4-(2,6,6-Trimethylcyclohex-2-en-1-yl)-but-3-en-2-on

It has a warm, woody, floral odor with balsamic and sweet tones and is strongly reminiscent of violet flowers.

Sweet-floral odor, reminiscent of violets

0.9319 at 20/4 °C

0.927-0.933

In water, 106 mg/L at 25 °C

Soluble in alcohol, most fixed oils, propylene glycol; insoluble in glycerin

Miscible with absolute alcohol. Soluble in 2 to 3 parts of 70% alcohol, ether, chloroform, benzene. Very slightly soluble in water. /mixed ionone isomers/

soluble in alcohol, propylene glycol, most fixed oils; insoluble in glycerol and water

1 ml in 3 ml 70% alcohol; 1 ml in 10 ml 60% alcohol (in ethanol)

258 °C at 760 mm Hg

Pale yellow to yellow liquid; Specific gravity: 0.933-0.937 25/25 °C; Boiling point: 126-128 °C at 12 mm Hg /mixed ionone isomers/

237 °C

Not Classified

Aggregated GHS information provided per 1789 reports by companies from 10 notifications to the ECHA C&L Inventory.

Warning

H315: Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P272, P280, P302+P352, P321, P332+P317, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Danger

Chemical: 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (E)-

Regulation (EC) No 1831/2003 (amended)

3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (3E)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (3E)- 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: 25-07-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/18612

alpha-Ionone: Does not have an individual approval but may be used under an appropriate group standard

alpha-Ionone 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 b) 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.

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.

Not Classified

Skin irritation - category 2

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

Extinguishing methods: Alcohol foam. Water or foam may cause frothing.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas.; Environmental precautions: Do not let product enter drains.; Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Contaminated packaging: Dispose of as unused product.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Normal measures for preventive fire protection.

Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

Skin protection: Handle with gloves.

Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 670(SRC), determined from a structure estimation method(2), indicates that alpha-ionone is expected to have low mobility in soil(SRC). Volatilization of alpha-ionone from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.5X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.019 mm Hg(3), and water solubility, 106 mg/L(4). alpha-Ionone, a perfumery compound with an odor(5), is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). The biodegradability of alpha-ionone is expected to be analogous to beta-ionone(SRC) which was found to be readily biodegradable by two OECD screening tests(6). A 79% of theoretical BOD using activated sludge in the OECD 301F test(6) suggests that biodegradation is an important environmental fate process in soil(SRC). beta-Ionone was also classified as readily biodegradable by the results of a CO2-evolution test where beta-ionone achieved 46% and 73% CO2 evolution after 7 and 28 days, respectively(6). By analogy to beta-ionone(7), alpha-ionone is expected to absorbs at wavelengths >290 nm and, therefore, may be susceptible to direct photolysis on soil surfaces exposed to sunlight(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 670(SRC), determined from a structure estimation method(2), indicates that alpha-ionone is 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 4.5X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.019 mm Hg(4), and water solubility, 106 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 31 hours and 13 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 161(SRC), from its log Kow of 3.85(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). The biodegradability of alpha-ionone is expected to be analogous to beta-ionone(SRC) which was found to be readily biodegradable by two OECD screening tests(8). A 79% of theoretical BOD using activated sludge in the OECD 301F test(8) suggests that biodegradation is an important environmental fate process in water(SRC). beta-Ionone was also classified as readily biodegradable by the results of a CO2-evolution test where beta-ionone achieved 46% and 73% CO2 evolution after 7 and 28 days respectively(8). In a spiked river water die-away test, beta-ionone, at 6.28 ug/L, was degraded about 95% after 20 hours of incubation(8). alpha-Ionone is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). alpha-Ionone is an olefin and olefins in surface waters exposed to sunlight react with photo-oxidants (such as hydroxyl radicals, peroxy radicals and singlet oxygen) with a half-life on the order of 25 days(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), alpha-ionone, which has an extrapolated vapor pressure of 0.019 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase alpha-ionone 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 2.7 hours(SRC), calculated from its rate constant of 1.5X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase alpha-ionone is also degraded in the atmosphere by reaction with ozone and nitrate radicals(SRC); the half-lives for these reaction in air are estimated to be 14 and 0.8 hours respectively(SRC), calculated from analogous measured rate constants for beta-ionone of 1.9X10-17 cu cm/molecule-sec at 24 °C for ozone(4) and 9.4X10-12 cu cm/molecule-sec at 24 °C for nitrate radicals(5). The nitrate radical (NO3) is the dominant atmospheric oxidant during the night-time in most atmospheric environments(6), therefore, night-time degradation appears to be a major fate process for alpha-ionone(SRC). By analogy to beta-ionone(SRC), which absorbs strongly at wavelengths >290 nm(7), alpha-ionone may be susceptible to direct photolysis by sunlight(SRC).

