3-Hydroxy-2-methyl-4-pyron Chemische Eigenschaften,Einsatz,Produktion Methoden
R-S?tze Betriebsanweisung:
R22:Gesundheitssch?dlich beim Verschlucken.
R38:Reizt die Haut.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R41:Gefahr ernster Augensch?den.
S-S?tze 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.
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.
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).
Definition
ChEBI: A natural product found in Cordyceps sinensis.
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.
Reaktivit?t 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.
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.
LD
50 (chicken, oral): 3.72 g/kg
LD
50 (guinea pig, oral): 1.41 g/kg
LD
50 (mouse, oral): 0.85 g/kg
LD
50 (mouse, SC): 0.82 g/kg
LD
50 (rabbit, oral): 1.62 g/kg
LD
50 (rat, oral): 1.41 g/kg
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.
l?uterung 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.]
Inkompatibilit?ten
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-4-pyron Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
