dehydroacetic acid (enol form)
3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one enol form
 
Notes:
None found
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CAS Number: 771-03-9Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 212-227-4
XlogP3-AA: 1.00 (est)
Molecular Weight: 168.14856000
Formula: C8 H8 O4
BioActivity Summary: listing
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Category: preservatives
 
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Physical Properties:
Appearance: colorless powder (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 352.00 to  353.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 0.000002 mmHg @ 25.00 °C. (est)
Flash Point: 300.00 °F. TCC ( 149.20 °C. ) (est)
logP (o/w): 0.221 (est)
Soluble in:
 alcohol
 water, 8.178e+005 mg/L @ 25 °C (est)
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Organoleptic Properties:
Odor Strength: none
 
Odor Description:
at 100.00 %. 
odorless
Taste Description:
tasteless
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: preservatives
Recommendation for dehydroacetic acid (enol form) usage levels up to:
 not for fragrance use.
 
Recommendation for dehydroacetic acid (enol form) flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
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EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 10623
National Institute of Allergy and Infectious Diseases: Data
 3-acetyl-2-hydroxy-6-methylpyran-4-one
Chemidplus: 0000771039
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References:
 3-acetyl-2-hydroxy-6-methylpyran-4-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 10623
Pubchem (sid): 135206421
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS): View
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VCF-Online: VCF Volatile Compounds in Food
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 found in nature
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Synonyms:
3-acetyl-2-hydroxy-6-methylpyran-4-one (enol form)
3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one enol form
 dehydroacetic acid enol form
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Articles:
PubMed: Synthesis and preclinical pharmacokinetic study of DHA-10, a novel potential antifungal pogostone analogue.
PubMed: Dehydroacetic Acid Derivatives Bearing Amide or Urea Moieties as Effective Anion Receptors.
PubMed: Analogues of Dehydroacetic Acid as Selective and Potent Agonists of an Ectopic Odorant Receptor through a Combination of Hydrophilic and Hydrophobic Interactions.
PubMed: Simultaneous determination of nine preservatives in food by liquid chromatography with the aid of coagulant in the clean-up process.
PubMed: Prevention of Dietary-Fat-Fueled Ketogenesis Attenuates BRAF V600E Tumor Growth.
PubMed: Allergic contact dermatitis caused by resorcinol and sodium dehydroacetate in a patient with leg ulcers.
PubMed: Formation and Transformation Behavior of Sodium Dehydroacetate Hydrates.
PubMed: Physicochemical Properties and Storage Stability of Microencapsulated DHA-Rich Oil with Different Wall Materials.
PubMed: Effects of preservatives on Alicyclobacillus acidoterrestris growth and guaiacol production.
PubMed: Vibrational spectroscopic study of dehydroacetic acid and its cinnamoyl pyrone derivatives.
PubMed: Aspergillus oryzae CsyB catalyzes the condensation of two β-ketoacyl-CoAs to form 3-acetyl-4-hydroxy-6-alkyl-α-pyrone.
PubMed: [Identification of benzoic acid, sorbic aicid and dehydroacetic acid residues in alcoholic drinks and beverages].
PubMed: [Analysis of the reaction solution for dehydroacetic acid by ethyl acetoacetate using high formance liquid chromatography].
PubMed: [Simultaneous determination of twelve sweeteners and nine preservatives in foods by solid-phase extraction and LC-MS/MS].
PubMed: Absolute quantification of dehydroacetic acid in processed foods using quantitative ¹H NMR.
PubMed: Spectral and thermal characterization of 3-acetyl-5-azophenyl-4-hydroxy-6-methyl-pyran-2-one and its metal complexes.
PubMed: Bidentate coordinating behaviour of chalcone based ligands towards oxocations: VO(IV) and Mo(V).
PubMed: Analysis of nine food additives in red wine by ion-suppression reversed-phase high-performance liquid chromatography using trifluoroacetic acid and ammonium acetate as ion-suppressors.
