Methyleugenol

178.23

178.23

202-223-0

29T9VA6R7M

209528|8900

2810

DTXSID5025607

C44401

Crystals from hexane|Colorless to pale yellow liquid

29093090

18.5

3.03 (est)

Methyleugenol is a clear colorless to pale yellow liquid with a spicy earthy odor. Bitter burning taste. (NTP, 1992)

1.0396 g/cm³ @ Temp: 20 °C

-4 °C

254.7 °C @ Press: 760 Torr

>230 °F

1.500

H2O: insoluble

2-8°C

0.02 mmHg

>1

Oral-rat LD50: 1179mg/kg; Abdominal cavity-mouse LD50: 540  mg/kg

Flammable; burning produces irritating fumes

Mild-spicy, slightly herbal odor

BITTER, BURNING TASTE

Henry's Law constant = 5.6X10-6 atm-cu m/mol at 25 °C (est)

138.94 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]|160.36 Ų [M+Na]+ [CCS Type: DT, Method: stepped-field]|133.68 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|133.2 Ų [M-H]-

Forms azeotropic mixtures with ethylene glycol (31.5%), eugenol (55%), benzoic acid (11%) & others.|Hydroxyl radical reaction rate constant = 7.5X10-11 cu cm/molec-sec at 25 °C (est)

Insoluble in water.

Ethers

METHYLEUGENOL is incompatible with strong oxidizers (NTP, 1992). May react exothermically with reducing agents to release hydrogen gas.

NONH for all modes of transport

1

22-36/37/38-40

26-36/37/39

CY2450000

Xn

Treasury is ventilated, low temperature and dry; stored separately from food materials

Stable. Combustible. Incompatible with strong oxidizing agents.

P280-P301 + P312 + P330-P305 + P351 + P338

H302-H315-H319-H335-H351-H411

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.

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]

This chemical is combustible. (NTP, 1992)

|Warning|H302 (99.94%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P272, P280, P281, P301+P312, P302+P352, P308+P313, P321, P330, P333+P313, P363, P405, and P501|Aggregated GHS information provided by 1708 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, and P501|P201, P202, P260, P261, P264, P270, P271, P273, P281, P301+P312, P304+P340, P305+P351+P338, P308+P313, P312, P314, P330, P337+P313, P403+P233, P405, and P501|P201, P202, P260, P264, P270, P281, P301+P312, P305+P351+P338, P308+P313, P314, P330, P332+P313, P337+P313, P405, and P501

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

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. STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store it under ambient temperatures. (NTP, 1992)

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. RECOMMENDED GLOVE MATERIALS: If this chemical makes direct contact with your gloves, or if a tear, puncture or hole develops, replace them at once. Glove Type Model Number Thickness Bkthru Time Viton North F-091 0.41 mm 480 min Neoprene Edmont 29-870 0.51 mm 135 min Latex Ansell 5.109 0.18 mm 15 min (NTP, 1992)

Use alcohol foam

| 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

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).

moderately toxic

LD50 Rabbit dermal >2025 mg/kg|LD50 Rat oral 1179 mg/kg|LD50 Mouse ip 540 mg/kg|LD50 Mouse iv 112 mg/kg|LD50 Mouse intraperitoneal > 640 mg/kg /table/

/FIELD STUDIES/ Field trapping of fruit flies by using methyl eugenol over 5 wk period was conducted in orchard in Gombak, Selangor. Traps with slit holes caught greatest number of flies. Over 85% of flies caught were male, Dacus dorsalis.

2-YEAR STUDY IN RATS: Groups of 50 male and 50 female F344/N rats received methyleugenol in 0.5% methylcellulose by gavage at doses of 37, 75 or 150 mg/kg, 5 days/week for 105 week; groups of 60 male and 60 female 344/N rats recieved 0.5% methylcellulose vehicle only. Stop-exposure groups of 60 male and 60 female F344/N rats received 300 mg/kg in 0.5% methylcellulose by gavage for 52 week followed by just the 0.5% methylcellulose vehicle for the remaining 53 week of the study. ... 2-YEAR STUDY IN MICE: Groups of 50 male and 50 female B6C3F1 mice received methyleugenol in 0.5% methylcellulose by gavage at doses of 0, 37, 75 or 150 mg/kg for 105 week. CONCLUSIONS: Under the conditions of these 2 yr gavage studies, there was clear evidence of carcinogenic activity of methyleugenol in male and female F344/N rats based on the increase incidences of liver neoplasms and neuroendocrine tumors of the glandular stomach in male and female rats and the increase incidences of kidney neoplams, malignant mesothelioma, mammary gland fibroadenoma, subcutaneous fibroma and fibroma or fibrosarcoma (combined) in male rats. A marginal increase in the incidence of squamous cell neoplasms of the forestomach may have been related to methyleugenol admin in female rats. There was clear evidence of carcinogenic activity of methyleugenol in male and female B6C3F1 mice based on the increase incidences of liver neoplasms. Neuroendocrine tumors of the glandular stomach in male mice were also considered related to methyleugenol admin.

