α-Ionone

192.3

192.30

2046084

204-841-6

34560

DTXSID0035160

Colorless to slightly yellow liquid

29142300

17.1

3.85

Liquid

0.9319 g/cm³ @ Temp: 20 °C

<25 °C

131 °C

230 °F

n 20/D 1.498(lit.)

H2O: insoluble ;soluble in ethanol fixed oils, propylene glycol. Slightly soluble in alcohol, ether, mineral oil.

2-8°C

0.019 mm Hg at 25 C (extrapolated from higher temperatures)

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

Woody, floral, berry, fruity with powdery nuances

Henry's Law constant = 4.5X10-5 atm-cu m/mole at 25 °C (est)

Both optical isomers of alpha-ionone are found in nature. Generally, ionones have a trans configuration. trans-alpha-Ionone can be converted into the cis-isomer by exposure to ultraviolet light.|Hydroxyl radical reaction rate constant = 1.5X10-10 cu cm/molec-sec at 25 °C (est)

II; III

4.1

NONH for all modes of transport

2

42-36-36/37/38

36-24/25-26-36/37/39-27

EN0525000

Xn,Xi

Stable under recommended storage conditions.

P261-P342 + P311

H334

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.

Incompatible materials: Strong oxidizing agents.

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.

Not Classified| |Warning|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P280, P302+P352, P321, P332+P313, P333+P313, P362, P363, and P501|Danger|H334: May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]|P261, P285, P304+P341, P342+P311, and P501

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).

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.

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.

alpha-Ionone was found to be a moderate /skin/ irritant.

| 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.

SEDIMENT: alpha-Ionone was qualitatively detected in sediment collected in the German Bight, near the Elbe River, in 1998(1).

alpha-Ionone has been identified as a component of tobacco smoke(1). It is a component of bitter orange extract(2).

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.

LD50 Mouse i.p 2,277 mg/kg|LD50 Mouse s.c 2,605 mg/kg

Both optical isomers of alpha-ionone are found in nature(1). alpha-Ionone occurs widely in plants, such as, in violets, blackberries, plums, and tobacco(2).

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).

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).

The rate constant for the vapor-phase reaction of alpha-ionone with photochemically-produced hydroxyl radicals has been estimated as 1.5X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of alpha-ionone with atmospheric ozone is expected to similar to the measured value for beta-ionone(SRC), 1.9X10-17 cu cm/molecule-sec at 24 °C(2); this corresponds to an atmospheric half-life of about 14 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(1). The rate constant for the vapor-phase reaction of alpha-ionone with atmospheric nitrate radicals is expected to similar to the measured value for beta-ionone(SRC), 9.4X10-12 cu cm/molecule-sec at 24 °C(3); this corresponds to an atmospheric half-life of about 0.8 hours(SRC) at an atmospheric concentration of 2.5X10+8 nitrate radicals per cu cm(4). The nitrate radical (NO3) is the dominant atmospheric oxidant during the night-time in most atmospheric environments(5), 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(6), alpha-ionone may be susceptible to direct photolysis by sunlight(SRC). alpha-Ionone is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(7). 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(8).

An estimated BCF of 161 was calculated in fish for alpha-ionone(SRC), using a log Kow of 3.85(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC).

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.

The Henry's Law constant for alpha-ionone is estimated as 4.5X10-5 atm-cu m/mole(SRC) derived from its extrapolated vapor pressure, 0.019 mm Hg(1), and water solubility, 106 mg/L(2). This Henry's Law constant indicates that alpha-ionone 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 31 hours(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 13 days(SRC). alpha-Ionone's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). alpha-Ionone, a perfumery compound with an odor(4), is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

GROUNDWATER: Groundwater sampled from a contaminated industrial site in Spain contained ionone (isomers not specified) concentrations of 28-655 ng/L(1).

In addition to a variety of fruits, alpha-ionone has detected in peas, cognac, rum, whiskies, white wines, tea, beans, buck wheat, and brandy(1). alpha-Ionone was detected in popcorn at a concentration of 2 ug/kg(2).

According to the 2012 TSCA Inventory Update Reporting data, 4 reporting facilities estimate the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of alpha-ionone (127-41-1) and ionone, mixed isomers (8013-90-9) may be as low as 10-24 workers up to the range of 50-99 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 40,007 workers (11,154 of these were female) were potentially exposed to ionone (CAS 8013-90-9; mixed isomers) in the US(1). Occupational exposure to alpha-ionone may occur through inhalation and dermal contact with this compound at workplaces where alpha-ionone is produced or used. Monitoring and use data indicate that the general population may be exposed to alpha-ionone via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with consumer products containing beta-ionone(SRC).

Following oral administration, alpha-ionone undergoes biochemical oxidation in the rabbit and is excreted in the urine, principally, as 5-oxo-cis-tetrahydro-ionone, indicating in vivo oxidation of carbon atom 5 in the ionone structure.

Two rabbits were fed a single dose of 170 g of pure alpha-ionone. Urine was collected and ether soluble compounds were extracted. The major urinary metabolite was identified as 5-oxo-cis-tetrahydroionone.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/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

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%.

All other chemical product and 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).

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