 - 18
20 - 26
Fatty acids, C16-18, 2-ethylhexyl esters
24 - 26
Fatty acids, C16-18 and C18-unsatd., 2-ethylhexyl esters
(a) Category members subject to registration are indicated in bold font.
(b) Substances not subject to registration are indicated in normal font.
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 of 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. For a
detailed review of the data matrix please refer to the category
justification attached in section 13 in IUCLID.
Environmental fate and pathways
Partitioning of substances into the different environmental compartments
depends mainly on their physico-chemical properties. Since members of
the SCAE C2-C8 category are poorly soluble in water, not volatile, and
have high adsorption potential, they are not expected to be found in the
air or water compartments. If released in surface waters, the substances
would probably partition from the water phase to the sediment. Based on
physico-chemical properties, the main target compartments for SCAE C2-C8
category members would thus be soil and sediment. However, the
substances are readily biodegradable and highly sorptive, based on
calculated estimation, 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 therefore very unlikely. Accumulation
into organisms is not expected for members of the SCAE C2-C8 category,
since they can be digested by common metabolic pathways, as dietary fats
(Berg et al., 2002; Mattson and Volpenheim, 1972; Tocher, 2003).
The fate of the chemicals is also influenced by (bio-)chemical processes
they may undergo in the environment. Members of the SCAE C2-C8 category
(all substances to be registered and read-across substances used for
environmental fate and ecotoxicology) are readily biodegradable and are
therefore expected to be rapidly eliminated from the environment. They
are not likely to be degraded by abiotic processes. Hydrolysis and
photodegradation are not relevant, since the substances are not expected
to be present in the water and air compartments. Additionally, estimated
hydrolysis rates are very low at environmental conditions.
In conclusion, SCAE C2-C8 category members are expected to be found
mainly in the soil compartment, where they are expected to be rapidly
degraded by microorganisms.
Berg, J.M., Tymoczko, J.L. and Stryer, L., 2002, Biochemistry, 5thedition,
W.H. Freeman and Company
Gubicza, L., Kabiri-Badr, A., Keoves, E., Belafi-Bako, K. (2000):
Large-scale enzymatic production of natural flavour esters in organic
solvent with continuous water removal. Journal of Biotechnology 84(2):
– Hazardous Substances Data Bank, Toxnet Home, National Library of
Medicinehttp: //toxnet. nlm. nih. gov/cgi-bin/sis/htmlgen?HSDB
Lilja, J. et al. (2005). Esterification of propanoic acid with
ethanol, 1-propanol and butanol over a heterogeneous fiber catalyst.Chemical
Engineering Journal, 115(1-2): 1-12.
Liu, Y. et al. (2006). A comparison of the esterification of
acetic acid with methanol using heterogeneous versus homogeneous acid
catalysis. Journal of Catalysis 242: 278-286.
Mattson, F.H. and Volpenheim, R.A. (1972): Relative rates of
hydrolysis by rat pancreatic lipase of esters of C2-C18 fatty acids with
C1-C18 primary n-alcohols,Journal of Lipid Research, 10, 1969
Radzi, S.M. et al.(2005). High performance enzymatic synthesis of
oleyl oleate using immobilised lipase from Candida antartica. Electronic
Journal of Biotechnology 8: 292-298.
Tocher, D.R. (2003):Metabolism and function of lipids and fatty
acids in teleost fish,Reviews of Fisheries Science, 11 (2), 197
Zhao, Z. (2000). Synthesis of butyl propionate using novel
aluminophosphate molecular sieve as catalyst. Journal of Molecular
Catalysis 154(1-2): 131-135.
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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