HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Acetoin
AMC · 3-HYDROXY-2-BUTANONE · 3-HYDROXYBUTAN-2-ONE · ACETYL METHYL CARBINOL · acetoine · Acetion · (S)-Acetoin · FEMA 2008
Identifikatoren & physikalische Daten
| CAS No. | 513-86-0 |
|---|---|
| Summenformel | C4H8O2 |
| Durchschnittliche Molmasse | 88,11 g/mol |
| Monoisotopische Masse | 88,0524295 g/mol |
| SMILES | CC(=O)C(C)O |
| InChIKey | ROWKJAVDOGWPAT-UHFFFAOYSA-N |
| PubChem CID | 179 |
| ChEMBL | CHEMBL3561873 |
| ChEBI | CHEBI:15688 |
| EC No. | 208-174-1 |
| DTXSID | DTXSID0024399 |
| Lokaler Name | Acetoin |
Chemische & physikalische Eigenschaften
| XLogP | -0,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 37,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 6 |
| Formalladung | 0 |
| Komplexität | 58,6 |
| Stoffklassen | Other Uses -> Food AdditivesFlammable agents - 2nd degree |
| Lipide | Fatty Acyls [FA] -> Oxygenated hydrocarbons [FA12] |
| Duftstoffe | Fragrance Ingredient (Acetoin) -> IFRA transparency List |
| LogP (Verteilungskoeffizient) | log Kow = -0.36 /Estimated/-0.360 |
| Geruch | Buttery odorBLAND, WOODY, YOGURT ODOR |
| Geschmack | FATTY CREAMY "TUB" BUTTER TASTE |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 0.9972 g/cu cm at 17 °C1.005-1.0191.013 g/mL at 25 °C(lit.) |
| Aromastoffe | EU Flavoring substances |
| Color/Form | Slightly yellow liquid or crystals |
| Löslichkeit | Sparingly soluble in ether, petroleum etherSoluble in alcohol, slightly soluble in ether.Miscible with alcohol, propylene glycolinsoluble in vegetable oilMiscible in water.1000 mg/mL at 20 °Cinsoluble in vegetable oilsmiscible with alcohol, water, propylene glycolAll forms are miscible with water, alcohol, Propylene glycol, Glycerine and common flavor materials. Poorly soluble in hydrocarbons.H2O: 0.1g/mL, clear |
| Flammpunkt | 41 °C106 °F123 °F |
| Schmelzpunkt | 15 °C (monomer) |
| Siedepunkt | 148 °C(lit.) |
| Dampfdruck | 86hPa at 20℃ |
| FEMA | 2008 | ACETOIN |
| Brechungsindex | n20/D 1.417(lit.) |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | 13.21±0.20(Predicted) |
| Aggregatzustand | Liquid (Monomer) or Powder or Crystals (Dimer) |
| Farbe | Pale yellow to green-yellow or white to yellow |
| Geruch | Intensely creamy-fatty-buttery, penetrating odor, yet milder and less “quinone’’-like than Diacetyl, not as sharp or volatile. Pleasant in extreme dilution. |
| Biologische Quelle | synthetic |
| Geruchsart | buttery |
| JECFA Number | 405 |
| Merck | 14,64 |
| BRN | 385636 |
| Henry-Konstante | 3.1×100 mol/(m3Pa) at 25℃, Wu et al. (2022) |
| Stabilität | Hygroscopic |
| Hauptanwendungen | flavors and fragrances |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMING |
| InChI | 1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3 |
| InChIKey | ROWKJAVDOGWPAT-UHFFFAOYSA-N |
| SMILES | CC(O)C(C)=O |
| LogP (Verteilungskoeffizient) | 0.1 at 25℃ |
| CAS Datenbank | 513-86-0(CAS DataBase Reference) |
| NIST chemische Informationen | 2-Butanone, 3-hydroxy-(513-86-0) |
| EPA chemische Informationen | 2-Butanone, 3-hydroxy- (513-86-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH226 (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 |
|---|---|
| Regulatorische Informationen | 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/283562-Butanone, 3-hydroxy-: HSNO Approval: HSR001074 Approved with controlsThe 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.) |
| Weitere Sicherheitsinformationen | Evaluation - Acetoin, cinnamaldehyde, diethylene glycol and ethylene glycol with end use in non-nicotine e-cigarettes (vaping products) |
| DOT-Kennzeichnung | Flammable Liquid Flammable Solid |
| Brandgefahren | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. |
| Brandpotenzial | Flammable liquid |
