Acetoin

88.11

88.11

385636

208-174-1

89727|7609

2621

DTXSID0024399

Slightly yellow liquid or crystals

29144090

37.3

-0.36 /Estimated/

Pale yellow to green-yellow or white to yellow Liquid (Monomer) or Powder or Crystals (Dimer)

0.9972 g/cm³ @ Temp: 17 °C

15 °C

148 °C @ Press: 760 Torr

123 °F

1.408

H2O: soluble

2-8°C

2.7x10 (est)

Oral-Rat LD50: >5000 mg/kg

Combustible in case of fire, high temperature and strong oxidant

OPTICALLY ACTIVE COMPD; OPTICAL ROTATION: -39.4 DEG (PURE) AND -105 DEG (AQ SOLN) AT 20 °C

Buttery odor

FATTY CREAMY "TUB" BUTTER TASTE

1.03e-11 cm3/molecule*sec

Henry's Law constant = 1.0X10-5 atm-cu m/mol at 25 °C /Estimated/

Reduces Fehling's solution forming acetic acid.|SLIGHTLY SOL IN ALCOHOL; SOL IN ACETONE; MAX ABSORPTION (WATER): 272.5 NM (LOG E= -0.5); SADTLER REF NUMBER: 7362 (IR, PRISM); 2086 (UV); 536 (NMR); INDEX OF REFRACTION: 1.4171 @ 20 °C/D; DENSITY: 1.0062 AT 20 °C/20 °C /DL/|UV: 2086 (Sadtler Research Laboratories Spectral Collection) /2-Butanone, 3-hydroxy (dl)/|Hydroxyl radical reaction rate constant = 1.0X10-11 cu cm/molec sec at 23 °C

Flammable. Slightly soluble in water.

Alcohols and Polyols

ACETYL METHYL CARBINOL is a ketone and alcohol. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

III

3

UN 2621 3/PG 3

1

10-36/38-38-11

26-36-36/37

EL8790000

Xi,F

Complete packaging, light loading and unloading; warehouse ventilated, away from open flame, high temperature, and stored separately from oxidant

Oxidizes gradually to diacetyl on exposure to air.

P305 + P351 + P338

H226-H315-H319

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.

Synthetic flavoring substances and adjuvants /for human consumption/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Acetoin is included on this list.|Synthetic flavoring substances and adjuvants /for animal drugs, feeds, and related products/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Acetoin is included on this list.

A REVIEW WITH DISCUSSION ON TOXICITY, SENSITIZATION, METABOLISM, CARCINOGENICITY, PHARMACOLOGY, ENZYMES EFFECT & EFFECT ON ISOLATED TISSUES.[OPDYKE DL J; MONOGRAPHS ON FRAGRANCE RAW MATERIALS. ACETOIN; FOOD COSMET TOXICOL 17(5) 509 (1979)]

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016)|Flammable - 2nd degree

|Warning|H226 (26.95%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P264, P280, P302+P352, P303+P361+P353, P305+P351+P338, P321, P332+P313, P337+P313, P362, P370+P378, P403+P235, and P501|Aggregated GHS information provided by 1770 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory.|H226: Flammable liquid and vapor [Warning Flammable liquids]

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: CAUTION: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient. CAUTION: For fire involving UN1170, UN1987 or UN3475, alcohol-resistant foam should be used. SMALL FIRE: Dry chemical, CO2, water spray or alcohol-resistant foam. LARGE FIRE: Water spray, fog or alcohol-resistant foam. Do not use straight streams. Move containers from fire area if you can do it without risk. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2016)

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). 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)

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)

Flammable liquid

/GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.|/GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Health: Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control may cause pollution.|/GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.|/GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.|For more DOT Emergency Guidelines (Complete) data for ACETOIN (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

practically nontoxic

LD50 Rat oral >5000 mg/kg bw /from table/

Based on cell free suspensions of several acetic acid bacteria, 2,3-butanediol is expected to oxidize to acetoin(1).

PHOTOCHEMICAL AEROSOL FORMATION OF SYSTEM SO2-NO-CIS-2-BUTENE AIR STUDIED. 1 PRODUCT OF PHOTOOXIDATION OF CIS-2-BUTENE WAS ACETOIN.|Acetoin's production and use as a fragrance carrier and in the preparation of flavors and fragrances(1) may result in its release to the environment through various waste streams.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2(SRC), determined from a water solubility of 1.0X10+6 mg/L(2) and a regression-derived equation(3), indicates that acetoin is expected to have very high mobility in soil(SRC). Volatilization of acetoin from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.0X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Acetoin is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.7 mm Hg(SRC), determined from a fragment constant method(5). Theoretical BOD values ranging from 2.6-13.8% following aerobic incubation from 6 to 24 hrs using activated sludge, indicate that biodegradation is an important environmental fate process in soil(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2(SRC), determined from a water solubility of 1.0X10+6 mg/L(2) and a regression-derived equation(3), indicates that acetoin 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 1.0X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 and 28 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 0.3(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). %BODT values ranging from 2.6-13.8 following aerobic incubation for 6, 12, and 24 hrs using activated sludge, indicate that biodegradation is not an important environmental fate process in water(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acetoin, which has an estimated vapor pressure of 2.7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase acetoin 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 37 hrs(SRC), calculated from its rate constant of 1.0X10-11 cu cm/molecule-sec at 25 °C(3). Acetoin is not expected to undergo photolysis due to the lack of absorption in the environmental UV spectrum(>290 nm)(SRC).

