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Methyleugenol (Ref: Ent 21040)
Last updated: 22/05/2024
(Also known as: methyl eugenol; Eugenol methyl ether; a-allylveratrole; 4-allylveratrole ; NSC 209528; O-methyleugenol)
GENERAL INFORMATION
Description
Chemical transformation product also used as an insect parapheromone used in traps to attract certain species such as the oriental fruit fly
Availability status
-
Introduction & key dates
-
Examples of veterinary uses
-
Examples of species treated
-
Approval status
VMR 2013/2033 approval status (GB/UK)
-
EU Regulatory approval status
-
Chemical structure
Isomerism
-
Chemical formula
C₁₁H₁₄O₂
Canonical SMILES
COC1=C(C=C(C=C1)CC=C)OC
Isomeric SMILES
-
International Chemical Identifier key (InChIKey)
ZYEMGPIYFIJGTP-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4,6-8H,1,5H2,2-3H3
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
Eugenol Parent
General status
Veterinary substance type
-
Metabolite Type
Soil
Substance groups
Plant-derived substance
Minimum active substance purity
>98%
Known relevant impurities
<1% Eugenol
Substance origin
Natural
Mode of action
Not applicable
Molecular targets
-
CAS RN
93-15-2
EC number
202-223-0
CIPAC number
-
US EPA chemical code
-
PubChem CID
-
Therapeutic Class
-
ATCvet Code
-
Controlled Drug?
-
Regulation 37/2010 MRL Classification
-
Molecular mass
178.23
PIN (Preferred Identification Name)
-
IUPAC name
1,2-dimethoxy-4-prop-2-en-1-ylbenzene
CAS name
1,2-dimethoxy-4-(2-propenyl)benzene
Other status information
Registered food additive; FEMA 2475; CoE 185
Relevant Environmental Water Quality Standards
-
Physical state
Colourless to pale yellow liquid
Can be a metabolite of:
Parent
Formation medium
Estimated maximum occurrence fraction
1107/2009 relevancy
eugenol Soil - -
Formulations
Property
Product
Manufacturer
Authorisation Route
Legal Class (GB/UK)
Example products (past and present) using this active
- - - -
Formulation and application details
-
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
500
D4 D = Agricultural Research Information System (ARIS) Database. Dataset is no longer available.
4 = Verified data
 Moderate
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
-2
Q4 Q = Miscellaneous data from online sources
4 = Verified data
 -
Boiling point (°C)
146
Q4 Q = Miscellaneous data from online sources
4 = Verified data
 -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
2.82 X 1003 Calculated -
Log P
3.45
Q4 Q = Miscellaneous data from online sources
4 = Verified data
 High
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.0396
Q4 Q = Miscellaneous data from online sources
4 = Verified data
 -
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)
- - -
Refractive Index
- - -
Environmental release
-
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
- - -
DT₅₀ (lab at 20 °C)
0.25
Q4 Q = Miscellaneous data from online sources
4 = Verified data
 Non-persistent
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
0.25
Q4 Q = Miscellaneous data from online sources
4 = Verified data
 Non-persistent
DT₉₀ (field)
- - -
Note
Shown to rapidly dissipate in soil, 98% lost within 96hrs
Manure DT₅₀ (days)
- - -
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)
- - -
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
- - -
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)
- - -
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)
242.25
D4 D = Agricultural Research Information System (ARIS) Database. Dataset is no longer available.
4 = Verified data
Eisenia foetida		 Low
Soil micro-organisms
- - -
Collembola
Acute LC₅₀ (mg kg⁻¹)
- - -
Chronic NOEC (mg kg⁻¹)
- - -
Non-target plants
- - -
- - -
Honeybees (Apis spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
> 100
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 Low
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
- - -
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)
8.5
D4 D = Agricultural Research Information System (ARIS) Database. Dataset is no longer available.
4 = Verified data
Lepomis macrochirus		 Moderate
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
38
D4 D = Agricultural Research Information System (ARIS) Database. Dataset is no longer available.
4 = Verified data
Daphnia magna		 Moderate
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
1.1
D4 D = Agricultural Research Information System (ARIS) Database. Dataset is no longer available.
4 = Verified data
Daphnia magna		 Moderate
Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
- - -
Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)
- - -
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)
- - -
Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
22.0
D4 D = Agricultural Research Information System (ARIS) Database. Dataset is no longer available.
4 = Verified data
Pseudokirchneriella subcapitata		 Low
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
4.6
D4 D = Agricultural Research Information System (ARIS) Database. Dataset is no longer available.
4 = Verified data
Pseudokirchneriella subcapitata		 Low
Mesocosm study data
NOEAEC mg l⁻¹
- - -
NOEAEC mg l⁻¹
- - -
Marine bivalves
- - -
HUMAN HEALTH AND PROTECTION
General
Property
Value
Source; quality score; and other information
Interpretation
Threshold of Toxicological Concern (Cramer Class)
High (class III) - -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
- - -
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
- - -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
- - -
Other Mammal toxicity endpoints
- - -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
- - -
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
- - -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)
- - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)
- - -
Dermal penetration studies (%)
- - -
Dangerous Substances Directive 76/464
- - -
Exposure Routes
Public
-
Occupational
-
Mammalian dose elimination route and rate
- - -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
?Possibly, status not identified
A0 A = Chromosome aberration (EFSA database)
0 = No data
;
B0 B = DNA damage/repair (EFSA database)
0 = No data
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E3 E = Unspecified genotoxicity type (miscellaneous data source)
3 = Negative
XNo, known not to cause a problem
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
?Possibly, status not identified
XNo, known not to cause a problem
 No data found
Respiratory tract irritant Skin irritant Skin sensitiser
No data found
?Possibly, status not identified
 No data found
Eye irritant Phototoxicant  
?Possibly, status not identified
 No data found  
General human health issues
Possible liver toxicant
IARC Group 2A - anticipated to be a human carcinogen; US NTP - listed as carcinogen; OSHA - Anticipated human carcinogen
Handling issues
Property
Value and interpretation
General
No information available
CLP classification 2013
-
WHO Classification
Not listed (Not listed)
UN Number
-
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
methyleugenol
French
-
German
-
Danish
-
Italian
-
Spanish
-
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-
Record last updated: 22/05/2024
Contact: aeru@herts.ac.uk
Please cite as: 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