PubMed: Application of dispersive solid-phase extraction and ultra-fast liquid chromatography-tandem quadrupole mass spectrometry in food additive residue analysis of red wine.
PubMed: Sodium dehydroacetate: an emerging allergen.
PubMed: Simultaneous determination of eleven preservatives in cosmetics by micellar electrokinetic chromatography.
PubMed: Large volume sample stacking with EOF and sweeping in CE for determination of common preservatives in cosmetic products by chemometric experimental design.
PubMed: Determination and depletion of dehydroacetic acid residue in chicken tissues.
PubMed: [Influences of ion-suppressors on retention behaviors of nine food additives in reversed-phase high performance liquid chromatographic separation].
PubMed: Allergic contact dermatitis caused by sodium dehydroacetate, not hyaluronic acid, in Ialuset® cream.
PubMed: A novel and convenient synthesis of 4-hydroxy-6-methyl-3-(1-(phenylimino) ethyl)-2H-pyran-2-one derivatives under ultrasound irradiation.
PubMed: Synthesis of disubstituted 1,4-diazepines with affinity to GABAA-receptor subtypes.
PubMed: Effect of extracted housefly pupae peptide mixture on chilled pork preservation.
PubMed: Synthesis and structural characterization of a fused bispyrone and preparation of the first metal bispyrylium complexes.
PubMed: Active packaging for topical cosmetic/drug products: a hot-melt extruded preservative delivery device.
PubMed: Mononuclear ruthenium(III) complexes containing chelating thiosemicarbazones: synthesis, characterization and catalytic property.
PubMed: [Analysis of preservatives used in cosmetic products: salicylic acid, sodium benzoate, sodium dehydroacetate, potassium sorbate, phenoxyethanol, and parabens].
PubMed: Synthesis and phytotoxic activity of new pyridones derived from 4-hydroxy-6-methylpyridin-2(1H)-one.
PubMed: Evaluation of the efficacy of four weak acids as antifungal preservatives in low-acid intermediate moisture model food systems.
PubMed: Antibacterial interactions of monolaurin with commonly used antimicrobials and food components.
PubMed: [A convenient synthesis of furans using bromacetyl-pyran-2-one].
PubMed: Preparation of achiral and chiral (E)-enaminopyran-2,4-diones and their phytotoxic activity.
PubMed: [Compound preservative and cyclamat determinated by gas chromatography].
PubMed: [Method study on dehydroaetic acid in food by high performance liquid chromatography].
PubMed: Anticoagulant effect of sodium dehydroacetate (DHA-S) in rats.
PubMed: [Simultaneous determination of nine kinds of preservatives in foods by HPLC].
PubMed: [Determination of dehydroacetic acid and its sodium salt in food products and polymeric packing materials].
PubMed: Kinetics of the substitution of dehydroacetic acid in tris (dehydroacetato) Fe(III) complex by 8-hydroxyquinoline, di- and tetra-hydroxyquinone.
PubMed: 1H and 13C NMR identification of unexpected 3,4-dihydroquinoxalines in the syntheses of 1,5-benzodiazepine derivatives.
PubMed: Efficacy and tolerability of a combination of Lyprinol and high concentrations of EPA and DHA in inflammatory rheumatoid disorders.
PubMed: Optimization by experimental design and artificial neural networks of the ion-interaction reversed-phase liquid chromatographic separation of twenty cosmetic preservatives.
PubMed: [A study on the contents of fat and fatty acids in five shellfishes].
PubMed: Simultaneous analysis of dehydroacetic acid, benzoic acid, sorbic acid and salicylic acid in cosmetic products by solid-phase extraction and high-performance liquid chromatography.
PubMed: Estimation of preservative concentrations in foods and their daily intake based on official inspection results in Japan in fiscal year 1998.
PubMed: Power Doppler enhancement of the placenta by dehydroepiandrosterone sulphate in term pregnancy.
