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Dehydracetsäure

Dehydroacetic acid

HCID 122903
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
16807-48-0
Standard-SMILES
CC(=O)C1C(=O)C=C(C)OC1=O
InChIKey
PGRHXDWITVMQBC-UHFFFAOYSA-N
Summenformel
C8H8O4
Durchschnittliche Molmasse
168,15 g/mol
Monoisotopische Masse
168,04225873

Überblick

Dehydroacetic 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.

Namen und Bezeichner

Bevorzugter Name
Dehydroacetic acid
IUPAC
3-acetyl-6-methylpyran-2,4-dione
Lokaler Name
Dehydracetsäure
Englischer Name
Dehydroacetic acid
Summenformel
C8H8O4
Molmasse
168.15

Namen und Synonyme

DEHYDROACETIC ACID520-45-63-Acetyl-6-methyl-2H-pyran-2,4(3H)-dione2H-Pyran-2,4(3H)-dione, 3-acetyl-6-methyl-Acetic acid, dehydro-3-acetyl-6-methylpyran-2,4-dione3-Acetyl-6-methyl-2,4-pyrandione16807-48-03-Acetyl-6-methyl-pyran-2,4-dioneMFCD00066709DTXSID60200143-Acetyl-6-methylpyrandione-2,4
Weitere Namen anzeigen
DHAdhaa2H-Pyran-2-one, 3-acetyl-4-hydroxy-6-methyl-Geogard(R) 221DEHYDRANONEBiocide 470FGeogard(R) 361Geogard(R) 111ADA,Dehydroacetic
3-acetyl-6-methyl-3,4-dihydro-2H-pyran-2,4-dioneCHEBI:137426NSC-87702-Acetyl-5-hydroxy-3-oxo-4-hexenoic acid, .delta.-lactone3-acetyl-6-methyl-2,4-dioxo-3H-pyranDehydroacetic acid [ISO]GlyTouCan:G82156FZEpitope ID:613424

Datenbank-Bezeichner

CAS
16807-48-0、520-45-6

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,3
Polarare Oberfläche (TPSA)
60,4 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
1
Schwere Atome
12
Formalladung
0
Komplexität
287

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Organic Acids
Cosmetics · 2 Einträge

Cosmetic ingredients (Dehydroacetic Acid) -> CIR (Cosmetic Ingredient Review)

Preservative

Odor · 2 Einträge

ODORLESS

Odorless

TasteTASTELESS
Food AdditivesANTIMICROBIAL AGENT -> FDA Substance added to food
Color/Form · 4 Einträge

NEEDLES FROM WATER, RHOMBIC NEEDLES OR PRISMS FROM ALCOHOL

WHITE TO CREAM CRYSTALLINE POWDER

COLORLESS POWDER

Colorless crystals

Solubility · 3 Einträge

(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

Flash Point

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

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)

Gefahrenhinweise

Regulatory Information · 5 Einträge

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

Other Safety Information · 2 Einträge

IMAP assessments - Dehydroacetic acid preservatives: Environment tier II assessment

IMAP assessments - Dehydroacetic acid and its sodium salt: Human health tier II assessment

Fire PotentialSLIGHT
Hazards SummaryMonkeys had seizures in feeding studies (TDLo =3300 mg/kg/18D-I); [RTECS] Rats fed 0.3 gm/kg over 34 days had weight loss; No ill effects in rats fed 0.1 gm/kg for over 2 years; [HSDB] An irritant; [MSDSonline]
FDA Requirements · 2 Einträge

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

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...

Verwendung und Herstellung

Uses · 6 Einträge

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

U.S. Production2023: 29,564 lb
Consumer UsesPreservative
Industry UsesIntermediate
Methods of Manufacturing · 2 Einträge

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.

Formulations/PreparationsGRADES: TECHNICAL, FCC.
Use Classification · 3 Einträge

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

Zugehörige Reaktionen

9
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 464762
HRID 464762als Eduktuspto-grants-1985_10
Reaktionsgleichung von HRID 464763
HRID 464763als Eduktuspto-grants-1985_10
Reaktionsgleichung von HRID 628816
HRID 628816als Eduktuspto-grants-2016_04
Reaktionsgleichung von HRID 1165748
HRID 1165748als Eduktuspto-grants-1990_03
Reaktionsgleichung von HRID 1165749
HRID 1165749als Produktuspto-grants-1990_03
Reaktionsgleichung von HRID 1165750
HRID 1165750als Eduktuspto-grants-1990_03
Reaktionsgleichung von HRID 1870951
HRID 1870951als Eduktuspto-grants-2000_08
Reaktionsgleichung von HRID 2166246
HRID 2166246als Eduktuspto-grants-1990_07
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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
PubChem CID
122903
DTXSID
DTXSID6020014
ChEMBL
CHEMBL284127
ChEBI
CHEBI:137426
EC Number
208-293-9
Nikkaji
J5.151I
157 °C; 315 °F (OPEN CUP)
Boiling Point269.9 °C @ 760 MM HG
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
Melting Point109-111 °C (SUBLIMES)
Vapor Density5.8 (AIR= 1)

