16807-48-0CC(=O)C1C(=O)C=C(C)OC1=OPGRHXDWITVMQBC-UHFFFAOYSA-NDehydroacetic acid is a pyran-2,4-dione substituted at position 3 by an acetyl group and at position 6 by a methyl group. A fungicide and bactericide it is used primarily in processed fruit and vegetables. It has a role as a fungicide, an antibacterial agent and a plasticiser. It is a pyran-2,4-dione and a ketone.
Cosmetic ingredients (Dehydroacetic Acid) -> CIR (Cosmetic Ingredient Review)
Preservative
ODORLESS
Odorless
NEEDLES FROM WATER, RHOMBIC NEEDLES OR PRISMS FROM ALCOHOL
WHITE TO CREAM CRYSTALLINE POWDER
COLORLESS POWDER
Colorless crystals
(WT/WT) 22% IN ACETONE, 18% IN BENZENE, 5% IN METHANOL, 3% IN USP ETHANOL, 3% IN CARBON TETRACHLORIDE, 5% IN ETHER, 0.7% IN N-HEPTANE, LESS THAN 0.1% IN GLYCEROL, 1.6% IN OLIVE OIL, 1.7% IN PROPYLENE GLYCOL, LESS THAN 0.1% IN WATER AT 25 °C
SOL IN ALKALIES
water solubility = 690 mg/l @ 25 °C
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Chemical: 2H-Pyran-2,4(3H)-dione, 3-acetyl-6-methyl-
Chemical: 4H-Pyran-4-one, 3-acetyl-2-hydroxy-6-methyl-
2H-Pyran-2,4(3H)-dione, 3-acetyl-6-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2H-Pyran-2,4(3H)-dione, 3-acetyl-6-methyl- 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)
REACH registered substance: 3-acetyl-6-methyl-2H-pyran-2,4(3H)-dione (EC: 208-293-9)
Dehydracetic acid: Does not have an individual approval but may be used under an appropriate group standard
IMAP assessments - Dehydroacetic acid preservatives: Environment tier II assessment
IMAP assessments - Dehydroacetic acid and its sodium salt: Human health tier II assessment
Dehydroacetic acid is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient.
METABOLITES IN RABBIT ARE: TRIACETIC ACID LACTONE, A HYDROXY DHA & POSSIBLY THE SALT OF TRIACETIC ACID LACTONE 3-CARBOXYLIC ACID.
...NATURAL PRODUCT OF ADRENAL STEROID METABOLISM...
CIR ingredient: Dehydroacetic Acid
Used as a plasticizer, bactericide, preservative, and fungicide; Also used in toothpastes and pickles; [HSDB]
Using Disinfectants or Biocides [Category: Clean]
ORGANIC SYNTHESIS; AS PLASTICIZER; BACTERICIDE; FUNGICIDE; IN ANTIENZYME TOOTHPASTES; TO REDUCE PICKLE BLOATING
FUNGICIDE USED IN COSMETICS & ON PROCESSED FRUITS & VEGETABLES
FORMERLY APPLIED AS A DIP OR WRAPPER IMPREGNANT
POLYMERIZATION PRODUCT OF KETENE: STEELE ET AL, J ORG CHEM 14: 460 (1949). FROM ETHYL ACETOACETATE: ARNDT, ORG SYN COLL VOL 3: 231 (1955).
By action of N-bromosuccinamide on ketene dimer; by strong heating of acetoacetic ester.
EPA Safer Chemical Functional Use Classes -> Preservatives and Antioxidants
Safer Chemical Classes -> Yellow triangle - The chemical has met Safer Choice Criteria for its functional ingredient-class, but has some hazard profile issues
Cosmetics -> Preservative
読み込み中…
16807-48-0、520-45-6DTXSID6020014CHEMBL284127CHEBI:137426化学的特性Dehydroacetic acid is a white to cream-coloured powder that is only very slightly soluble in water (less than 0.1 %). However, the sodium salt hydrate (CSH7Na04.H20) has a solubility of 33% in water at 25°C, and 48% in propylene glycol. The acid is 22% soluble in acetone, 18% in benzene, and I g dissolves in about 35 ml of ethanol.It is used to reduce pickle bloating, and as a pesticide and preservative for squash and strawberries. Its permissible use level is 65ppm.Dehydroacetic acid is one of the food additives found in red wine and was determined by ultra-fast liquid chromatography-tandem quadrupole mass spectrometry (UFLC-MS/MS).To assay dehydroacetic acid, add 500 mg to a 250-ml Erlenmeyer flask and dissolve in 75 ml of neutral alcohol. Following the addition of phenolphthalein T.S., titrate with 0.1 N NaOH to a pink end-point that persists for at least 30 s. Each ml of 0.1 N NaOH = 16.82 mg of dehydroacetic acid (National Academy of Sciences, 1963).Dehydroacetic acid is a synthetic chemical (no plant-based preservatives that meet our efficacy standards currently exist) that is considered to be a low hazard for human health and for the environment.
