Methyleugenol

Other Classes -> Ethers, Other

Carcinogens

Cosmetics ingredient -> Flavor; Fragrance; Other (Specify); Solvent

Masking

Fragrance substance (Methyl eugenol) -> IFRA amendment 51

Fragrance Ingredient (Eugenyl methyl ether) -> IFRA transparency List

Fragrance

Mild-spicy, slightly herbal odor

Clove, carnation odor

1.0396 at 68 °F (NTP, 1992) - Denser than water; will sink

1.032-1.036 at 25 °C

1.032-1.036

Crystals from hexane

Colorless to pale yellow liquid

less than 1 mg/mL at 66 °F (NTP, 1992)

Soluble in most organic solvents

Soluble in ethanol, ethyl ether

Soluble in fixed oils; insoluble in glycerin and propylene glycol

In water, 500 mg/L at 25 °C

0.5 mg/mL at 25 °C

210 °F (NTP, 1992)

99 °C

99 °C (210 °F) (closed cup)

This chemical does not meet GHS hazard criteria for 6.1% (110 of 1814) of reports.

Warning

H302 (93.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P270, P272, P280, P301+P317, P302+P352, P318, P321, P330, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1814 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Chemical: Benzene, 1,2-dimethoxy-4-(2-propenyl)-

Hazard Traits - Carcinogenicity

Regulation (EC) No 1831/2003 (amended)

Benzene, 1,2-dimethoxy-4-(2-propen-1-yl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1,2-dimethoxy-4-(2-propen-1-yl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 10-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/23881

Methyl eugenol: Does not have an individual approval but may be used under an appropriate group standard

SYMPTOMS: Symptoms of exposure to this compound include nausea, vomiting, diarrhea, circulatory collapse, dizziness, rapid and shallow breathing, unconsciousness, convulsions, abdominal burning, dysuria, hematuria, tachycardia, bronchial irritation, anuria, pulmonary edema, bronchial pneumonia and renal damage.

Methyleugenol is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Methyleugenol (93-15-2) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s109meth.pdf]

Toxicology & Carcinogenesis Studies of Methyleugenol in F344/N Rats and B6C3F1 Mice p.8-10 Technical Report Series No. 491 (2000) NIH Publication No. 00-3950 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709

USEPA/Office of Pesticide Programs; Report of the Food Quality Protection Act (FQPA) Tolerance Reassessment Progress and Risk Management Decision (TRED) for Methyl Eugenol. December 2004. The Federal Food, Drug and Cosmetic Act (FFDCA)... requires EPA to reassess all the tolerances for registered chemicals in effect on or before the enactment of the FQPA on August 3, 1996. ...The Agency has evaluated the potential risks associated with methyl eugenol and has determined, that there is a reasonable certainty that no harm to any population subgroup will result from dietary and water exposure to methyl eugenol from uses specified in the existing exemption for the requirement for tolerance for methyl eugenol under 40 CFR 180.1067. Therefore, no mitigation measures are needed, and the exemption from the requirement of tolerances established in 40 CFR 180.1067 for residues of methyl eugenol on raw agricultural commodities are now considered reassessed under section 408(q) of the FFDCA.[Available from, as of July 27, 2005: http://www.epa.gov/pesticides/reregistration/status.htm]

Methyl eugenol and malathion combination; exemption from the requirement of a tolerance. The insect attractant methyl eugenol and the insecticide malathion are exempt from the requirement of tolerances on all raw agricultural commodities when used in combination in Oriental fruit fly eradication programs under the authority of the U.S. Department of Agriculture, in accordance with the following directions and specifications: (a) The combination shall be at the ratio of three parts methyl eugenol to one part technical malathion (3:1). (b) This combination is to be impregnated on a carrier (cigarette filter tips (cellulose acetate); cotton strings; fiberboard squares) or mixed with a jel cleared under 40 CFR 180.920 or 180.950. (c) The maximum actual dosage per application per acre shall be 28.35 grams (one ounce avoirdupois) methyl eugenol and 9.45 grams (one-third (0.33) ounce avoirdupois) technical malathion.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Methyl eugenol and malathion combination; exemption from the requirement of a tolerance. The insect attractant methyl eugenol and the insecticide malathion are exempt from the requirement of tolerances on all raw agricultural commodities when used in combination in Oriental fruit fly eradication programs under the authority of the U.S. Department of Agriculture, in accordance with the following directions and specifications: (a) The combination shall be at the ratio of three parts methyl eugenol to one part technical malathion (3:1). (b) This combination is to be impregnated on a carrier (cigarette filter tips (cellulose acetate); cotton strings; fiberboard squares) or mixed with a jel cleared under 40 CFR 180.920 or 180.950. (c) The maximum actual dosage per application per acre shall be 28.35 grams (one ounce avoirdupois) methyl eugenol and 9.45 grams (one-third (0.33) ounce avoirdupois) technical malathion.

