3-Hydroxy-2-methyl-4-pyron

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H302：Gesundheitsschädlich bei Verschlucken.

• Sicherheit

  P264：Nach Gebrauch gründlich waschen.

  P264：Nach Gebrauch gründlich waschen.

  P270：Bei Gebrauch nicht essen, trinken oder rauchen.

  P301+P312：BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.

  P501：Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

3-Hydroxy-2-methyl-4H-pyran-4-one Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R22:Gesundheitsschädlich beim Verschlucken.
  R38:Reizt die Haut.
  R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
  R41:Gefahr ernster Augenschäden.

• S-Sätze Betriebsanweisung:

  S37:Geeignete Schutzhandschuhe tragen.
  S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
  S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
  S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.

• 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.

• Chemische Eigenschaften

  White, crystalline powder; characteristic caramel-butterscotch odor and suggestive of a fruity-strawberry aroma in dilute solution. Melting range 160–164C. Slightly soluble in water; more soluble in alcohol and propylene glycol.

• Chemische Eigenschaften

  Maltol has a caramel–butterscotch odor and in solution it has a jam-like odor. This compound is also reported to have a suggestive of fruity, strawberry aroma in dilute solution.

• Chemische Eigenschaften

  White crystalline solid with a characteristic, caramel-like odor and taste. In dilute solution it possesses a sweet, strawberry-like or pineapple-like flavor and odor.

• Chemische Eigenschaften

  Maltol occurs in pine needles and the bark of young larch trees. It is produced when cellulose or starch is heated and is a constituent of wood tar oils. It forms crystals (mp 162–164°C) with a caramel-like odor, reminiscent of freshly baked cakes.

• 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.

• Verwenden

  Maltol may be used as an analytical reference standard for the quantification of the analyte in:
  
  • Synthetic and commercial food samples using UV–Vis spectrophotometry with chemometrics methods.
  • Food and beverage matrices using FIA-direct chemiluminescence procedure.
  
  

• Verwenden

  Flavoring agent, to impart "freshly baked" odor and flavor to bread and cakes.

• Definition

  ChEBI: A natural product found in Cordyceps sinensis.

• Vorbereitung Methode

  Maltol is mainly isolated from naturally occurring sources such as beechwood and other wood tars; pine needles; chicory; and the bark of young larch trees. It may also be synthesized by the alkaline hydrolysis of streptomycin salts or by a number of other synthetic methods.

• 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).

• Aroma threshold values

  Detection: 29 ppb

• Taste threshold values

  Taste characteristics at 100 ppm: sweet, caramellic, cotton candy, with jamy fruity and berry notes.

• Synthesis Reference(s)

  The Journal of Organic Chemistry, 45, p. 1109, 1980 DOI: 10.1021/jo01294a037
  Tetrahedron Letters, 17, p. 1363, 1976 DOI: 10.1016/S0040-4039(00)78065-8

• Toxicity evaluation

  The acute oral LD₅₀ in rats was reported to be 2.33 g/kg (1.57-3.09 g/kg) (Moreno, 1974). The acute oral 7-day LD₅₀s in mice, rats and chicks were reported to be 848, 1440 and 3720 mg/kg, respectively (Gralla, Stebbins, Coleman & Delahunt, 1969). Acute oral LD₅₀ values were found to be 550 mg/kg in mice, 1620 mg/kg in rabbits and 1410 mg/kg in guinea-pigs (Dow Chemical Company, 1967). The acute sc LD₅₀ in mice was found to be 820 mg/kg. Sc injection of 400 mg/kg resulted in decreased spontaneous activity, bradycardia, hypothermia, skeletal-muscle relaxation and diminution of pinna, corneal, and ipsilateral flexor reflexes (Aoyagi, Kimura & Murata, 1974). Because of a lack of sample, 5 g/kg could only be applied to one rabbit in the dermal LD₅₀ study, but this dosage was not lethal in the one rabbit (Moreno, 1974).

• Allgemeine Beschreibung

  White crystalline powder with a fragrant caramel-butterscotch odor. pH (5% aqueous solution) 5.3.

