Methyleugenol (Ref: Ent 21040)

Methyleugenol (Ref: Ent 21040)	Last updated: 20/10/2025
(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

Examples of veterinary uses

Examples of species treated

Approval status

VMR 2013/2033 approval status (GB/UK)

EU Regulatory approval status

Chemical structure

Isomerism

Methyleugenol primarily exhibits geometrical (cis-trans) isomerism due to the presence of a double bond in its allyl side chain. This unsaturation allows for two spatial arrangements: the cis (Z) and trans (E) forms, which differ in the relative positioning of substituents around the double bond.

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

Global Governance status: Listed (✓) under

UK Poisons List Order 1972	Rotterdam Convention	Montreal Protocol
XNo The Poisons List Order 1972	XNo Rotterdam Convention	XNo Montreal Protocol
Stockholm Convention	OSPAR	EU Water Framework Directive
XNo Stockholm Convention	XNo OSPAR	XNo EU Water Framework Directive

Relevant Environmental Water Quality Standards

Forever chemical

Other status information

FLAVIS=02.091; CoE 185

Physical state

Colourless to pale yellow liquid

Can be a metabolite of:

Parent

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

eugenol

Soil

Commercial

Property

Value

Availability status

Introduction & key dates

Example manufacturers & suppliers of products using this active now or historically

Example products using this active

Formulation and application details

Commercial production

Methyleugenol is commercially produced through the chemical methylation of eugenol, a naturally occurring phenolic compound found in essential oils like clove, nutmeg, and basil. The process typically involves reacting eugenol with a methylating agent such as dimethyl sulphate or methyl iodide in the presence of a base, often under controlled temperature and pressure to ensure selectivity and yield. This transformation converts the hydroxyl group of eugenol into a methoxy group, resulting in methyleugenol.

Impact on climate of production and use

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C at pH 7 (mg l⁻¹)

500

Moderate

Solubility - In organic solvents at 20 °C (mg l⁻¹)

Melting point (°C)

-2

Boiling point (°C)

146

Degradation point (°C)

Flashpoint (°C)

Octanol-water partition coefficient at pH 7, 20 °C

2.82 X 10⁰³

Calculated

Log P

3.45

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.0396

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

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

0.25

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)

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

K_d (mL g⁻¹)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

K_foc (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)

> 1179

Rat

Moderate

Mammals - Short Term Oral NOAEL (mg kg⁻¹ bw d⁻¹)

Mammals - Long Term (Chronic) Oral NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

Birds - Short term dietary LC₅₀ (mg kg⁻¹ bw d⁻¹)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹ dw soil)

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹ dw soil)

242.25

Eisenia foetida

Low

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)

> 100

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

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)

Beneficial insects (Butterflies)

Contact

Notes

Oral

Notes

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

8.5

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)

Daphnia magna

Moderate

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

1.1

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 (free-floating, fonds growth, fresh) - 7 day (mg l⁻¹)

Aquatic plants (rooted, growth rate, fresh) - 14 day (mg l⁻¹)

Algae - Acute (growth rate, fresh; mg l⁻¹) (EC₅₀)

22.0

Raphidocelis subcapitata

Low

Algae - Chronic (growth rate, fresh; mg l⁻¹) (NOEC)

4.6

Raphidocelis subcapitata

Low

Mesocosm study data

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)

> 1179

Rat

Moderate

Mammals - Short Term Oral NOAEL (mg kg⁻¹ bw d⁻¹)

Mammals - Long Term (Chronic) Oral NOAEL (mg kg⁻¹ bw d⁻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 (hazard-based)

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver toxicant
IARC Group 2A - anticipated to be a human carcinogen; US NTP - listed as carcinogen; CLP data - suspected of causing cancer; OSHA - Anticipated human carcinogen

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

Health: H302, H351

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:	20/10/2025
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

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