(Also known as: etohexadiol; ethyl hexanediol; octylene glycol; ethyl hexyleneglycol)
SUMMARY
Hazard alerts
The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement. These hazard alerts do not take account of usage patterns or exposure, thus do not represent risk.
Environmental fate
Ecotoxicity
Human health
Human health High alert: Reproduction/development effects
Warning: Significant data are missing
GENERAL INFORMATION
Description
An obsolete insect repellent
GB regulatory status
GB COPR regulatory status
Not approved
Date COPR inclusion expires
Not applicable
GB LERAP status
No UK approval for use as a plant protection agent
EC Regulation 1107/2009 (repealing 91/414)
EC Regulation 1107/2009 status
Not approved
Dossier rapporteur/co-rapporteur
Not applicable
Date EC 1107/2009 inclusion expires
Not applicable
EU Candidate for substitution (CfS)
Not applicable
Listed in EU database
No
Approved for use (✓) under EC 1107/2009 in the following EU Member States
ATAustria
BEBelgium
BGBulgaria
CYCyprus
CZCzech Republic
DEGermany
DKDenmark
EEEstonia
ELGreece
ESSpain
FIFinland
FRFrance
HRCroatia
HUHungary
IEIreland
ITItaly
LTLithuania
LULuxembourg
LVLatvia
MTMalta
NLNetherlands
PLPoland
PTPortugal
RORomania
SESweden
SISlovenia
SKSlovakia
Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries
ISIceland
NONorway
Additional information
Also used in
-
Chemical structure
Isomerism
Ethohexadiol exhibits stereoisomerism due to the presence of two chiral centres at the 1 and 3 positions of the hexane backbone. This structural feature allows for the formation of four stereoisomers: (2R,3R), (2S,3S), (2R,3S), and (2S,3R). These include both enantiomers and diastereomers. For insect repellents, the (threo)-isomer of ethohexadiol, specifically (2R,3R)-2-ethylhexane-1,3-diol, is the form most commonly used. However, commercially available ethohexadiol is typically supplied as a mixture of isomers.
Insecticide; Veterinary substance; Other substance
Other bioactivity & uses
Solvent
Substance groups
Aliphatic alcohol
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Repellent
CAS RN
94-96-2
EC number
202-377-9
CIPAC number
-
US EPA chemical code
041001
PubChem CID
7211
Molecular mass
146.23
PIN (Preferred Identification Name)
(2E,3E)-2-ethylhexane-1,3-diol
IUPAC name
(2RS,3RS;2RS,3SR)-2-ethylhexane-1,3-diol
CAS name
2-ethyl-1,3-hexanediol
Forever chemical
-
Other status information
-
Relevant Environmental Water Quality Standards
-
Herbicide Resistance Class (HRAC MoA class)
Not applicable
Herbicide Resistance Class (WSSA MoA class)
Not applicable
Insecticide Resistance Class (IRAC MoA class)
Not applicable
Fungicide Resistance Class (FRAC MOA class)
Not applicable
Examples of recorded resistance
-
Physical state
Colourless, slightly viscous liquid
Commercial
Property
Value
Availability status
Considered obsolete but may be available in some countries; Banned in some countries
Introduction & key dates
Circa 1945, introduced; 1991, withdrawn
Example manufacturers & suppliers of products using this active now or historically
-
Example products using this active
Rutgers 612
Formulation and application details
Formulated for topical application
Commercial production
Ethohexadiol is typically synthesised through a multi-step organic process starting with 2-ethylhexanal or related precursors. The key step involves hydroxylation of the alkyl chain to introduce hydroxyl groups at the 1 and 3 positions. This is often achieved via controlled oxidation or reduction reactions, depending on the starting material. For example, selective reduction of 2-ethylhexane-1,3-dione or oxidation of 2-ethylhexane derivatives can yield the desired diol. The reaction is usually carried out under mild conditions using metal catalysts or organic reagents, followed by purification through distillation or recrystallisation to isolate the ethohexadiol isomers.
Impact on climate of production and use
Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used.
