Acetoin

Other Uses -> Food Additives

Flammable agents - 2nd degree

log Kow = -0.36 /Estimated/

-0.360

Buttery odor

BLAND, WOODY, YOGURT ODOR

0.9972 g/cu cm at 17 °C

1.005-1.019

Sparingly soluble in ether, petroleum ether

Soluble in alcohol, slightly soluble in ether.

Miscible with alcohol, propylene glycol; insoluble in vegetable oil

Miscible in water.

1000 mg/mL at 20 °C

insoluble in vegetable oils; miscible with alcohol, water, propylene glycol

41 °C

106 °F

106 °F

Danger

H226 (26.6%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P264, P264+P265, P280, P302+P352, P303+P361+P353, P305+P351+P338, P305+P354+P338, P317, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1832 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Not Classified

Warning

Chemical: 2-Butanone, 3-hydroxy-

Regulation (EC) No 1831/2003 (amended)

2-Butanone, 3-hydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Butanone, 3-hydroxy- 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: 08-07-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/28356

2-Butanone, 3-hydroxy-: HSNO Approval: HSR001074 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

· Inhalation or contact with material may irritate or burn skin and eyes.

A fermentation product; Oxidized in mammals to carbon dioxide; [ChemIDplus] Endogenously formed in humans by pyruvate conversion; Intraperitoneal injection in rats caused intoxication similar to ethyl alcohol; Increased liver weights in rats after subchronic feeding studies; Oral LD50 (rat) >5000 mg/kg; [HSDB] May cause irritation or burns to skin and eyes; [CAMEO] An irritant; [MSDSonline]

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.

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.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

General First Aid:

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.

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

Immediate precautionary measure

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).

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).

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=513-86-0]

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.

/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.

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.

AEROBIC: Three activated sludges from Columbus, Hilliard, and Linwood, OH wastewater treatment plants were used as inocula in Warburg respirometer tests designed to measure oxygen uptake of acetoin(1). The suspended solids concentration was adjusted to 2,500 mg/L; acetoin was added to obtain a concentration of 500 mg/L and incubated at 20 °C. Average theoretical BOD values measured at 6, 12 and 24 hours were 2.6, 4.3, and 13.8%, respectively, indicating that biodegradation is an important fate process(1).

ANAEROBIC: Acetoin was added at a concentration of 50 ppm C to sludges from secondary digesters in Adrian and Jackson, MI. The sludges were diluted to 10% and incubated anaerobically in 160-ml serum bottles for 56 days at 35 °C(1). Acetoin was mineralized >75% after 8 weeks(1), indicating the compound is susceptible to anaerobic biodegradatoin following acclimation(1).

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 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).

/LABORATORY ANIMALS: Acute Exposure/ The toxicity of acetoin in rats was investigated and compared to ethyl-alcohol. Small (unspecified) amounts of a 30% acetoin solution or ethyl-alcohol were injected ip into rats until the loss of the righting reflex or until respiratory failure. In another series, 5 mg/kg methyl-alcohol was injected, followed by acetoin until respiratory failure was induced. Blood was drawn and analyzed for the compounds. With loss of righting reflex, acetoin ranged from 227 to 251 mg percent with an average of 235 mg. Ethyl-alcohol ranged from 288 to 312 mg with an average of 300 mg. Acetoin intoxication resembled ethyl-alcohol intoxication. Upon respiratory failure, acetoin concentrations ranged from 742 to 770 mg percent with an average of 754 mg. Ethyl-alcohol ranged from 900 to 952 mg percent with an average of 920 mg. With combined administration, the concentrations of acetoin and ethyl-alcohol in the blood were additive in effect. The author concludes that acetoin is 1.4 times more intoxicating than ethyl-alcohol.

/LABORATORY ANIMALS: Acute Exposure/ The effect of uremic toxins on oxygen consumption (OC) was studied. Male Sprague-Dawley-rats were injected intraperitoneally with acetoine. Rats were starved before and after administration of chemicals. OC was measured between 1 and 6 hours after treatment using a diaferometer or a digital respirometer. ...In-vitro OC of rat diaphragma and liver slices was measured in a Warburg apparatus using Krebs phosphate buffer at pH 7.4. ...Acetoine at 3600 mg/kg had no influence on OC. ...No decrease in blood pressure was observed. Injection of 3600 mg/kg of acetoine made them comatose for several hours. Liver slices and diaphragms from normal or uremic rats showed a normal metabolic rate. Exposure to compounds at 30 mg/dL had no influence on tissue respiration. Addition of 400 mg/dL of urea and 20 mg/dL of creatinine had no influence on OC when given alone or in combination with chemicals.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ No-untoward-effect level of acetoin was established as 3000 ppm in drinking water to rats. Levels admin were 0, 750, 3000 or 12,000 ppm for 13 wk. At 12,000 ppm body wt gain was reduced, which was assoc with redn in food & water intake. Liver wt incr. Slight anemia reported.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Groups of 15 male and 15 female CFE rats were given acetoin in their drinking-water at concentrations of 0 (control), 750, 3000, or 12,000 mg/kg (equivalent to 0, 85, 330, or 1300 mg/kg bw/day). No animals died during the study, and their condition and appearance were normal. The body weights of males at 12,000 mg/kg in drinking-water decreased significantly from week 5, and at weeks 2, 6, and 13 the relative weight of the liver was statistically significantly greater in these animals than in controls. A similar effect was seen in female rats, but only after 13 weeks. Hematological examination conducted at 13 weeks showed a small (4-8%) but statistically significant (p<0.05) decrease in hemoglobin concentration and erythrocyte counts in animals of each sex at the high dose, but these changes were not accompanied by a decrease in hematocrit. Urinalysis and blood chemical determinations performed at the end of the study on all animals revealed no statistically significant differences between treated and control groups. Histopathological examination also revealed no adverse effects. ...The increased relative liver weights /may have been/ a reaction of the liver to an increased metabolic load resulting from the high intake of acetoin. The NOEL was 3000 ppm, equivalent to 330 mg/kg bw/day.

/GENOTOXICITY/ Acetoin /(at </=4500 mg/plate)/, diacetyl, and 1,2-cyclohexanedione showed some mutagenicity in /Salmonella typhimurium/ strains TA100 and TA104. As the mutation frequencies were low and the positive results were always accompanied by negative results, the overall conclusion was that this group of substances does not induce gene mutation in bacteria in vitro.

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.

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.

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.

Used as a carrier for aromas and flavors; [Hawley]

Aroma carrier; prepn of flavors & essences

... Used for flavoring margarine.

A product of fermentation, also in cream ripened for churning. Obtained by the action of sorbose bacteria or Mycoderma aceti on 2,3-butanediol or by the action of fungi, such as Aspergillus, Penicillium, Mycoderma on sugar cane juice.

From diacetyl by partial reduction with Zn and acid

Acetoin is an optically active compd. The d (-) acetyl methyl carbinol is obtained from fermentation and in mixture with other products, from the catalytic oxidation of 2,3-butanediol.

Acetoin is an optically active compd. The l (+) acetyl methyl carbinol is obtained from fermentation. The optically pure form has not been isolated; the optically inactive form is prepared synthetically.

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

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.