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Home > Encyclopedia > L-MENTHYL ACETATE

L-MENTHYL ACETATE

L-MENTHYL ACETATE structure

L-MENTHYL ACETATE 

structure
  • CAS No:

    16409-45-3

  • Formula:

    C12H22O2

  • Chemical Name:

    L-MENTHYL ACETATE

  • Synonyms:

    2-Isopropyl-5-methylcyclohexyl acetate;MENTHYL ACETATE, L-;(R)-(-)-MENTHYL ACETATE;(-)-ACETOXY-P-MENTHANE;Acetic acid 2-isopropyl-5-methylcyclohexyl ester;Acetic acid 5-methyl-2-(1-methylethyl)cyclohexyl ester;Acetic acid p-menthane-3-yl ester;DL-MENTHYL ACETATE 97+% FCC

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

Liquid|colourless to pale yellowish liquid with a mild, minty odour


Colorless liquid; menthol-like odor.Slightly soluble in water; miscible with alcohol and ether. Combustible.


l-Menthyl acetate has a fresh odor similar to mint and rose (on dilution). It has a characteristic, fresh, pungent flavor, different from menthol (being much milder). It has a cool mouthfeel with only a trace of mint flavor.


ChEBI: (+/-)-Menthyl acetate is a p-menthane monoterpenoid.


Mildly toxic by ingestion. A skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

L-MENTHYL ACETATE Basic Attributes

198.3

198.30

240-459-6

122112|7350

DTXSID9041817|DTXSID7051472

Characteristics

0.92 g/mL at 25 °C(lit.)

<25 °C

229-230 °C(lit.)

n20/D1.447(lit.)

soluble in alcohol, propylene glycol, most fixed oils; slightly soluble in water, glycerol|1 ml in 6 ml 70% alcohol; 1 ml in 1 ml 80% alcohol (in ethanol)

0.10 mmHg

rabbit,LD50,skin,> 5gm/kg (5000mg/kg),Food and Cosmetics Toxicology. Vol. 14, Pg. 479, 1976.

at 100.00 %. tea cooling minty fruity berry

EARTHY, WEEDY, FRUITY, BERRY-LIKE TASTE

1.2×10-2mol/(m3Pa) at 25℃, HSDB (2015)

FRESH ODOR SIMILAR TO MINT & ROSE (ON DILUTION); CHARACTERISTIC, FRESH PUNGENT FLAVOR, MILDER THAN MENTHOL; COOL MOUTHFEEL WITH ONLY A TRACE OF MINT FLAVOR; SPECIFIC GRAVITY: 0.9220-0.9310 AT 25 °C; 0.9264 AT 20 °C /L-ISOMER/|SYNTHETIC PRODUCT IS OPTICALLY LEVO ROTATORY; THE COMMERCIAL PRODUCT IS OPTICALLY INACTIVE; SPECIFIC OPTICAL ROTATION: +2 TO -2 DEG (COMMERCIAL PRODUCT), -72 DEG 47 SEC TO -73 DEG 16 SEC (L-ISOMER)|Colorless liquid, characteristic odor; density = 0.919 at 20 °C/4 °C; boiling point = 227 °C; Index of refraction = 1.4468 at 20 °C/D; Specific optical rotation = -79.42 deg at 20 °C/D; slightly soluble in water; miscible with alcohol, ether /L-Menthyl acetate/.

Safety Information

3

AI5900000

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Menthyl acetate is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient. Isobutyl acetate synthetic flavoring substances & adjuvants may be safely used in food in accordance with the following conditions ... They consist of one or more of the following /substances including isobutyl acetate/ used alone or in combination with flavoring substances generally recognized as safe in food, or regulated by an appropriate section in this part.

|H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|P273, P391, and P501|Aggregated GHS information provided by 1549 companies from 5 notifications to the ECHA C&L Inventory.|H411 (99.81%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|Aggregated GHS information provided by 538 companies from 6 notifications to the ECHA C&L Inventory.|Aggregated GHS information provided by 25 companies from 1 notifications to the ECHA C&L Inventory.|Aggregated GHS information provided by 1648 companies from 2 notifications to the ECHA C&L Inventory.|Warning|H228 (100%): Flammable solid [Danger Flammable solids]|P210, P240, P241, P273, P280, P370+P378, P391, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Aggregated GHS information provided by 315 companies from 1 notifications to the ECHA C&L Inventory.

Toxicity

Menthyl acetate is present in peppermint oil(1).