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter.

Methyleugenol was detected in 98% of serum samples taken from 206 human volunteers who participated in the Third National Health and Nutrition Examination Survey conducted between 1988 and 1994. Mean and median levels of methyleugenol were 24 and 16 pg methyleugenol per gram of serum (whole-weight basis), respectively(1). In nine fasted volunteers, ingestion of cookies containing approximately 216 micrograms methyleugenol (3.7 ug/kg body weight) resulted in peak serum concentrations of 25-100 pg/g with a mean of 16 pg/g(2).

LC50 Lepomis macrochirus (Bluegill) 8.5 mg/L/24 hr; static /formulated product/

LC50 Lepomis macrochirus (Bluegill) 8.1 mg/L/48 hr (95% confidence interval: 7.4-9.0 mg/L); static /formulated product/

LC50 Lepomis macrochirus (Bluegill) 8.1 mg/L/96 hr (95% confidence interval: 7.4-9.0 mg/L); static /formulated product/

LC50 Oncorhynchus mykiss (Rainbow trout, donaldson trout) >5.6-<10 mg/L/24 hr; static /formulated product/

For more Ecotoxicity Values (Complete) data for METHYLEUGENOL (6 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 140(SRC), determined from a water solubility of 500 mg/L(2) and a regression-derived equation(3), indicates that methyleugenol is expected to have high mobility in soil(SRC). Volatilization of methyleugenol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.6X10-6 atm-cu m/mole(SRC), derived from its extrapolated vapor pressure, 0.012 mm Hg(4), and water solubility(2). Dissipation half-lives of 6 and 16 hours in soil and water at 32 and 22 °C, respectively, have been measured(5). Methyleugenol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). A theoretical BOD of 86-91% in 4 weeks using an activated sludge inoculum and the Japanese MITI test(6) indicates that biodegradation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 140(SRC), determined from a water solubility of 500 mg/L(2) and a regression-derived equation(3), indicates that methyleugenol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 5.6X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.012 mm Hg(4), and water solubility(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 9 and 69 days, respectively(SRC). Dissipation half-lives of 6 and 34 hours in water at 32 and 22 °C, respectively, have been measured(5). According to a classification scheme(6), an estimated BCF of 18(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A theoretical BOD of 86-91% in 4 weeks using an activated sludge inoculum and the Japanese MITI test(7) indicates that biodegradation may be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyleugenol, which has an extrapolated vapor pressure of 0.012 mm Hg at 25 °C(2) is expected to exist almost entirely as a vapor in the ambient atmosphere. Vapor-phase methyleugenol is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 5 hours(SRC), calculated from its rate constant of 7.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

...IN ESSENTIAL OILS OF MYRTACEAE & LAURACEAE. ...IDENTIFIED ORIGINALLY IN ESSENTIAL OIL FROM ROOTS OF ASARUM EUROPAEUM L & ASARUM CANADENSE L, SUBSEQUENTLY...IDENTIFIED AS MAIN CONSTITUENT OF OIL FROM WOOD OF DACRYDIUM FRANKLINII (97.5%), IN MELALEUCA BRACTEATA (LEAVES 90-95%), IN CINNAMOMUM OLIVERI (LEAVES 90-95%) & AS MINOR CONSTITUENT IN OILS OF: BETEL, CITRONELLA, JAPANESE CALAMUS, PIMENTA, HYACINTH, ROSE, BASIL, BAY CAJEPUT & OTHERS.

Methyleugenol was identified as a volatile flavor compound in the juice of Kogyoku apples(1).

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=93-15-2]

Methyleugenol was detected at a concentration of 5 ppb in wastewater from a New Jersey publicly owned treatment works facility located in an industrial site (industrial contribution to the influent is 18%)(1). Methyleugenol was detected in paper mill wastewater at two different sample points at 0.002 and 0.001 mg/L(2).

The Koc of methyleugenol is estimated as 140(SRC), using a water solubility of 500 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that methyleugenol is expected to have high mobility in soil. However, the compound was immobile in silty loam, Lufkin fine sandy loam, Houston clay, and Brazos river bottom sand using soil thin layer chromatography(4).

...IN ESSENTIAL OILS OF MYRTACEAE & LAURACEAE. ...IDENTIFIED ORIGINALLY IN ESSENTIAL OIL FROM ROOTS OF ASARUM EUROPAEUM L & ASARUM CANADENSE L, SUBSEQUENTLY...IDENTIFIED AS MAIN CONSTITUENT OF OIL FROM WOOD OF DACRYDIUM FRANKLINII (97.5%), IN MELALEUCA BRACTEATA (LEAVES 90-95%), IN CINNAMOMUM OLIVERI (LEAVES 90-95%) & AS MINOR CONSTITUENT IN OILS OF: BETEL, CITRONELLA, JAPANESE CALAMUS, PIMENTA, HYACINTH, ROSE, BASIL, BAY CAJEPUT & OTHERS.