PubMed: Investigation of a pulsed-laser thermo-optical absorbance detector for the determination of food preservatives separated by capillary electrophoresis.
PubMed: Relative androgenicity, blood pressure levels, and cardiovascular risk factors in young healthy women.
PubMed: Micellar electrokinetic capillary chromatographic determination of artificial sweeteners in low-Joule soft drinks and other foods.
PubMed: Controlled release of dehydroacetic acid sodium salt for the stability improvement of cosmetic formulations*.
PubMed: The role of the endocrine factors and obesity in hormone-dependent gynecological neoplasias.
PubMed: Synthesis and inotropic activity of pyrazolo[4,3-c]pyridine-4-ones and related compounds.
PubMed: [The significance of measurement of serum type IV 7S collagen on administration of DHA-S].
PubMed: Effects of cytotoxic chemotherapy on ovarian and adrenal steroidogenesis in pre-menopausal breast cancer patients.
PubMed: [Influence of various steroid hormones on prostaglandin E2 metabolism in the smooth muscles of the human uterus--special reference to isolation and activity of 15 hydroxy prostaglandin dehydrogenase and 9 keto reductase].
PubMed: The biochemistry of cyst fluids.
PubMed: Qualitative and quantitative determination of Prevan in cosmetic emulsions by direct analysis via fast atom bombardment/collisional spectroscopy.
PubMed: Simultaneous determination of the nine food additives using high-performance liquid chromatography.
PubMed: Micronucleus tests in mice on 39 food additives and eight miscellaneous chemicals.
PubMed: Dehydroacetic acid sodium salt stability in cosmetic preservative mixtures.
PubMed: [Studies on the teratogenic potential of sodium dehydroacetate in rats].
PubMed: Molecular dynamics simulations of "loop closing" in the enzyme triose phosphate isomerase.
PubMed: Mould growth and aflatoxin accumulation in the presence of newly synthetized analogues of dehydroacetic acid.
PubMed: [Biosynthesis of prostaglandin in human cervical tissue].
PubMed: The use of nonradiolabelled steroid infusions to investigate the origin of oestrone sulphate in postmenopausal women.
PubMed: [Experimental study of the possible use of sodium dehydroacetate as a food additive].
PubMed: Simultaneous gas chromatographic determination of carboxylic acids in soft drinks and jams.
PubMed: Liquid chromatographic analysis of dehydroacetic acid and its application to wines.
PubMed: Differentiation of male hypogonadotropic hypogonadism and constitutional delay of puberty by pulsatile administration of gonadotropin-releasing hormone.
PubMed: [Studies on the acute oral toxicity of dehydroacetic acid, sorbic acid and their combination compound in rats].
PubMed: Gas-liquid chromatographic determination of dehydroacetic acid in squash and wine.
PubMed: [Case of anaphylactic shock presumably caused by a barium preparation].
PubMed: Synthesis of δ-lactonic pheromones ofXylocopa hirsutissima andVespa orientalis and an allomone of some ants of genusCamponotus.
PubMed: A series of inhibitors of azo dye hepatocarcinogenesis partially reverse the azo dye-induced decrease in liver RNA/DNA ratio.
PubMed: Thermodynamic parameters of molecular complexes in aqueous solution: enthalpy-entropy compensation in a series of complexes of caffeine with beta- naphthoxyacetic acid and drug-related aromatic compounds.
PubMed: Effects of some drugs on ripening of uterine cervix in nonpregnant castrated and pregnant rats.
PubMed: Exogenous DHA-S half-life: a good index of intrauterine growth retardation.
PubMed: [(Hydroxyphenyl)ethanones from dehydroacetic acid (author's transl)].
PubMed: Dehydroacetic acid as a reagent for the separation and gravimetric determination of copper(II), aluminium and beryllium.
PubMed: [Fluorescence of borate complexes. 3. Fluorometric determination of dehydroacetic acid (DHA) in foods].
PubMed: [Fluorometric determination of dehydroacetic acid and its sodium salt with boric acid in acetic anhydride].