...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's production and use as a flavoring agent(1) and in perfumery(2) may result in its release to the environment through various waste streams. Its use as an insect attractant(2), is expected to result in its direct release to the environment(SRC).

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).

The rate constant for the vapor-phase reaction of methyleugenol with photochemically-produced hydroxyl radicals has been estimated as 7.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of methyleugenol with ozone has been estimated as 1.2X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1 day at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). Methyleugenol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm).|Methyleugenol dissipated rapidly from both soil and water: at 32 °C 98% of the material was lost within 96 hours, and 77 and 81% were lost from water and soil, respectively, after 96 hours at 22 °C(1). Methyleugenol had a half-life of 6 hours in soil and water at 32 °C, and a half-life of 16 and 34 hours in soil and water, respectively, at 22 °C(1).

An estimated BCF value of 18 was calculated for methyleugenol(SRC), using a water solubility of 500 mg/L(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).

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).

The Henry's Law constant for methyleugenol is estimated as 5.6X10-6 atm-cu m/mole(SRC) derived from its extrapolated vapor pressure, 0.012 mm Hg(1), and water solubility, 500 mg/L(2). This Henry's Law constant indicates that methyleugenol is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 9 days (SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 69 days(SRC). Methyleugenol's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Methyleugenol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).|Methyleugenol dissipates rapidly from both soil and water(1). At 32 °C, 98% of methyleugenol was lost within 96 hours; 77 and 81% were lost from water and soil, respectively, after 96 hours at 22 °C(1). These values correspond to a half-life of 6 hours in soil and water at 32 °C, and half-lives of 16 and 34 hours in soil and water, respectively, at 22 °C(1).

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

NIOSH (NOES Survey 1981-1983) has statistically estimated that 2,824 workers (877 of these are female) are potentially exposed to methyleugenol in the USA(1). Occupational exposure to methyleugenol may occur through dermal contact with this compound at workplaces where methyleugenol is produced or used. Monitoring data indicate that the general population may be exposed to methyleugenol via ingestion of food and inhalation and dermal contact with this compound and consumer products containing methyleugenol. (SRC)

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).

Anesthetics|Medication (vet): methyleugenol suspended in tween-80 or cremophorel, at 200 to 275 mg/kg ip, is a safe anesthetic agent in rats and mice submitted to surgical procedures in brain, without some of inconvenience of sodium pentobarbital.

Agents that are 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. (See all compounds classified as Anesthetics.)|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. (See all compounds classified as Carcinogens.)|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. (See all compounds classified as Mutagens.)

... 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).

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.

...The /human/ half-life of elimination was about 90 min.

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. ACUTE/CHRONIC HAZARDS: This compound may be irritating to the skin and eyes. When heated to decomposition it emits acrid smoke, irritating fumes and toxic fumes of carbon monoxide and carbon dioxide. (NTP, 1992)|Carcinogens

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Maintain and open airway and assist ventilations if necessary. Treat seizures and coma if they occur There are no specific antidote for /these essential oils/. Administer activated charcoal, if available. Do not induce vomiting because of the risk of abrupt onset of seizures. Gastric emptying is not necessary for small ingestions if activated charcoal can be given promptly. /Camphor and Other Essential Oils/|The volumes of distribution of camphor and other essential oils is extremely large, and it is unlikely that any enhanced removal procedure will remove significant amounts of /these essential oils/. Poorly substantiated case reports have recommended hemoperfusion. /Camphor and Other Essential Oils/

/HUMAN EXPOSURE STUDIES/ Maximization test was carried out on 25 volunteers. Methyleugenol tested at concentration of 8% in petrolatum produced no reactions /after 48 hr closed-patch test/.

1-allyl-3,4-dimethoxybenzene

SMALL, ABSORBENT FIBER BLOCKS CONTAINING COMBINATION OF LURE & NALED...|Grades: Technical, FCC|Vizubon-D (+naled)

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.

Characteristic aroma of China rose was studied. Aroma components of rose concrete were separated by column chromatography of steam distillate & individual components were identified by mass spectrometry combined with gas chromatography. Methyleugenol was one of major aroma components.|Methyleugenol was one of components determined in essential oils by negative ion chemical ionization mass spectrometry.|Analysis by glc.

Flavoring Agents -> JECFA Flavorings Index|Health Hazards -> Carcinogens|Cosmetics -> Masking

Flavoring Agents