Dehydroacetic acid is an indirect food additive for use as a component of adhesives.
1 - Materials that, under emergency conditions, can cause significant irritation.
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.
Acute Tox. 4 (100%)
Acute toxicity - category 4
Acute toxicity - category 4
Acute toxicity (Oral) - Category 4
Acute Tox. 4 *
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 120(SRC), determined from a measured water solubility of 690 mg/l(2) and a recommended regression-derived equation(3), indicates that dehydroacetic acid is expected to have high mobility in soil(SRC). Volatilization of dehydroacetic acid from moist soil surfaces is not expected to be important(SRC) given an estimated Henry's Law constant of 3.4X10-7 atm-cu m/mole(SRC), determined from its measured water solubility, 690 mg/l(2), and extrapolated vapor pressure, 1.1X10-3 mm Hg(4). Dehydroacetic acid is not expected to volatilize from dry soil surfaces based on its extrapolated vapor pressure(4). Biodegradation of dehydroacetic acid in soil may be important(SRC), based on its biodegradation in standard biodegradability tests(2,5).
AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 120(SRC), a measured water solubility of 690 mg/l(2) and a recommended regression-derived equation(3), indicates that dehydroacetic acid is not expected to adsorb to suspended solids and sediment in water(SRC). Dehydroacetic acid is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 3.4X10-7 atm-cu m/mole(SRC), from its measured water solubility, 690 mg/l(2), and extrapolated vapor pressure, 1.1X10-3 mm Hg(4). According to a classification scheme(5), an estimated BCF value of 15(3,SRC), from a measured water solubility(2), suggests that bioconcentration in aquatic organisms is low(SRC). A biodegradation study on dehydroacetic acid, based on BOD measurements, using an activated sludge seed, and an initial chemical concentration of 100 mg/l indicated 84% biodegradation after 2 weeks(2). Dehydroacetic acid was observed to degrade in six aerobic biodegradation tests (coupled units test, Zahn-Wellens test, MITI test, Sturm CO2 evolution test, OECD screening test, and closed bottle test)(6).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dehydroacetic acid, which has an extrapolated vapor pressure of 1.1X10-3 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dehydroacetic acid 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 about 4.9 hours(3,SRC). The rate constant for the vapor-phase reaction of dehydroacetic acid with ozone has been estimated as 1.1X10-17 cu cm/molecule-sec at 25 °C(3,SRC). This corresponds to an atmospheric half-life of about 1.0 day at an atmospheric ozone concn of 7X10+11 cu cm/molecule-sec at 25 °C(3,SRC).
The Koc of dehydroacetic acid is estimated as approximately 120(SRC), using a measured water solubility of 690 mg/l(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that dehydroacetic acid is expected to have high mobility in soil(SRC).
The mutagenicity of dehydroacetic acid was evaluated in Salmonella tester strains TA98, TA100, TA1535, TA1537 and TA1538 (Ames Test), both in the presence and absence of added metabolic activation by Aroclor-induced rat liver S9 fraction. Based on preliminary toxicity determinations, dehydroacetic acid, diluted in water, was tested at concentrations up to 8mg/plate using the plate incorporation technique. Dehydroacetic acid did not cause a positive response in any tester strain with or without metabolic activation.
CAUSES IMPAIRED KIDNEY FUNCTION. LARGE DOSES CAN CAUSE VOMITING, ATAXIA, CONVULSIONS.
NO PRIMARY OR ALLERGIC SKIN REACTIONS. HUMANS INGESTED 0.01 G/KG DAILY FOR 150 DAYS WITHOUT OBSERVABLE ILL-EFFECTS.
Dehydroacetic acid's production and use in organic syntheses, as a plasticizer, bactericide, in anti-enzyme toothpastes(1), and as a fungicide in cosmetics and on processed fruits and vegetables(2) may result in its release to the environment(SRC).