IDENTIFICATION AND USE: Alpha-ionone (AI) is a colorless to slightly yellow liquid. AI is a fragrance ingredient in perfumery, in cosmetics and personal care products, in household cleaners and detergents. Flavoring agent in beverages, baked goods, and candies. Used as an ingredient in dog/cat repellent. It is registered for pesticide use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. HUMAN EXPOSURE AND TOXICITY: AI (32 % in acetone) was found to be a moderate irritant. No reactions were observed with 1% AI; 5% AI produced one irritant/questionable reaction. ANIMAL STUDIES: No skin irritation was observed in miniature swine using neat AI. In guinea pigs AI was reported to be moderately irritating in skin test. AI produced severe skin irritation reaction in rabbits. AI was tested in a 90-days oral toxicity study using male and female rats. Body weigh gains and feed intake were reduced slightly in both males and females (10 mg/kg). In rats diet containing mixture of AI (60%) and beta-ionone produced swelling of hepatic parenchymal cells after 17 weeks. No mutagenic activity was observed in Salmonella typhimurium strains TA98 and TA100 when treated with AI at concentrations up to approximately 50 ug/plate with and without metabolic activation. AI at 25 mM concentration caused significant increases in chromosome aberrations in Chinese hamster cells. A micronucleus test in mice was negative.

alpha- and beta-Ionone account for 57% of the volatile components of violet flowers (Viola odorata)(1). alpha-Ionone is reported to occur in apricot, orange peel oil, grapefruit juice, raspberry, blackberry, carrot, celery leaves and seed, peas, tomato, tea, beans,and loganberry(2). Apricots (Prunus armeniaca L.) were found to contain alpha-ionone at a concentration of 10 ug/kg of fresh fruit tissue(3). alpha-Ionone was detected in paprika oleoresin at a concentration of 0.4 mg/kg(4).

alpha-Ionone detections in plants(1).[Table#8258]

Using a structure estimation method based on molecular connectivity indices(1), the Koc of alpha-ionone can be estimated to be 670(SRC). According to a classification scheme(2), this estimated Koc value suggests that alpha-ionone is expected to have low mobility in soil.

/HUMAN EXPOSURE STUDIES/ A 48-hr occluded patch test was conducted on the backs of 50 adult male volunteers. A 0.05 g aliquot of 32% alpha-ionone in acetone was placed on 15 mm patches which were then applied to the back of each subject for 48 hr. The patches were removed and the sites were swabbed with dry gauze to remove residual test material. Reactions were evaluated at 30 min after patch removal and if necessary, at 72, 96 and 120 hr after patch removal. alpha-ionone was found to be a moderate irritant.

/HUMAN EXPOSURE STUDIES/ In a multicenter study, /researchers/ reported the results of patch tests with 48 fragrance materials. alpha-Ionone at 1% and 5% in petrolatum was tested in 86 male and 119 female patients. alpha-Ionone was applied to the back for 48 hr using Finn chambers on Scanpor tape. Reactions were assessed per ICDRG /(International Contact Dermatitis Research Group)/ guidelines on days 2 and 3 or on days 2 and 4. No reactions were observed with 1% alpha-ionone; 5% alpha-ionone produced one irritant/questionable reaction.

alpha-Ionone's production and use in perfumery(1) and as a flavoring compound in foods(2) may result in its release to the environment through various waste streams(SRC). Its use as a fragrance ingredient in perfumery, in cosmetics and personal care products, in household cleaners and detergents(3) and as an ingredient in dog/cat repellent used on plants and lawn furniture(4) will result in its direct release to the environment(SRC). alpha-Ionone has been identified as a component of tobacco smoke(5).

AEROBIC: The biodegradability of alpha-ionone is expected to be analogous to beta-ionone(SRC). Using the OECD 301F method (manometric respirometry) with an activated sludge inoculum, beta-ionone, at 50 mg/L, reached 79% of its theoretical BOD in 28 days which classified the compound as readily biodegradable(1). beta-Ionone was also classified as readily biodegradable by the results of a CO2-evolution test where beta-ionone, at 10 mg/L, achieved 46% and 73% CO2 evolution after 7 and 28 days respectively(1). Another respirometry study reported 80% biodegradation of beta-ionone at 100 mg/L(2). In a spiked river water die-away test using water from the Murrumbidgee River, beta-ionone, at 6.28 ug/L, was degraded about 95% after 20 hours of incubation(1). Results of a modified MITI test (OECD 301C) reported 50% degradation of beta-ionone after 28 days (consistent with inherent biodegradability), but concentrations or inoculum were not reported(1).

alpha-Ionone 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 b) 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.

For alpha-ionone (USEPA/OPP Pesticide Code: 129030) ACTIVE products with label matches. /SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Reported uses (ppm):

Fragrance ingredient in perfumery, in cosmetics and personal care products, in household cleaners and detergents. Flavoring agent in beverages, baked goods, and candies.

Used as an ingredient in dog/cat repellent; attracts adult rose chafers (a beetle).

2023: 100,000 - <250,000 lb

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (3E)-. National Production Volume: Withheld.

Scent-Off Pellets (Baker's & 18 Corporation): Active ingredient: Oil of mustard 0.20%; Oil of citronella 1.20%; Oil of lemongrass 2.00%; Oil of orange 0.02%; Methyl salicylate 0.02%; Bergamot oil 0.11%; 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (E)- 0.01%; and Geraniol 0.04%.

Scent-Off Aroma Pouches (Baker's & 18 Corporation): Active ingredient: Oil of mustard 0.20%; Oil of citronella 1.20%; Oil of lemongrass 2.00%; Oil of orange 0.02%; Methyl salicylate 0.02%; Bergamot oil 0.11%; 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (E)- 0.01%; and Geraniol 0.04%.

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (3E)-: ACTIVE

... Alpha- and beta-ionones account for 57% of the volatile components of violet flowers (Viola odorata).