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다이하이드로아세트 산

Dehydroacetic acid

HCID 122903
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
16807-48-0
표준 SMILES
CC(=O)C1C(=O)C=C(C)OC1=O
InChIKey
PGRHXDWITVMQBC-UHFFFAOYSA-N
분자식
C8H8O4
평균 분자량
168.15 g/mol
단동위원소 질량
168.04225873

개요

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.

이름 및 식별자

우선 이름
Dehydroacetic acid
IUPAC
3-acetyl-6-methylpyran-2,4-dione
현지명
다이하이드로아세트 산
영어명
Dehydroacetic acid
분자식
C8H8O4
분자량
168.15

이름 및 동의어

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
이름 더 보기
다이하이드로아세트산다이하이드로아세트산DHAdhaa2H-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

데이터베이스 식별자

CAS
16807-48-0、520-45-6

물성

구조 계산 물성

XLogP
0.3
극성 표면적
60.4 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
4
회전 가능 결합 수
1
무거운 원자 수
12
형식 전하
0
복잡도
287

실험 및 물리화학적 성질

Chemical ClassesOther Classes -> Organic Acids
Cosmetics · 2건

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

Preservative

Odor · 2건

ODORLESS

Odorless

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

NEEDLES FROM WATER, RHOMBIC NEEDLES OR PRISMS FROM ALCOHOL

WHITE TO CREAM CRYSTALLINE POWDER

COLORLESS POWDER

Colorless crystals

Solubility · 3건

(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 Point157 °C; 315 °F (OPEN CUP)
Boiling Point269.9 °C @ 760 MM HG

안전 및 규제

GHS 분류

GHS Classification · 6건

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)

유해성 정보

Regulatory Information · 5건

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 · 2건

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 · 2건

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.

화학 및 산업

약리 정보

Metabolism/Metabolites · 2건

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...

용도 및 제조

Uses · 6건

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 · 2건

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 · 3건

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

General Manufacturing Information · 3건

관련 반응

9건
반응 기록 만들기
HRID 464762 반응식
HRID 464762반응물로uspto-grants-1985_10
HRID 464763 반응식
HRID 464763반응물로uspto-grants-1985_10
HRID 628816 반응식
HRID 628816반응물로uspto-grants-2016_04
HRID 1165748 반응식
HRID 1165748반응물로uspto-grants-1990_03
HRID 1165749 반응식
HRID 1165749생성물로uspto-grants-1990_03
HRID 1165750 반응식
HRID 1165750반응물로uspto-grants-1990_03
HRID 1870951 반응식
HRID 1870951반응물로uspto-grants-2000_08
HRID 2166246 반응식
HRID 2166246반응물로uspto-grants-1990_07
1 / 2 페이지

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
PubChem CID
122903
DTXSID
DTXSID6020014
ChEMBL
CHEMBL284127
ChEBI
CHEBI:137426
EC Number
208-293-9
Nikkaji
J5.151I
Decomposition
When heated to decomposition it emits acrid smoke and irritating fumes.
Melting Point109-111 °C (SUBLIMES)
Vapor Density5.8 (AIR= 1)

물리화학적 성질

녹는점
111 · 111-113 °C (lit.)
끓는 점
270 °C · 270 °C (lit.)
밀도
1.1816 · 1.1816 (rough estimate)
증기압
0.001 hPa · 0.001 hPa (20 °C)
굴절률
1.4611 · 1.4611 (estimate)
인화점
157 °C · 157°C
저장 조건
30 °C · Store below +30°C.
용해도
2 g/L · 2g/L
물리적 상태
미세 결정성 분말
산도 계수 (pKa)
5.53 · 5.53±0.40(Predicted)
색상
연한 노란색 또는 크림색
수소이온지수(pH)
4 · 4 (2g/l, H2O, 20℃)
냄새
almost odorless. slightly bitter-sweet taste.
수용성
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)
안정성
안정적인. 산화제, 염기, 환원제와 호환되지 않습니다.
화장품 원료 기능
항균 방부제
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℃
NIST
Dehydroacetic Acid(520-45-6)
EPA
3 · 3-Acetyl-6-methyl-2H-pyran-2,4(3H)-dione (520-45-6)
화학적 성질 · 1건

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.

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

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 · 5건

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

안전 및 보호

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

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.

독성 정보

Environmental Fate · 3건

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 · 1건

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 · 1건

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 · 2건

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 · 1건

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 · 1건

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 · 1건

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 · 1건

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 · 3건

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/

규제 정보

FDA Requirements · 2건

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.

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
UP8050000
독성
LD50 orally in rats: 1000 mg/kg (Spencer)
HS 번호
29322980
risk_code
22
hazard_code
Xn
safety_code
22-26
기존화학 물질
KE-00123
자연 발화 온도
336 °C
Hazard Classifications
Acute Tox. 4 Oral
스토리지 클래스
13 - Non Combustible Solids
유해 물질 데이터
520-45-6(Hazardous Substances Data)

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.

응용 분야 · 2건

용도Dehydroacetic 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

일반 설명Dehydroacetic 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.

제조 방법

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).

상·하류 제품 정보

상류 원료

아세트초산에틸아세틸 케텐Fatty acid ethyl esterPolymerization inhibitor톨루엔Sodium hydroxide-ethanol solution멘헤이든오일트리에틸아민나트륨 에톡시드벤젠염산수산화나트륨트리에틸렌디아민퍼몰린4H-1,3-Oxazin-4-one, 2,3-dihydro-6-methyl-2-thioxo-

하류 제품

디하이드로초산나트륨클로피돌4-히드록시-6-메틸-2-피론2,6-디메틸-4H-피란-4-온

공급사4 곳

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]