A biodegradation study on dehydroacetic acid, based on BOD measurements, using an activated sludge seed, and an initial chemical concentration of 100 mg/l indicated 84% biodegradation after 2 weeks(1). Dehydroacetic acid was observed to degrade in six aerobic biodegradation tests (coupled units test, Zahn-Wellens test, MITI test, Sturm CO2 evolution test, OECD screening test, and closed bottle test)(2). 99% DOC removal was observed in the coupled units test using a sewage seed; 96% DOC removal was observed after 6 days using an activated sludge seed in the Zahn-Wellens test; 91% DOC removal was observed after 14 days incubation using an activated sludge seed in the MITI test; 100% DOC removal was observed after 28 days incubation using a sewage seed in the Sturm test; 98% DOC removal was observed after 19 days incubation using a sewage seed in the OECD screening test; and 81% BODT was observed after 28 days using a sewage seed in the closed bottle test(2).
An estimated BCF value of 15 was calculated for dehydroacetic acid(SRC), using a measured water solubility of 690 mg/l(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).
The Henry's Law constant for dehydroacetic acid is estimated as 3.4X10-7 atm-cu m/mole(SRC) from its extrapolated vapor pressure, 1.1X10-3 mm Hg(1), and measured water solubility, 690 mg/l(2). This value indicates that dehydroacetic acid will volatilize very slowly from water surfaces(3,SRC). 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) is estimated as approximately 140 days(3,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 1030 days(3,SRC). Dehydroacetic acid's Henry's Law constant(1,2,SRC) indicates that volatilization from moist soil surfaces is not expected to be important(SRC). Dehydroacetic acid is not expected to volatilize from dry soil surfaces based on an extrapolated vapor pressure of 1.1X10-3 mm Hg(1,SRC).
AT HIGH DOSAGE LEVELS MONKEYS SHOWED ANOREXIA, VOMITING, WEAKNESS, STUPOR, ATAXIA, & CONVULSIONS.
...LOSS OF WEIGHT IN RATS FED WITH 0.3 G/KG OVER 34 DAYS BUT NO ILL-EFFECTS AT 0.1 G/KG FOR OVER 2 YR.
SODIUM DEHYDROACETATE (120-300 MG/KG/DAY FOR 3 OR 7 DAYS IP) GIVEN TO MICE INCR LIPID DROPLETS IN CENTRILOBULAR & MIDLOBULAR HEPATOCYTES. IT PRODUCED LITTLE OR NO PROLIFERATION OF SMOOTH ENDOPLASMIC RETICULUM IN HEPATOCYTES & LITTLE INCR IN DRUG-METAB ENZYME ACTIVITY. /SODIUM DEHYDROACETATE/
Dehydroacetic acid is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient.
Dehydroacetic acid is an indirect food additive for use as a component of adhesives.
All Other Basic Organic Chemical Manufacturing
2H-Pyran-2,4(3H)-dione, 3-acetyl-6-methyl-: ACTIVE
TO INHIBIT MICROBIOLOGICAL GROWTH (0.01-0.5%) IN OR ON PHARMACEUTICALS INCL SEMEN DILUTERS, FOODS, & COSMETICS. ISRAELIS ARE TRYING TO DEVELOP INEXPENSIVE STABLE DERIVATIVE FOR USE IN FEED. ...IT PREVENTS POULTRY DEATH CAUSED BY EXCESSIVE HEAT OR COLD STRESSES.
用途抗真菌薬として皮膚白癬症に用いられる。また食品の防腐剤としても使用される。チーズ、バター、マーガリンに。清涼飲料水、保存水に。ミソまたはアンなどにも。(食品添加物)
用途食品および化粧品などの保存料
使用Dehydroacetic acid (DHS) is used as stabilizer for cosmetic and pharmaceutical products due to its fungicide and bactericide activity, as additive for PVC-stabilizers and for the syntheses of veterinary medicines. Product Data Sheet
一般的な説明Dehydroacetic acid is a pyrone derivative, that is typically synthesized by the base-catalyzed dimerization of diketene. It is used as a preservative in pharmaceutical, food and cosmetic products.Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
製造方法1) Dehydroacetic acid is prepared from Ethyl acetoacetate by self-condensation under mildly alkaline conditions (Sodium bicarbonate). 2) by polymerization of Ketene, obtained by thermal decomposition of Acetone).
定義本品は、次の化学式で表される環状ケトンである。