| Gesundheitsgefahren | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:· Inhalation or contact with material may irritate or burn skin and eyes. |
| Gefahrenübersicht | A fermentation productOxidized in mammals to carbon dioxide[ChemIDplus] Endogenously formed in humans by pyruvate conversionIntraperitoneal injection in rats caused intoxication similar to ethyl alcoholIncreased liver weights in rats after subchronic feeding studiesOral LD50 (rat) >5000 mg/kg[HSDB] May cause irritation or burns to skin and eyes[CAMEO] An irritant[MSDSonline] |
| DOT-Nummer und Handbuch | 2621 127 |
| FDA-Anforderungen | 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. |
| Reaktive Gruppe | Alcohols and Polyols |
| Special Reports | A REVIEW WITH DISCUSSION ON TOXICITY, SENSITIZATION, METABOLISM, CARCINOGENICITY, PHARMACOLOGY, ENZYMES EFFECT & EFFECT ON ISOLATED TISSUES.[OPDYKE DL JMONOGRAPHS ON FRAGRANCE RAW MATERIALS. ACETOINFOOD COSMET TOXICOL 17(5) 509 (1979)] |
| Reactivity Profile | 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. |
| Brandbekämpfung | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: |
| Freisetungsmaßnahmen | · 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. |
| Erste Hilfe | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:General First Aid: |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Freisetung ohne Brand | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Isolation and Evacuation | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:Immediate precautionary measure |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: |
| Emergency Response Planning Guidelines | CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient. |
| Umweltverhalten | 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). |
| Lebensmitteluntersuchungswerte | PRESENT IN CORN, WINE, VINEGAR (FROM GRAPE OR OTHER SOURCES), HONEY, COCOA, BUTTER, AND ROASTED COFFEEIDENTIFIED 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). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Ongoing Test Status | 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] |
| Soil Adsorption/Mobility | 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. |
| Natural Pollution Sources | Based on cell free suspensions of several acetic acid bacteria, 2,3-butanediol is expected to oxidize to acetoin(1). |
| Human Toxicity Excerpts | /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. |
| Artificial Pollution Sources | 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. |
| Environmental Biodegradation | 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/Lacetoin 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). |
| Environmental Bioconcentration | 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). |
| Volatilization from Water/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). |
| Non-Human Toxicity Excerpts | /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. |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2621 |
| Zollcode | 29144090 |
| RTECS-Nr. | EL8790000 |
| R-Sätze (R) | 10-36/38-38-11 |
| Toxizität | skn-rbt 500 mg/24H MOD CNREA8 33,3069,73 |
| Gefahrensymbole | Xi,F |
| Sicherheitshinweise (S) | 26-36-36/37 |
| Gefahrenklasse | 3Eye Irrit. 2Flam. Sol. 2Skin Irrit. 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 4.1B - Flammable solid hazardous materials |
| Gefahrstoffdaten | 513-86-0(Hazardous Substances Data) |
Anwendungen & Verwendung
Occurrence
Reported found in fresh apple, butter, cheddar cheese, coffee, cocoa, honey, wheat bread and wine
Verwenden
Acetoin is a produced via fermentation of wines, dairy products and sugars by fermentive bacteria. Acetoin is used in food flavoring and fragrances and is also found in some fruits and vegetables.