D-Menthone

154.25

154.25

222-227-6

15F1B5K9A5

DTXSID2044478

Colorless, oily, mobile liq

2914299000

17.1

2.64770

colourless to pale yellowish liquid with a mint-like odour

0.881g/cm3

209-210 °C(lit.)

72 °C

n20/D 1.450

In water, 688 mg/l @ 25 deg C

2-8°C

Slight peppermint odor

Bitter

BP: 207 °C, 116-119 °C @ 41 mm Hg; MP: -6 °C; Density: 0.895 @ 20 °C/4 °C /L-form/|SPECIFIC OPTICAL ROTATION +24.85 DEG @ 18 °C/D; MAX ABSORPTION (ALC): 236 NM (LOG E= 1.40); 287 NM (LOG E= 1.38); BP: 204 °C @ 750 MM HG; DENSITY: 0.8963 @ 20 °C/20 °C; INDEX OF REFRACTION: 1.4503 @ 20 °C /D-FORM/|COLORLESS LIQUID /OPTICALLY ACTIVE FORM/|Index of refraction: 1.4505 @ 20 °C; 1.4490 @ 23 °C; Specific optical rotation: -24.8 deg @ 20 °C/D; -28.9 Deg @ 27 °C/D /L-form/

NONH for all modes of transport

3

23-24/25

P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P302+P352, P303+P361+P353, P321, P332+P313, P333+P313, P362, P363, P370+P378, P403+P235, P501

H226

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.

Menthone 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.

H412 (100%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|P273, and P501|Aggregated GHS information provided by 28 companies from 1 notifications to the ECHA C&L Inventory.| |Warning|H226 (74.75%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P302+P352, P303+P361+P353, P321, P332+P313, P333+P313, P362, P363, P370+P378, P403+P235, and P501|Aggregated GHS information provided by 1803 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Menthone was identified, not quantified, in the exudate of garden wastes(1).

LD50 Oral rat 500 mg/kg|LD50 Mouse sc 2180 mg/kg

Menthone is found naturally in many essential oils, such as pennyroyal, peppermint and geranium(1).

Menthone's production and use in perfumes and flavor compositions(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 120(SRC), determined from a water solubility of 688 mg/l(2) and a regression-derived equation(3), indicates that menthone is expected to have high mobility in soil(SRC). Volatilization of menthone from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Menthone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.28 mm Hg(SRC), determined from a fragment constant method(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a water solubility of 688 mg/l(2) and a regression-derived equation(3), indicates that menthone is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.6X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Volatilization half-lives for a model river and model lake are 0.5 and 8 days, respectively(SRC), using an estimation method(3). According to a classification scheme(5), an estimated BCF value of 15(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), menthone, which has an estimated vapor pressure of 0.28 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase menthone 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 14 hours(SRC) from its estimated rate constant of 2.6X10-11 cu cm/molecule-sec(SRC), determined by a fragment constant estimation method(3).

The rate constant for the vapor-phase reaction of menthone with photochemically-produced hydroxyl radicals has been estimated as 2.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 14 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Menthone is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum.

An estimated BCF of 15 was calculated for menthone(SRC), using a water solubility of 688 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of menthone is estimated as approximately 120(SRC), using a water solubility of 688 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that menthone is expected to have high mobility in soil(SRC).

The Henry's Law constant for menthone is estimated as 1.6X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that menthone is expected to volatilize from water surfaces(2). 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)(2) is estimated as approximately 0.5 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)(2) is estimated as approximately 8 days(SRC). Menthone's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces may occur(SRC). Menthone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.28 mm Hg(SRC) determined from a fragment constant method(3).

SURFACE WATER: Menthone was identified, not quantified, in several streams and brooks in Switzerland(1).

Occupational exposure to menthone may occur through inhalation and dermal contact with this compound at workplaces where menthone is produced or used. The general population may be exposed to menthone through dermal contact with perfumes and ingestion of products containing menthone. (SRC)

...KETONES (EG CARVONE & MENTHONE) ARE REDUCED TO SECONDARY ALCOHOLS WHICH ARE THEN EXCRETED AS GLUCURONIDES. MENTHONE, ASYMMETRIC REDUCTION /TO/ NEO-MENTHOL, GLUCURONIDE CONJUGATION /TO/ MENTHYL GLUCURONIDE.

ASSAY: 98% /DL-FORM/; 95% /OPTICALLY ACTIVE FORM/|Note: Apinol obtained by dry distillation of wood of Pinus palustris mill (P australis michx), Pinaceae is chiefly L-menthone... Amber-colored oil, BP about 182.2 °C, density 0.946. /Apinol/

Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2R,5S)-rel-: ACTIVE|L-ISOMENTHONE HAS BEEN IDENTIFIED IN REUNION GERANIUM, PELARGONIUM CAPITATUM, & OTHERS. /L-ISOMENTHONE/|FLAVORS USEFUL IN: TOOTHPASTE FLAVORS, MINT FLAVORS.|NON-ALCOHOLIC BEVERAGES 7.7 PPM; ICE CREAM, ICES 33 PPM; CANDY 71 PPM; BAKED GOODS 52 PPM; CHEWING GUM 8.7 PPM. FEMA 2667.|The menthone isomers have a strong tendency to interconvert and are therefore difficult to obtain in high purity.

PHOTOMETRIC DETECTION CAN BE IMPORTANT PARAMETER IN OPTIMIZING SEPARATION OF ESSENTIAL OIL CONSTITUENTS.|TWO METHODS WERE USED TO DETECT MENTHONE IN ESSENTIAL OILS, SILYLATION (OF HYDROXY COMPD) FOLLOWED BY GAS CHROMATOGRAPHY-MASS SPECTROMETRY & EXTRACTION WITH GIRARD D REAGENT FOLLOWED BY GAS CHROMATOGRAPHY.

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index

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