Methyleugenol was identified as a volatile flavor compound in the juice of Kogyoku apples(1). Methyleugenol occurs as a component of rose oil and pimento oil(2).

Methyleugenol is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

Methyl eugenol and malathion combination; exemption from the requirement of a tolerance. The insect attractant methyl eugenol and the insecticide malathion are exempt from the requirement of tolerances on all raw agricultural commodities when used in combination in Oriental fruit fly eradication programs under the authority of the U.S. Department of Agriculture, in accordance with the following directions and specifications: (a) The combination shall be at the ratio of three parts methyl eugenol to one part technical malathion (3:1). (b) This combination is to be impregnated on a carrier (cigarette filter tips (cellulose acetate); cotton strings; fiberboard squares) or mixed with a jel cleared under 40 CFR 180.920 or 180.950. (c) The maximum actual dosage per application per acre shall be 28.35 grams (one ounce avoirdupois) methyl eugenol and 9.45 grams (one-third (0.33) ounce avoirdupois) technical malathion.

In rat, eugenol methyl ether underwent oxidation of allylic side chain to form 3 metabolites, 2 of which were excreted as glycine conjugates. Other metabolic reactions were hydroxylation of benzene ring, o-demethylation, and 2 oxidation reactions; 63-95% of initial dose was accounted for. Most of metabolites were found in bile.

Methyleugenol has known human metabolites that include 1-hydroxylate methyleugenol.

Agents capable of inducing a total or partial loss of sensation, especially tactile sensation and pain. They may act to induce general ANESTHESIA, in which an unconscious state is achieved, or may act locally to induce numbness or lack of sensation at a targeted site.

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.

... A study was conducted with nine healthy adult male and female human volunteers. ... The mean fasting level of methyleugenol in serum was 16.2 +/- 4.0 pg/g wet weight. Peak blood levels were found at 15 min (mean +/- SD, 53.9 +/- 7.3 pg/g wet weight), followed by a rapid decline; the half-life of elimination was about 90 min. The peak levels were within the range of methyleugenol blood levels in the U.S. population, as measured concurrently in a subset of nonfasting participants in the Third National Health and Nutrition Examination Survey (NHANES III).

Used as a veterinary anesthetic, insect attractant, and flavoring agent; [HSDB] Used as a fragrance ingredient in perfumes, toiletries, and detergents; [Merck Index]

For methyl eugenol (USEPA/OPP Pesticide Code: 203900) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Insect attractant; flavoring agent

Oriental fruit fly attractant.

MEDICATION (VET)

Methyleugenol is used as a flavorant in commercial products at concentrations of 5 to 52 ppm. Methyleugenol is used in fragrances at a concentration of 0.002 to 0.3%.

Methyl eugenol

Methyl eugenol; Eugenol methyl ether; Eugenyl methyl ether; Methyl eugenol ether; Allylveratrole; 4-Allylveratrole; Veratrole methyl ether; 4-Allyl-1,2-dimethoxybenzene; Benzene, 1,2-dimethoxy-4-(2-propenyl)-; 1,2-Dimethoxy-4-allylbenzene; 1,2-dimethoxy-4-(2-propenyl)-benzene; 3,4-Dimethoxyallylbenzene

IFRA_STD_100.pdf

51

IFRA 51st Amendment - Guidance for the use of IFRA Standards

Restriction: This material should be used only in the limited quantity as stated in the Standard

SMALL, ABSORBENT FIBER BLOCKS CONTAINING COMBINATION OF LURE & NALED...

Grades: Technical, FCC

Vizubon-D (+naled)

Cosmetics product ingredient: Methyleugenol (Methyl eugenol)

Information on 6 consumer products that contain Methyleugenol in the following categories is provided:

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Cosmetics -> Masking

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

Benzene, 1,2-dimethoxy-4-(2-propen-1-yl)-: ACTIVE

Baked goods 39.86 ppm; frozen dairy 17.35 ppm; condiment, relish 7.15 ppm; soft candy 23.92 ppm; gelatin, pudding 17.34 ppm; non-alcoholic beverages 11.55 ppm; hard candy 0.60 ppm; chewing gum 44.61 ppm

Concentration in final product (%): usual/maximum; soap 0.02/0.2, detergent 0.002/0.02, creams, lotions 0.01/0.05, perfume 0.3/0.8.

0.00042 [Products applied to the lips]

0.0015 [Products applied to the axillae]

0.00042 [Products applied to the face/body using fingertips]

0.011 [Products related to fine fragrances]

0.0015 [Products applied to the body using the hands (palms), primarily leave-on (Body lotion)]

0.00021 [Products applied to the face using the hands (palms), primarily leave-on (Face moisturizer)]