Menthyl acetate's production and use in perfumery(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5800(SRC), determined from an estimated log Kow of 4.39(2,SRC) and a regression-derived equation(3), indicates that menthyl acetate is expected to be immobile in soil(SRC). Volatilization of menthyl acetate from moist soil surfaces is expected to occur(SRC) given an estimated Henry's Law constant of 8.3X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, volatilization from moist soil surfaces is expected to be attenuated by adsorption to organic matter(SRC). In general, acetates are expected to be readily biodegradable(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5800(SRC), determined from an estimated log Kow of 4.39(2,SRC) and a regression-derived equation(3), indicates that menthyl acetate is expected to adsorb to suspended solids and sediment in water(SRC). Menthyl acetate is expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 8.3X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated volatilization half-lives for a model river and model lake are 5.6 hours and 6.0 days, respectively(3,SRC). However, adsorption to suspended solids and sediment in the water column is expected to attenuate this process(SRC). The volatilization half-life from a model pond 2 m deep is estimated to be about 2.7 days ignoring adsorption(5); when considering maximum adsorption, the volatilization half-life increases to 94 days(5). According to a classification scheme(6), an estimated BCF of 1300(3,SRC), from an estimated log Kow(2,SRC), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). In general, acetates are expected to be readily biodegradable(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), menthyl acetate, which has a vapor pressure of 0.10 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase menthyl acetate 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 21 hours(3,SRC).

The rate constant for the vapor-phase reaction of menthyl acetate with photochemically-produced hydroxyl radicals has been estimated as 1.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 21 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). A base-catalyzed second-order hydrolysis rate constant of 3.0X10-2 L/mol-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 7.3 years and 270 days at pH values of 7 and 8, respectively(2,SRC).

An estimated BCF of 1300 was calculated for menthyl acetate(SRC), using an estimated log Kow of 4.39(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC).

The Koc of menthyl acetate is estimated as approximately 5800(SRC), using an estimated log Kow of 4.39(1,SRC) and a regression-derived equation(2,SRC). According to a classification scheme(3), this estimated Koc value suggests that menthyl acetate is expected to be immobile in soil(SRC).

The Henry's Law constant for menthyl acetate is estimated as 8.3X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that menthyl acetate is expected to volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the estimated volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is approximately 5.6 hours(2,SRC). The estimated volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is approximately 6.0 days(2,SRC). The volatilization half-life from a model pond 2 m deep is estimated to be about 2.7 days ignoring adsorption(3); when considering maximum adsorption, the volatilization half-life increases to 94 days(3). Menthyl acetate's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces may occur(SRC).

DRINKING WATER: Menthyl acetate was qualitatively detected in drinking water in Seattle, WA in 1976(1).

Occupational exposure to menthyl acetate may occur through inhalation and dermal contact with this compound at workplaces where menthyl acetate is produced or used. The general population may be exposed to menthyl acetate via inhalation and dermal contact with consumer products, such as perfumes, containing menthyl acetate, and via ingestion of food. (SRC)

Drug Information

AS AN ESTER IT IS PRESUMABLY HYDROLYZED IN THE ALIMENTARY TRACT TO MENTHOL AND ACETIC ACID.

L-MENTHYL ACETATE Use and Manufacturing

Methods of Manufacturing

BY REACTING ACETIC ANHYDRIDE WITH MENTHOL IN THE PRESENCE OF ANHYDROUS SODIUM ACETATE. NATURAL OCCURRENCE: ...A NORMAL CONSTITUENT OF PEPPERMINT OIL IN VARYING AMOUNTS, DEPENDING ON THE SOURCE. /L-ISOMER/

Uses

Odor agents


Air care products


L-Menthyl Acetate is a component of essential oils extracted from natural sources.


Perfumery, flavoring.

Production

< 25,000 lb

GRADE: 95% MIN. /L-ISOMER/

fragrances|Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 1-acetate, (1R,2S,5R)-rel-: ACTIVE|FEMA NUMBER: 2668; REPORTED USES: NON-ALCOHOLIC BEVERAGES 5.5 PPM; ICE CREAM, ICES 4.0 PPM; CANDY 26 PPM; BAKED GOODS 24 PPM; CHEWING GUM 5.2 PPM. /L-ISOMER/

Food additives -> Flavoring Agents|Cosmetics -> Masking; Refreshing

Flavoring Agents

Drug Function and Efficacy

Enhances aroma complexity and modulates intensity of cooling sensation

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

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