• Air & Water Reaktionen

  May be sensitive to prolonged exposure to light and air. Somewhat soluble in water at room temperature. Freely soluble in hot water [Merck]. Slightly soluble in cold water.

• Reaktivität anzeigen

  3-Hydroxy-2-methyl-4H-pyran-4-one is weakly acidic. Reacts with bases. May react with reducing agents. Volatile with steam.

• Brandgefahr

  Flash point data on 3-Hydroxy-2-methyl-4H-pyran-4-one are not available; however, 3-Hydroxy-2-methyl-4H-pyran-4-one is probably combustible.

• Flammability and Explosibility

  Not classified

• Pharmazeutische Anwendungen

  Maltol is used in pharmaceutical formulations and food products as a flavoring agent or flavor enhancer. In foods, it is used at concentrations up to 30 ppm, particularly with fruit flavorings, although it is also used to impart a freshly baked odor and flavor to bread and cakes. When used at concentrations of 5–75 ppm, maltol potentiates the sweetness of a food product, permitting a reduction in sugar content of up to 15% while maintaining the same level of sweetness. Maltol is also used at low levels in perfumery.

• Pharmakologie

  In mice, spontaneous motor activity was depressed by sc injection oi relatively low doses of maltol (75 mg/kg), hexobarbitone sleeping time was prolonged by sc or oral administration of 300 mg/kg, and convulsions induced by pentylenetetrazole or strychnine were inhibited by sc injection of toxic doses (500 mg/kg), but 1 mM concentrations of maltol had no effect on oxygen uptake by slices of the brain cortex of the rat (Aoyagi et al. 1974).

• Sicherheitsprofil

  Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes. A skin irritant. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

• Sicherheit(Safety)

  Maltol is generally regarded as an essentially nontoxic and nonirritant material. In animal feeding studies, it has been shown to be well tolerated with no adverse toxic, reproductive, or embryogenic effects observed in rats and dogs fed daily intakes of up to 200mg/kg body-weight of maltol, for 2 years.The WHO has set an acceptable daily intake for maltol at up to 1mg/kg body-weight.A case of allergic contact dermatitis, attributed to the use of maltol in a lip ointment, has been reported.
  LD₅₀ (chicken, oral): 3.72 g/kg
  LD₅₀ (guinea pig, oral): 1.41 g/kg
  LD₅₀ (mouse, oral): 0.85 g/kg
  LD₅₀ (mouse, SC): 0.82 g/kg
  LD₅₀ (rabbit, oral): 1.62 g/kg
  LD₅₀ (rat, oral): 1.41 g/kg

• Synthese

  By alkaline hydrolysis of streptomycin salts; also from piperdine to pyromeconic acid and subsequent methylation at the 2 position.

• Stoffwechsel

  Maltol is rapidly and extensively metabolized in the dog and excreted by the conjugation pathway common to phenolic compounds. Rennhard (1971) reported that 57% of an iv dose was recovered in 24 hr, 88% of the total excretion occurring in the first 6 hr and 65-70% of the dose administered being recovered as sulphate and glucuronide conjugates

• Lager

  Maltol solutions may be stored in glass or plastic containers. The bulk material should be stored in a well-closed container, protected from light, in a cool, dry place.

• läuterung methode

  It crystallises from CHCl3, toluene, aqueous 50% EtOH or H2O, and is volatile in steam. It can be readily sublimed in a vacuum. It forms a Cu2+ complex. [Beilstein 17 III/IV 5916, 18/1 V 114.]

• Inkompatibilitäten

  Concentrated solutions in metal containers, including some grades of stainless steel, may discolor on storage.

• Regulatory Status

  GRAS listed. Included in the FDA Inactive Ingredients Database (oral solutions and syrups). Included in the Canadian List of Acceptable Non-medicinal Ingredients.

3-Hydroxy-2-methyl-4H-pyran-4-one Upstream-Materialien And Downstream Produkte

3-Hydroxy-2-methyl-4-pyron Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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