The rate constant for the vapor-phase reaction of acetoin with photochemically-produced hydroxyl radicals is 1.03X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 37 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). Acetoin 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).

An estimated BCF of 0.3 was calculated for acetoin(SRC), using a water solubility of 1.0X10-6 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 acetoin is estimated as 2(SRC), using a water solubility of 1.0X10+6 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that aetoin is expected to have very high mobility in soil.

The Henry's Law constant for acetoin is estimated as 1.0X0-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that acetoin 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 2 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 28 days(SRC). Acetoin's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Acetoin is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.7 mm Hg(SRC), determined from a fragment constant method(3).

PRESENT IN CORN, WINE, VINEGAR (FROM GRAPE OR OTHER SOURCES), HONEY, COCOA, BUTTER, AND ROASTED COFFEE; IDENTIFIED ALSO IN CURRANT AND STRAWBERRY AROMAS.|A study of rice cakes in 1999 found that two leading brands of rice cakes contained 600 and 750 ppb of acetoin(1), respectively. Australian honey was found to contain between 0.5 and 6.9 mg/kg of acetoin in a 1997 study(2). A study of 4 species of nectarines in 1988 found acetoin was present in less than 10 mg/kg quantities(3). Acetoin was detected in flavored bacon during a study in 1983, no specific details were provided(4). In Japan a study was conducted on beef, soy sauce and sake in 1981, all three food components contained acetoin in measurable quantities, no concentrations were reported(5).

Occupational exposure to acetoin may occur through inhalation and dermal contact with this compound at workplaces where acetoin is produced or used. The general population may be exposed to acetoin via inhalation of perfume and fragrance vapors, dermal contact, and ingestion of food products containing this compound. (SRC)

In rats and mice, orally administered aliphatic alpha-diketones are rapidly absorbed from the gastrointestinal tract. Carbon dioxide produced primarily from methyl-substituted diketones (e.g. diacetyl) is eliminated in expired air. Thus, after injection of [2,3-14C]-acetoin to whole albino rats, 14C-carbon dioxide appeared in expired air, with an average 12-hr production of 15%.|A total dose of 78 g of acetoin was administered to a dog over 2 months, both orally in a 3-4% solution and subcutaneously in a 20% solution. Urine was collected under toluene from the beginning of treatment up to 40 hr after the last dose. 2,3-Butanediol was the major urinary excretion product, representing 5-25% of the dose. The remainder of the dose was completely metabolized.|Acetoin was given either orally in a 3-4% solution or subcutaneously in a 20% solution to rats, multiple doses being spaced equally throughout each day. The acetoin used was obtained as the polymer (H, 15), which apparently reverts to an optically inactive monomer in aqueous solution. No diacetyl was detected in the urine of the rats; acetoin was not excreted to any appreciable extent in the urine, and the major excretion product was 2,3-butanediol. In dogs, acetoin is excreted in the urine, in part as 2,3-butanediol. Most of an oral dose disappeared and was presumed to be completely metabolized. In another study, 2,3-butanediol readily conjugated glucuronic acid.

In liver preparations obtained from rats and rabbits, more than 95% of the radiolabel of [2,3-14C]-acetoin was detected as a mixture of stereoisomers of 2,3-butanediol. Although reduction of diacetyl and acetoin has been observed in animals in vivo and in animal tissue preparations in vitro at high concentrations, it appears that oxidation of diacetyl is a major endogenous metabolic pathway.|Acetoin is metabolized primarily via oxidation at low concentrations in vivo and by reduction to 2,3-butanediol at high concentrations. It has been estimated that 1 g of rat liver can oxidize 86 ug (1 umol) acetoin per day. Production of carbon dioxide at low levels and of 2,3-butanediol at high levels is associated with the slower rate of ketone reduction. Oxidation of the terminal methyl group may result in formation of an alpha-ketoacid, which undergoes cleavage to yield carbon dioxide and a carboxylic acid fragment. Alternatively, methyl group oxidation may yield a beta-ketoacid which undergoes beta-cleavage to yield two-carbon fragments. To a minor extent, these two-carbon fragments can act as acetyl donors for acetylation of para-aminobenzoic acid.

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control may cause pollution. (ERG, 2016)

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Keep victim calm and warm. (ERG, 2016)

Basic treatment: Establish a patent airway. 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 normal saline 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 ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

/OTHER TOXICITY INFORMATION/ Diacetyl and acetoin are endogenous in humans. They are formed when pyruvate is converted to acetoin and diacetyl by pyruvate decarboxylase. Mean fasting blood concentrations of approximately 100 ug acetoin per 100 mL blood have been reported.

3-hydroxy-2-butanone

GRADES: Technical, FCC (as Acetoin).

2-Butanone, 3-hydroxy-: ACTIVE|Non-alcoholic beverages 7.4 ppm; ice cream, ices, etc 3.3 ppm; candy 18 ppm; baked goods 32 ppm; gelatins & puddings 0.60-21 ppm; shortening 8.0 ppm; margarine 0.80-50 ppm; cheese (cottage) 70 ppm.|...Useful /as flavor/ in butter, milk, yogurt, strawberry.

BLOOD CONCN OF 3-HYDROXY-2-BUTANONE WERE DETERMINED BY GAS CHROMATOGRAPHY.

Food additives -> Flavoring Agents|Fatty Acyls [FA] -> Oxygenated hydrocarbons [FA12]|Fire Hazards -> Flammable - 2nd degree

Flavoring Agents