Physikochemische Eigenschaften

Schmelzpunkt
111 · 111-113 °C (lit.)
Siedepunkt
270 °C · 270 °C (lit.)
Dichte
1.1816 · 1.1816 (rough estimate)
Dampfdruck
0.001 hPa · 0.001 hPa (20 °C)
Brechungsindex
1.4611 · 1.4611 (estimate)
Flammpunkt
157 °C · 157°C
storage temp.
30 °C · Store below +30°C.
Löslichkeit
2 g/l · 2g/l
Aggregatzustand
Fine Crystalline Powder
pka
5.53 · 5.53±0.40(Predicted)
Farbe
Light yellow or cream
PH
4 · 4 (2g/l, H2O, 20℃)
Geruch (Odor)
almost odorless. slightly bitter-sweet taste.
Wasserlöslichkeit
500 mg/L · 500mg/L at 25℃
Merck
14 · 14,2865
BRN
6129 · 6129
Henry's Law Constant
2.9 · 2.9×101 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität
Stable. Incompatible with oxidizing agents, bases, reducing agents.
Kosmetik-Inhaltsstoffe Funktionen
PRESERVATIVE
InChI
1S/C8H8O4/c1-4-3-6(10)7(5(2)9)8(11)12-4/h3,7H,1-2H3
InChIKey
PGRHXDWITVMQBC-UHFFFAOYSA-N
SMILES
CC(=O)C1C(=O)OC(C)=CC1=O
LogP
0.78 at · 0.78 at 20℃
CAS Datenbank
520 · 520-45-6(CAS DataBase Reference)
NIST chemische Informationen
Dehydroacetic Acid(520-45-6)
EPA chemische Informationen
3 · 3-Acetyl-6-methyl-2H-pyran-2,4(3H)-dione (520-45-6)

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.

EPA Safer ChemicalChemical: Dehydroacetic acid
NFPA Hazard Classification · 3 Einträge

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.

Hazard Classes and Categories · 5 Einträge

Acute Tox. 4 (100%)

Acute toxicity - category 4

Acute toxicity - category 4

Acute toxicity (Oral) - Category 4

Acute Tox. 4 *

Skin, Eye, and Respiratory IrritationsNo primary or allergic skin reactions
Hazardous Reactivities and IncompatibilitiesHIGHLY REACTIVE

Sicherheit und Schutzausrüstung

Fire Fighting ProceduresWATER OR FOAM MAY CAUSE FROTHING.
Disposal Methods · 1 Eintrag

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.

Toxikologische Informationen

Environmental Fate · 3 Einträge

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).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Soil Adsorption/Mobility · 1 Eintrag

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).

TSCA Test Submissions · 1 Eintrag

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.

Natural Pollution SourcesDehydroacetic acid is of anthropogenic origin, and is not known to be produced by natural sources. (SRC)
Human Toxicity Excerpts · 2 Einträge

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.

Artificial Pollution Sources · 1 Eintrag

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).

Environmental Biodegradation · 1 Eintrag

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).

Environmental Bioconcentration · 1 Eintrag

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).

Volatilization from Water/Soil · 1 Eintrag

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).

Non-Human Toxicity Excerpts · 3 Einträge

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/

Regulatorische Informationen

FDA Requirements · 2 Einträge

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.

Sicherheitsdaten

wgk
1
tsca
TSCA listed
hs_code
29322980
RTECS-Nr.
UP8050000
risk_code
22
Toxizität
LD50 orally in rats: 1000 mg/kg (Spencer)
hazard_code
Xn
safety_code
22-26
Speicherklasse
13 - Non Combustible Solids
Giftige Stoffe Daten
520-45-6(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 4 Oral
Selbstentzündungstemperatur
336 °C
General Manufacturing Information · 3 Einträge

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.

Anwendungen

VerwendenDehydroacetic 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

Darstellung

synthetische1) 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).

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Ethylacetoacetat4-Methylen-2-oxetanonFatty acid ethyl esterPolymerization inhibitorToluolSodium hydroxide-ethanol solutionle, Menhaden-N,N-DiethylethanaminNatriumethanolatBenzolHydrogenchloridNatriumhydroxid1,4-Diazabicyclo(2.2.2)octan2-Amino-5-phenyl-4(5H)-oxazolon4H-1,3-Oxazin-4-one, 2,3-dihydro-6-methyl-2-thioxo-

Nachgelagerte Produkte

Dehydracetsäure, Natrium-SalzClopidol4-Hydroxy-6-methylpyran-4-on2,6-Dimethyl-4-pyron

Anbieter4 Anbieter

上海瀚香生物科技有限公司17754423994 · [email protected]
XIAMEN AMITY INDUSTRY AND TRADE CO., LTD.+8618950047208 · [email protected]
Hefei TNJ Chemical Industry Co.,Ltd.+86-0551-65418671 +86-189 4982 3763 · [email protected]
湖北清北云研医药科技有限责任公司18162595016; 18162595016 · [email protected]