HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
3-Hydroxy-2-methyl-4-pyron
MALTOL · 3-HYDROXY-2-METHYL-4-PYRONE · LARIXINIC ACID · Veltol · FEMA 2656 · 3-HYDROXY-2-METHYL-4-PYRANONE · Vetol · Maltol (4 g)
Identifikatoren & physikalische Daten
| CAS No. | 118-71-8 |
|---|---|
| Summenformel | C6H6O3 |
| Durchschnittliche Molmasse | 126,11 g/mol |
| Monoisotopische Masse | 126,03169405 g/mol |
| SMILES | Cc1occc(=O)c1O |
| InChIKey | XPCTZQVDEJYUGT-UHFFFAOYSA-N |
| PubChem CID | 8369 |
| ChEMBL | CHEMBL31422 |
| ChEBI | CHEBI:69438 |
| EC No. | 204-271-8 |
| DTXSID | DTXSID0025523 |
| Lokaler Name | 3-Hydroxy-2-methyl-4-pyron |
Chemische & physikalische Eigenschaften
| XLogP | 0,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 46,5 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 200 |
| pH | pH of 0.5% aqueous solution = 5.35.3 (0.5g/l, H2O) |
| LogP (Verteilungskoeffizient) | log Kow = 0.09 |
| Geruch | Fragrant, caramel-like odorCharacteristic caramel-butterscotch odor and suggestive of a fruity-strawberry aroma in dilute solutionCaramel-like odor, reminiscent of freshly baked cakes |
| Geschmack | Taste characteristics at 200.00 ppm: Sweet, caramellic, cotton candy with fruity, jammy strawberry nuance |
| Color/Form | Monoclinic prisms from chloroform, orthorhombic bypyramidal crystals + monoclinic prisms from 50% alcoholWhite crystalline powder |
| Löslichkeit | 1 to 10 mg/mL at 72 °F (NTP, 1992)In water, 10900 mg/L at 15 °COne gram dissolves in 82 mL water, 80 mL glycerin, 21 mL alcohol, 28 mL propylene glycolFreely soluble in hot water, chloroformsparingly soluble in benzene, ether, petroleum ethersoluble in alkali hydroxides giving yellow solutions10.9 mg/mL at 15 °CSparingly soluble in water, soluble in propylene glycolSoluble (in ethanol)methanol: 50 mg/mL, clear1.2 g/100 mL (25 ºC) |
| Siedepunkt | 199 °F at 760 mmHg (Sublimes) (NTP, 1992)Sublimes at 93 °C205 °C |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | 324 to 327 °F (NTP, 1992)161.5 °C161 - 162 °C160-164 °C(lit.) |
| Dampfdruck | 0.000507 [mmHg]3.26X10-4 mm Hg at 25 °C (extrapolated from reduced pressure boiling point)0.15Pa at 24℃ |
| Physical Description | Maltol is a white crystalline powder with a fragrant caramel-butterscotch odor. pH (5% aqueous solution) 5.3. (NTP, 1992)Other SolidDry PowderLiquidSolid with a fragrant odor like caramel[Merck Index] White powder[Alfa Aesar MSDS]White crystalline powderCaramel-butterscotch aroma |
| Stability/Shelf Life | Stable under recommended storage conditions. |
| Dichte | 1.046 g/mL at 25 °C |
| FEMA | 2656 | MALTOL |
| Brechungsindex | n20/D 1.541 |
| Flammpunkt | 198 °F |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 8.41±0.10(Predicted) |
| Farbe | Clear colorless |
| Geruch | at 5.00 % in benzyl alcohol. sweet caramel cotton candy jam fruity baked bread |
| Explosionsgrenze | 25% |
| Geruchsart | caramellic |
| Biologische Quelle | synthetic |
| Merck | 14,5713 |
| JECFA Number | 1480 |
| BRN | 112169 |
| Henry-Konstante | 7.3×102 mol/(m3Pa) at 25℃, Abraham and Jr. (2019) |
| Kosmetik-Inhaltsstoffe Funktionen | TONICFRAGRANCE |
| InChI | 1S/C6H6O3/c1-4-6(8)5(7)2-3-9-4/h2-3,8H,1H3 |
| InChIKey | XPCTZQVDEJYUGT-UHFFFAOYSA-N |
| SMILES | CC1=C(O)C(=O)C=CO1 |
| LogP (Verteilungskoeffizient) | 2.3 at 25℃ |
| CAS Datenbank | 118-71-8(CAS DataBase Reference) |
| NIST chemische Informationen | 3-Hydroxy-2-methyl-4h-pyran-4-one(118-71-8) |
| EPA chemische Informationen | Maltol (118-71-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 15.5% (303 of 1955) of reports.WarningH302 (84.5%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1955 reports by companies from 20 notifications to the ECHA C&L Inventory.Reported as not meeting GHS hazard criteria per 303 of 1955 reports by companies.There are 18 notifications provided by 1652 of 1955 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: 4H-Pyran-4-one, 3-hydroxy-2-methyl-Regulation (EC) No 1831/2003 (amended)4H-Pyran-4-one, 3-hydroxy-2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 4H-Pyran-4-one, 3-hydroxy-2-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)Status: Active Update: 02-07-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/24008Status: Active Update: 09-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/259043-Hydroxy-2-methyl-4-pyranone: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | Flash point data on this compound are not availablehowever, it is probably combustible. (NTP, 1992) |
| Gefahrenübersicht | No reproductive toxicity observed in rats at doses up to 200 mg/kg[Shepard's Catalog of Teratogenic Agents] A moderate skin irritantCauses changes in renal tubules and weight loss in 90-day oral studies of rats[RTECS] Demonstrates depressant properties in mice (potentiates hexobarbital-induced narcosis and inhibits spontaneous motor activity) |
Anwendungen & Verwendung
Beschreibung
Maltol has a warm, sweet, fruity odor and a jam-like odor in solution. It may be prepared by alkaline hydrolysis of streptomycin salts; also from piperidine to pyromeconic acid and subsequent methylation at the 2 position.
Occurrence
Reported found in the bark of young larch trees (Pinus larix), pine needles (Abies alba), chicory, wood tars and oils, and roasted malt. Also reported found in wheat and rye bread, milk, butter, smoked pork, beer, cocoa, coffee, roasted barley, filberts, peanuts, soybean, beans, tamarind, licorice, sake, malt, dried bonito, clam and cocoa liquor.
Verwenden
A fragrance molecule used in flavor enhancers and fragrances.
Herstellung & Synthese
synthetische
Maltol may be produced synthetically starting from kojic acid . Alternatively, it can be isolated from beechwood tar or from extracts of needles from the genus Abies. Commercially available extracts fromAbies balsamea needles, which are also used as flavor and fragrance materials, usually contain 3–8% maltol. It is used in aroma compositions with a caramel note and as a taste intensifier in, for example, fruit flavors (particularly in strawberry flavor compositions).