dehydroacetic acid (enol form)
3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one enol form
Identification
| Name | dehydroacetic acid (enol form) |
| IUPAC | 3-acetyl-2-hydroxy-6-methylpyran-4-one |
| CAS Number | 771-03-9 |
| EINECS | 212-227-4 |
| FDA UNII | Search |
| Molecular Formula | C8 H8 O4 |
| Molecular Weight | 168.14856000 |
Regulatory
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 |
Organoleptic Properties
| Odor Strength | none |
| Odor Description | at 100.00 %. |
| Taste Description | tasteless |
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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. |
No supplier data available
Potential Uses
Natural Occurrence
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
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.