PubMed: Kinetics of reaction of dehydroacetic acid. II. Reaction with primary amines.
PubMed: Inhibitory effect of dehydroacetic acid on induction of hepatoma in rats fed 4-(dimethylamino) azobenzene.
PubMed: [Studies on ketene and its derivatives. XXV. Ring-closure of 3-acetyl-4-hydroxy-6-methyl-1H-2-pyridone oxime and dehydroacetic acid oxime].
PubMed: [The spectrophotometric determination of anions by solvent extraction with metal chelate cations. XXVII. A new colorimetric method for the determination of dehydroacetic acid].
PubMed: Kinetics of reaction of dehydroacetic acid. I. Reaction with primary amines. I.
PubMed: [ON THE TOLERANCE OF DEHYDROACETIC ACID].
PubMed: [ON THE DECOMPOSITION OF DEHYDROACETIC ACID WITH OXIDIZING AGENTS].
PubMed: On the reaction products from dehydroacetic acid and amino acids.
PubMed: On the reaction of dehydroacetic acid to hydroxylamine.
PubMed: [ON THE PKA VALUE OF 3-ACETYL-4-HYDROXYCOUMARIN AND DEHYDROACETIC ACID].
PubMed: THE METABOLISM OF DEHYDROACETIC ACID (DHA).
PubMed: STUDIES ON PYRONE DERIVATIVES. XI. DIMORPHISM OF DEHYDROACETIC ACID.
PubMed: [Inhibitory action of sodium dehydroacetate and 3-butyryl-4-hydroxycoumarin on D-amino acid oxidase].
PubMed: [Interaction of sodium dehydroacetate and 3-butyryl-4-hydroxycoumarin with flavins].
PubMed: [Mode of antibacterial activity of 3-acetyl-4-hydroxycoumarin and dehydroacetic acid. I].
PubMed: Studies on pyrone derivatives. VII. On the syntheses of dehydroacetic acid analogue having aroyl group in its side chain.
PubMed: [Studies on pyrone derivatives. VII. Iron chelates of dehydroacetic acid].
PubMed: The studies on the fluid environment of ascaris: influence of pH and effect of antibiotics and antimycotics (dehydroacetic acid) in fluid media upon the survival length and the duration of normal locomotion.
PubMed: Use of a sodium dehydroacetate-sodium oxalate dentifrice in the control of dental caries.
PubMed: Potentiation of smooth surface caries by sodium dehydroacetate variously administered to the white rat.
PubMed: Effect of fluoride, iodoacetic acid, penicillin, sodium lauroyl sarcosinate and dehydroacetic acid on certain oral bacteria of white rats fed a smooth surface caries diet: preliminary report.
PubMed: Effect of sodium lauroyl sarcosinate and dehydroacetic acid on sulcal and smooth surface caries (buccal-lingual) in the white rat.
PubMed: The effect of sodium N-lauroyl sarcosinate and of sodium dehydroacetate on the enzymes of the gastrointestinal tract.
PubMed: Dehydroacetic acid: its enhancement of penicillemia in man.
PubMed: In vitro antimicrobial activity of a dehydroacetic acid and p-chlor-m-xylenol combination.
PubMed: [The preservation of food with dehydroacetic acid].
PubMed: Dehydroacetic acid (DHA). Detoxication and effects on renal function.
PubMed: Dehydroacetic acid (DHA). Estimation, absorption and distribution.
PubMed: Dehydroacetic acid (DHA). General pharmacology and mechanism of action.
PubMed: Dehydroacetic acid (DHA). Acute and chronic toxicity.
PubMed: A preliminary report on the antimicrobic properties of dehydroacetic acid.
PubMed: Antibacterial properties of compounds having tricarbonylmethane group in their structure; antibacterial properties of 1,1-dimethyl-4-acylcylohexanediones-3,5,dehydroacetic acid and 3-acyl-4-hydroxycoumarins.
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