ChemicalBook CAS DataBase List 520-45-6

520-45-6

Name	Dehydroacetic acid
CAS	520-45-6
EINECS(EC#)	212-227-4
Molecular Formula	C8H8O4
MDL Number	MFCD00066709
Molecular Weight	168.15
MOL File	520-45-6.mol

Synonyms

2-ACETYL-5-HYDROXY-3-OXO-4-HEXENOIC ACID DELTA-LACTONE 2-ACETYL-5-HYDROXY-3-OXO-4-HEXENOIC ACID D-LACTONE 2-ACETYL-5-HYDROXY-3-OXO-4-HEXENOIC ACID GAMMA-LACTONE 3-ACETYL-3,4-DIHYDRO-6-METHYL-2H-PYRAN-2,4-DIONE 3-ACETYL-4-HYDROXY-6-METHYL-2H-PYRAN-2-ONE 3-ACETYL-4-HYDROXY-6-METHYL-2-PYRONE 3-ACETYL-6-METHYL-2H-PYRAN-2,4(3H)-DIONE 3-ACETYL-6-METHYL-2H-PYRONE-2,4-(3H)-DIONE DEHYDRACETIC ACID DEHYDRANONE DEHYDROACETIC ACID DHA LABOTEST-BB LT00053173 2-acetyl-5-hydroxy-3-oxo-4-hexenoicacidelta-lactone 2-Acetyl-5-hydroxy-3-oxo-4-hexenoicacid-lactone 2H-Pyran-2,4(3H)-dione, 3-acetyl-6-methyl- 2H-Pyran-2-one, 3-acetyl-4-hydroxy-6-methyl- 3-acetyl-4-hydroxy-6-methyl-2h-pyran-2-on 3-Acetyl-4-hydroxy-6-methyl-2-pyrone cyclic ketone 3-Acetyl-6-methyl-2,3-dihydropyran-2,4-dione

Chemical Properties

Appearance	white to light yellow crystal powder
Melting point	111-113 °C (lit.)
Boiling point	270 °C (lit.)
bulk density	700kg/m3
density	1.1816 (rough estimate)
vapor pressure	0.001 hPa (20 °C)
refractive index	1.4611 (estimate)
Fp	157°C
storage temp.	0-6°C
solubility	2g/l
form	Fine Crystalline Powder
pka	5.53±0.40(Predicted)
color	Light yellow or cream
Odor	almost odorless. slightly bitter-sweet taste.
PH	4 (2g/l, H2O, 20℃)
Stability:	Stable. Incompatible with oxidizing agents, bases, reducing agents.
Water Solubility	500mg/L at 25℃
Usage	Geogard(R) 221 preservative is based on dehydroacetic acid (DHA) and benzyl alcohol, and therefore is recognized by major cosmetic, toiletry and fragrance regulatory authorities worldwide for use in cosmetic and personal care products.
Detection Methods	HPLC,NMR
Merck	14,2865
BRN	6129
Henry's Law Constant	2.9×10¹ mol/(m³Pa) at 25℃, HSDB (2015)
Cosmetics Ingredients Functions	PRESERVATIVE
Cosmetic Ingredient Review (CIR)	Dehydroacetic acid (520-45-6)
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 20℃
Uses	Dehydroacetic Acid (DHA) is a preservative that is a crystalline powder with a solubility of less than 0.1 g in 100 g of water at 25°C. It can undergo a variety of chemical reactions which give it utility in many applications. It is used at 0.01–0.5% for microbiological growth inhibition in various foods. It is used for cut or peeled squash, with no more than 65 ppm remaining in or on the prepared squash. less more
CAS DataBase Reference	520-45-6(CAS DataBase Reference)
NIST Chemistry Reference	Dehydroacetic Acid(520-45-6)
EPA Substance Registry System	520-45-6(EPA Substance)

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264-P270-P301+P312-P501
Hazard Codes	Xn
Risk Statements	R22:Harmful if swallowed. less more
Safety Statements	S22:Do not breathe dust . less more
WGK Germany	1
RTECS	UP8050000
Autoignition Temperature	336 °C
TSCA	Yes
REACH Registrations	Active
HS Code	29322980
Storage Class	13 - Non Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral
Safety Profile	Poison by ingestion. Moderately toxic by intraperitoneal route. Questionable carcinogen with experimental tumorigenic data. Combustible when exposed to heat or flame. When heated to decomposition it emits acrid smoke and irritating fumes. less more
Hazardous Substances Data	520-45-6(Hazardous Substances Data)
Toxicity	LD50 orally in rats: 1000 mg/kg (Spencer) less more

Raw materials And Preparation Products

Hazard Information

Description

Dehydroacetic acid is an obsolete fungicide. It is highly soluble in water and is also a volatile substance. Ecotoxicological data is scarce. Dehydroacetic acid is moderately toxic to mammals via the oral route, is a neurotoxin and irritant.

Chemical Properties

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.

Definition

ChEBI: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.

Preparation

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).

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 5105, 1984 DOI: 10.1021/jo00200a018

General Description

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.

Flammability and Explosibility

Notclassified

Solubility in organics

soluble in most hydrocarbons, but only about 3% soluble in alcohol and about 1.5% in Propylene glycol. Being an acid, it is soluble in aqueous alkali under formation of alkali salt .

storage

Store at -20°C

Pesticide Type

Fungicide

Material Safety Data Sheet(MSDS)

Spectrum Detail

Well-known Reagent Company Product Information

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