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
-
-
-
Solubility - In organic solvents at 20 °C (mg l⁻¹)
-
-
-
Melting point (°C)
-40
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source
-
Boiling point (°C)
243.0
R3 R = Peer reviewed scientific publications 3 = Unverified data of known source
-
Degradation point (°C)
-
-
-
Flashpoint (°C)
129.0
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source
-
Octanol-water partition coefficient at pH 7, 20 °C
P
-
-
-
Log P
-
-
-
Fat solubility of residues
Solubility
-
-
-
Data type
-
-
-
Density (g ml⁻¹)
0.942
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source
-
Dissociation constant pKa) at 25 °C
-
-
-
-
Vapour pressure at 20 °C (mPa)
-
-
-
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
-
-
-
Volatilisation as max % of applied dose lost
From plant surface
-
-
-
From soil surface
-
-
-
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
-
-
-
Surface tension (mN m⁻¹)
-
-
-
Degradation
Property
Value
Source; quality score; and other information
Interpretation
General biodegradability
-
Soil degradation (days) (aerobic)
DT₅₀ (typical)
-
-
-
DT₅₀ (lab at 20 °C)
-
-
-
DT₅₀ (field)
-
-
-
DT₉₀ (lab at 20 °C)
-
-
-
DT₉₀ (field)
-
-
-
DT₅₀ modelling endpoint
-
-
-
Note
-
Dissipation rate RL₅₀ (days) on plant matrix
Value
-
-
-
Note
-
Dissipation rate RL₅₀ (days) on and in plant matrix
Value
-
-
-
Note
-
Aqueous photolysis DT₅₀ (days) at pH 7
Value
-
-
-
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
-
-
-
Note
-
Water-sediment DT₅₀ (days)
-
-
-
Water phase only DT₅₀ (days)
-
-
-
Sediment phase only DT₅₀ (days)
-
-
-
Air degradation
As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.
Decay in stored produce DT₅₀
-
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd (mL g⁻¹)
-
-
-
Koc (mL g⁻¹)
-
Notes and range
-
Freundlich
Kf (mL g⁻¹)
-
-
-
Kfoc (mL g⁻¹)
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
-
-
-
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
Cannot be calculated
-
-
Note
-
Potential for particle bound transport index
-
-
-
Potential for loss via drain flow
-
-
-
Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk
-
-
-
Bio-concentration factor
BCF (l kg⁻¹)
-
-
-
CT₅₀ (days)
-
-
Known metabolites
None
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 1400
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source
Rat
Moderate
Mammals - Short term dietary NOEL
(mg kg⁻¹)
-
-
-
(ppm diet)
-
-
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
-
-
-
Birds - Acute LD₅₀ (mg kg⁻¹)
-
-
-
Birds - Short term dietary (LC₅₀/LD₅₀)
-
-
-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
-
-
-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
-
-
-
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
-
-
-
Soil micro-organisms
-
-
-
Collembola
Acute LC₅₀ (mg kg⁻¹)
-
-
-
Chronic NOEC (mg kg⁻¹)
-
-
-
Non-target plants
Vegetative vigour ER₅₀ (g ha⁻¹)
-
-
-
Seedling emergence ER₅₀ (g ha⁻¹)
-
-
-
Honeybees (Apis spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
-
-
-
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
-
-
-
Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
-
-
-
Chronic
-
-
-
Notes
-
Bumblebees (Bombus spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
-
-
-
-
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
-
-
-
-
Mason bees (Osmia spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
-
-
-
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
-
-
-
Other bee species (1)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
-
-
-
Mode of exposure
-
Other bee species (2)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
-
-
-
Mode of exposure
-
Beneficial insects (Ladybirds)
-
-
-
Beneficial insects (Lacewings)
-
-
-
Beneficial insects (Parasitic wasps)
-
-
-
Beneficial insects (Predatory mites)
-
-
-
Beneficial insects (Ground beetles)
-
-
-
Aquatic ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
-
-
-
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)
-
-
-
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242
Human health
Warning:
